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WO2005053672A1 - Remede contre le prurit comportant du cilomilaste ou un sel de celui-ci comme principe actif - Google Patents

Remede contre le prurit comportant du cilomilaste ou un sel de celui-ci comme principe actif Download PDF

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Publication number
WO2005053672A1
WO2005053672A1 PCT/JP2004/018427 JP2004018427W WO2005053672A1 WO 2005053672 A1 WO2005053672 A1 WO 2005053672A1 JP 2004018427 W JP2004018427 W JP 2004018427W WO 2005053672 A1 WO2005053672 A1 WO 2005053672A1
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WO
WIPO (PCT)
Prior art keywords
pruritus
eye
cilomilast
therapeutic agent
ointment
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.)
Ceased
Application number
PCT/JP2004/018427
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English (en)
Japanese (ja)
Inventor
Daisuke Shii
Tomoko Oda
Hideki Miyake
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.)
Santen Pharmaceutical Co Ltd
Original Assignee
Santen Pharmaceutical Co Ltd
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 Santen Pharmaceutical Co Ltd filed Critical Santen Pharmaceutical Co Ltd
Publication of WO2005053672A1 publication Critical patent/WO2005053672A1/fr
Anticipated expiration legal-status Critical
Ceased 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
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0048—Eye, e.g. artificial tears
    • 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
    • A61K31/275—Nitriles; Isonitriles
    • A61K31/277—Nitriles; Isonitriles having a ring, e.g. verapamil
    • 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
    • A61P17/04—Antipruritics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents

Definitions

  • Antipruritic agent containing cilomilast or a salt thereof as an active ingredient
  • the present invention relates to a therapeutic agent for pruritus containing cilomilast or a salt thereof as an active ingredient.
  • the pruritic receptors present in the epidermis-dermis junction of the skin and mucous membranes are stimulated by a transmitter (pruritic substance), and the stimulus is transmitted to the central nervous system and is felt as itching.
  • a transmitter for example, histamine, kinin, bile salts, substance P, and prostaglandins are widely known as mediators that induce itch. It is presumed that histamine and other mediators released from mast cells and the like are involved in the appearance of allergic factors, and it is known that antihistamines have stronger effects than antiallergy agents. .
  • pruritus for example, itching that occurs in humans and animals, pruritus in the skin, pruritus in the ears and nose, and pruritus in the body are known.
  • Eye pruritus is a disease that causes itching of eyes, eyelids, eyelid edges, etc. due to pollen, dust, mites, mold, pet hair, contact lenses, cosmetics, etc. This causes conjunctival hyperemia, and conjunctival papillae reddens and proliferates. In severe cases, lesions appear on the cornea and sclera, and may progress to spring catarrhal.
  • cilomilast chemical name: cis-1 [4-cyano-4- (3-cyclopentyloxy-14-methoxyphenyl) cyclohexane-1-carbon] It is described that a compound such as an acid is useful in mediating or inhibiting the enzyme activity of phosphodiesterase IV, and is effective as a therapeutic agent for allergic and inflammatory diseases, especially asthma.
  • a compound such as an acid is useful in mediating or inhibiting the enzyme activity of phosphodiesterase IV, and is effective as a therapeutic agent for allergic and inflammatory diseases, especially asthma.
  • the compounds described in the above patent specifications show efficacy against itch, which is the most major symptom associated with allergic diseases. Disclosure of the invention
  • cilomilast described in the above patent specification has various pharmacological properties as a medicament. Although it is effective, finding a new pharmacological effect against itch is an interesting issue.
  • the present inventors have conducted intensive studies to search for new pharmaceutical uses of the above-mentioned compounds, and found that the above-mentioned compounds exert an excellent anti-pruritic effect in an ocular pruritus inhibition test using an albumin-induced ocular pruritus model. This led to the completion of the present invention.
  • the present invention relates to a therapeutic agent for pruritus comprising cilomilast or a salt thereof as an active ingredient.
  • Typical pruritus to which the therapeutic agent for pruritus according to the present invention is applied is pruritus of the eye.
  • a preferred dosage form of the therapeutic agent for pruritus according to the present invention is a liquid, more preferably an eye drop.
  • the concentration of the active ingredient in the eye drops is preferably from 0.01 to 3% (w / V).
  • Another preferred form of the therapeutic agent for antipruritus according to the present invention is an external preparation, more preferably an ointment such as an eye ointment.
  • Silomilast which is an active ingredient of the therapeutic agent for pruritus according to the present invention, is represented by the chemical name of cis- [4-cyano-14- (3-cyclopentyloxy-4-methoxyphenyl) cyclohexane-1-carbonic acid]. It is represented by the following chemical structural formula.
  • the salt of cilomilast is not particularly limited as long as it is a pharmaceutically acceptable salt.
  • Salts with inorganic acids such as hydrochloric acid, nitric acid and sulfuric acid, and salts with organic acids such as acetic acid, fumaric acid, maleic acid, succinic acid and tartaric acid Salts, and salts with alkali metals such as sodium, potassium, and calcium or alkaline earth metals are also included. More preferred salts are the sodium and potassium salts.
  • a quaternary ammonium salt of cilomilast is also included in the salt of the present invention.
  • geometric isomers, optical isomers, tautomers, and polymorphs of silomilast are also included in the scope of the present invention. Note that cilomilast may be in the form of a hydrate or a solvate.
  • the therapeutic agent for pruritus according to the present invention is characterized by It has an excellent antipruritic effect on pruritus, and has therapeutic and inhibitory effects on pruritus such as eye pruritus, skin pruritus, otitis pruritus and systemic pruritus that occur in humans and animals.
  • the therapeutic agent for pruritus according to the present invention is preferably used as a therapeutic agent for ocular pruritus.
  • Eye pruritus is a disease in which the eyes, eyelids, eyelid margins, etc. become itchy due to pollen, dust, mites, mold, pet hair, contact lenses, cosmetics, eye trauma, etc. Itching is associated with allergic unilateral conjunctivitis, spring catarrh, atopic keratoconjunctivitis, infectious keratoconjunctivitis, blepharitis, dry eye, conjunctivitis, corneal herpes, corneal herpes, etc. and ophthalmic surgery. Includes those that develop.
  • the therapeutic agent for pruritus according to the present invention can be formulated into a single preparation or a combined preparation by using a commonly used technique, if necessary, by adding a pharmaceutically acceptable additive.
  • the therapeutic agent for pruritus according to the present invention can be administered parenterally or orally.
  • oral preparations include liquid preparations for internal use (eg, elixirs, syrups, pharmaceutically acceptable solutions, suspensions, and emulsions), solid preparations for internal use (eg, tablets (sublingual tablets, Disintegrating tablets), pills, capsules (including hard capsules, soft capsules, gelatin capsules, micro capsules), powders, granules, troches and the like.
  • Parenteral preparations include, for example, liquid preparations (eg, injections (subcutaneous injections, intravenous injections, intramuscular injections, intraperitoneal injections, instillations, etc.), eye drops (eg, 7J eye drops ( 7-based ophthalmic solution, aqueous suspension ophthalmic solution, viscous ophthalmic solution, solubilized ophthalmic solution, etc.), non-aqueous ophthalmic solution (non-aqueous ophthalmic solution, non-aqueous suspension ophthalmic solution, etc.)), etc.), external preparations (for example, Ointments (eg, B gorge ointment), gels, creams, compresses, patches, liniments, etc., sprays, inhalants, sprays, nasal drops, suppositories (eg, rectal suppositories, vaginal suppositories) ) And the like. These preparations may be release controlling agents such as immediate release preparations and sustained release
  • Liquid preparations for oral administration are prepared, for example, by dissolving, suspending or emulsifying the active ingredient in a commonly used diluent (for example, purified water, ethanol or a mixture thereof).
  • a commonly used diluent for example, purified water, ethanol or a mixture thereof.
  • the liquid preparation for internal use may further contain a wetting agent, a suspending agent, an emulsifier, a sweetening agent, a flavoring agent, a fragrance, a preservative, a buffering agent and the like.
  • Solid preparations for internal use as oral preparations include, for example, excipients (e.g., lactose, Ninitol, glucose, microcrystalline cellulose, starch, etc.), binders (eg, hydroxypropylcellulose, polyvinylpyrrolidone, magnesium aluminate metasilicate, etc.), disintegrants (eg, calcium cellulose glycolate, etc.), lubricants ( For example, it is mixed with a stabilizer such as magnesium stearate, etc.), a stabilizer, a solubilizing agent (glutamic acid, aspartic acid, etc.) and the like, and prepared according to a conventional method.
  • the solid preparation for internal use may be coated with a coating agent (for example, sucrose, gelatin, hydroxypropylcellulose, hydroxypropylmethylcellulose phthalate, etc.) if necessary.
  • the coating layer may be two or more layers.
  • An external preparation as a parenteral preparation is prepared by a known method or a commonly used formulation.
  • ointments are prepared by triturating or melting the active ingredient as a base.
  • the ointment base is selected from known or commonly used ones.
  • higher fatty acids or higher fatty acid esters eg, adipic acid, myristic acid, palmitic acid, stearic acid, oleic acid, adipic acid ester, myristic acid ester, palmitic acid ester, stearic acid ester, oleic acid ester, etc.
  • waxes eg, beeswax, spermaceti, ceresin, etc.
  • surfactants eg, polyoxyethylene alkyl ether phosphate, etc.
  • higher alcohols eg, cetanol, stearyl alcohol, setosteryl alcohol, etc.
  • silicone oil eg, For example, dimethylpolysiloxane, etc.
  • hydrocarbons eg, hydrophilic petrolatum, white petrolatum, purified lanolin, liquid paraffin, etc.
  • glycols eg, ethylene glycol, diethylene glycol, propylene
  • glycols eg, ethylene glycol
  • Gels are prepared, for example, by melting the active ingredient in a base.
  • the gel base is selected from those known or commonly used. For example, lower alcohols (eg, ethanol, isopropyl alcohol, etc.), gelling agents (eg, carboxymethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, ethylcellulose, etc.), neutralizing agents (eg, triethanol Amines, diisopropanolamines, etc.), surfactants (eg, monos Polyethylene glycol theate), gums, water, absorption enhancers, and rash preventives are used alone or as a mixture of two or more.
  • the gel may further contain a preservative, an antioxidant, a flavoring agent and the like.
  • Creams are prepared, for example, by melting or emulsifying the active ingredient in a base.
  • the cream base is selected from known or commonly used ones. For example, higher fatty acid esters, lower alcohols, hydrocarbons, polyhydric alcohols (for example, propylene glycol, 1,3-butylene glycol, etc.), higher alcohols (2-hexyldecanol, cetanol, etc.), emulsifiers (poly) Those selected from oxyethylene alkyl ethers, fatty acid esters, etc.), water, absorption promoters, and rash inhibitors are used alone or in combination of two or more.
  • the cream may further contain a preservative, an antioxidant, a flavoring agent, and the like.
  • a poultice is prepared, for example, by melting an active ingredient in a base, forming a kneaded product, and spreading and applying the mixture on a support.
  • the compress base is selected from known or commonly used ones. For example, thickeners (eg, polyacrylic acid, polyvinylpyrrolidone, gum arabic, starch, gelatin, methylcellulose, etc.), wetting agents (eg, urea, glycerin, propylene glycol, etc.), fillers (eg, kaolin, oxidized) One selected from zinc, talc, calcium, magnesium, etc.), water, a dissolution aid, a tackifier, and a rash inhibitor are used alone or in combination of two or more.
  • the poultice may further contain a preservative, an antioxidant, a flavoring agent and the like.
  • a patch is prepared by, for example, melting an active ingredient in a base and spreading and applying the composition on a support.
  • the base for the patch is selected from known or commonly used ones. For example, those selected from polymer bases, oils and fats, higher fatty acids, tackifiers, and rash inhibitors are used alone or in combination of two or more.
  • the patch may further contain a preservative, an antioxidant, a flavoring agent, etc.
  • the liniment include an active ingredient such as water, alcohol (eg, ethanol, polyethylene glycol, etc.), higher fatty acid, glycerin, seggen, It is prepared by dissolving, suspending or emulsifying alone or in combination of two or more selected from emulsifiers and suspending agents.
  • the liniment may further contain a preservative, an antioxidant, a flavoring agent and the like.
  • Sprays and sprays are prepared by known or commonly used formulations. This include, for example, buffers other than commonly used diluents that provide isotonicity with stable IJ such as sodium bisulfite, for example, isotonic such as sodium chloride, sodium citrate or citric acid. An agent may be contained.
  • Inhalants include aerosols, PJs: powders to be taken or liquids for inhalation.
  • the liquid preparation for inhalation may be in the form of being dissolved or suspended in water or another suitable medium before use.
  • Liquid preparations for inhalation include preservatives (eg, benzalkonium chloride, paraben, etc.), coloring agents, buffering agents (eg, sodium phosphate, sodium acetate, etc.), and isotonic agents (eg, sodium chloride, concentrated glycerin, etc.) It is prepared by using a thickener (for example, caliperoxy vinyl polymer), an absorption enhancer and the like as required.
  • Powders for inhalation include lubricants (eg, stearic acid and its salts), binders (eg, starch, dextrin, etc.), excipients (eg, lactose, cellulose, etc.), coloring agents, preservatives (eg, , Benzalkonium chloride, paraben, etc.) and absorption enhancers, if necessary.
  • a nebulizer eg, an atomizer, a nebulizer
  • a powder inhaler is usually used for administering a powder for inhalation.
  • Parenteral injections include solutions, suspensions, emulsions, and solid injections that are dissolved or suspended in a solvent before use. Injections are used, for example, by dissolving, suspending or emulsifying the active ingredient in a solvent.
  • a solvent for example, distilled water for injection, physiological saline, vegetable oil, alcohols such as propylene glycol, polyethylene glycol, ethanol and the like and a combination thereof are used.
  • Injectables may further contain stabilizers, solubilizing agents (eg, glutamic acid, aspartic acid, polysorbate 80 (registered trademark), etc.), suspending agents, emulsifiers, soothing agents, buffers, preservatives, etc. May be included.
  • Injectables are preferably prepared by sterilization in the final step or prepared by an aseptic procedure.
  • a sterile solid preparation for example, a freeze-dried product is prepared and sterilized or sterilized before use. It can also be used after dissolving in distilled water or other solvents.
  • Preferred dosage forms for using the therapeutic agent for pruritus according to the present invention as a therapeutic agent for ocular pruritus are eye drops, eye ointments, tablets and the like, more preferably eye drops or eye ointments. These can be prepared using commonly used techniques. For example, eye drops are isotonic as an additive It can be prepared by appropriately mixing agents, buffers, pH regulators, solubilizers, thickeners, stabilizers, preservatives and the like. In addition, a stable eye drop can be obtained by adding a pH adjuster, a thickener, a dispersant, and the like to suspend the drug.
  • tonicity agent examples include glycerin, propylene glycol, sodium chloride, potassium chloride, sorbitol, mannitol and the like.
  • buffer examples include phosphoric acid, phosphate, citric acid, acetic acid, ⁇ -aminocaproic acid and the like.
  • pH regulator examples include hydrochloric acid, citric acid, phosphoric acid, acetic acid, sodium hydroxide, potassium hydroxide, boric acid, borax, sodium carbonate, sodium hydrogen carbonate and the like.
  • solubilizers examples include polysorbate 80, polyoxetylene hardened castor oil 60, macrogol 400, and the like.
  • thickener and dispersant examples include cellulosic polymers such as hydroxypropylmethylcellulose and hydroxypropyl cellulose, polyvinyl alcohol, and polyvinylpyrrolidone.
  • stabilizer examples include edetic acid and sodium edetate And so on.
  • preservatives examples include general-purpose sorbic acid, potassium sorbate, benzalkonium chloride, benzethonium chloride, methyl parahydroxybenzoate, propyl benzoate, pill, chlorobutanol, and the like. Can be used in combination.
  • the pH is preferably set to 4.0 to 8.5, and the osmotic pressure ratio is preferably set to around 1.0.
  • the present invention also relates to a method for treating pruritus, which comprises administering cilomilast or a salt thereof to a patient in a therapeutically effective amount.
  • the dosage of the active ingredient when used as a therapeutic agent for pruritus can be appropriately selected depending on the condition, age, dosage form, etc., but for oral preparations, preferably 1 mg to 100 mg, more preferably 5 mg to 30 mg. mg may be administered one to several times a day (eg, one to three times).
  • the eye drops are preferably 0.001 -10% (w / v), more preferably 0.01 to 3% (w / v) at a single dose: ⁇ Several drops may be instilled one to several times a day (eg, 1 to 8 times).
  • the eye ointment is preferably administered at a concentration of 0.001 to 10% (w / w), more preferably 0.01 to 3% (w / w) once to several times a day (for example, 1 to 4 times). Times).
  • the dose varies depending on various conditions, so that a dose smaller than the above dose may be sufficient, or may be required beyond the range.
  • ovalbumin (20 pg / mL) was dissolved in a physiological saline solution, and active sensitization was performed by injecting 100 g of each of them into the 6-week-old male Hartley guinea pig under the conjunctiva of both eyes. On the 14th day after the sensitization, 1.0% (W / V) saline solution of ovalbumin was instilled into both eyes by 10 L / eye.
  • test compound a solution in which 0.1% (WZV) and 0.5% (/) of the present compound were suspended in 1.5% Tween80 was prepared. Each eye was instilled at a dose of 10 pL / eye to each eye. In addition, 1.5% Teen80 was used as a control.
  • Table 1 shows the eye-drawing behavior suppression rate (average value) for the control calculated according to the following equation. The number of cases is 8 eyes each.
  • An eye drop having the following formulation is prepared using a commonly used method.
  • An eye ointment having the following formulation is prepared using a commonly used method.
  • cilomilast exerts an excellent pruritus-suppressing effect in an albumin-induced ocular pruritus model, it is useful as a therapeutic agent for any pruritus such as ocular pruritus, skin pruritus and systemic pruritus.

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  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Ophthalmology & Optometry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Medicinal Preparation (AREA)

Abstract

La présente invention vise à la découverte d'un nouvel effet pharmacologique (une utilisation médicinale) du cilomilaste. Grâce à son excellent effet anti-prurit, le cilomilaste est utile en tant que remède contre le prurit de tout type tels que le prurit oculaire, le prurit cutané et le prurit systémique.
PCT/JP2004/018427 2003-12-04 2004-12-03 Remede contre le prurit comportant du cilomilaste ou un sel de celui-ci comme principe actif Ceased WO2005053672A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2003-405702 2003-12-04
JP2003405702 2003-12-04

Publications (1)

Publication Number Publication Date
WO2005053672A1 true WO2005053672A1 (fr) 2005-06-16

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PCT/JP2004/018427 Ceased WO2005053672A1 (fr) 2003-12-04 2004-12-03 Remede contre le prurit comportant du cilomilaste ou un sel de celui-ci comme principe actif

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010120841A1 (fr) * 2009-04-17 2010-10-21 Alcon Research, Ltd. Compositions ophtalmiques aqueuses contenant des agents thérapeutiques anioniques

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07508508A (ja) * 1992-04-02 1995-09-21 スミスクライン・ビーチャム・コーポレイション アレルギーおよび炎症疾患の治療用化合物
JP2001520196A (ja) * 1997-10-17 2001-10-30 スミスクライン・ビーチャム・コーポレイション 化合物の抗掻痒活性のための新規な利用

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07508508A (ja) * 1992-04-02 1995-09-21 スミスクライン・ビーチャム・コーポレイション アレルギーおよび炎症疾患の治療用化合物
JP2001520196A (ja) * 1997-10-17 2001-10-30 スミスクライン・ビーチャム・コーポレイション 化合物の抗掻痒活性のための新規な利用

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
FERRER L. ET AL: "Clinical anti-inflammatory efficacy of arofylinne, a new selective phosphodiesterase-4 inhibitor, in dogs with atopic dermatitis.", THE VETERINARY RECORD, vol. 145, no. 7, 1999, pages 191 - 194, XP002987760 *
HANIFIN J. M. ET AL: "Type 4 Phosphodiesterase Inhibitors Have Clinical and In Vitro Anti-inflammatory Effects in Atopic Dermatitis.", J. INVEST. DERMATOL., vol. 107, no. 1, 1996, pages 51 - 56, XP000915565 *
SCHMIDT B. M. W. ET AL: "The phosphodiesterase 4 inhibitor roflumilast is effective in the treatment of allergic rhinitis.", J. ALLERGY. CLIN. IMMUNOL., vol. 108, no. 4, 2001, pages 530 - 536, XP008016318 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010120841A1 (fr) * 2009-04-17 2010-10-21 Alcon Research, Ltd. Compositions ophtalmiques aqueuses contenant des agents thérapeutiques anioniques
JP2012524094A (ja) * 2009-04-17 2012-10-11 アルコン リサーチ， リミテッド アニオン性治療剤を含む水性眼用組成物
US8785497B2 (en) 2009-04-17 2014-07-22 Alcon Research, Ltd. Aqueous ophthalmic compositions containing anionic therapeutic agents
AU2010236505B2 (en) * 2009-04-17 2014-08-21 Alcon Research, Ltd. Aqueous ophthalmic compositions containing anionic therapeutic agents

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