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WO2021145356A1 - Composition pharmaceutique destinée au traitement, à la prévention et/ou à l'inhibition de la progression de la myopie - Google Patents

Composition pharmaceutique destinée au traitement, à la prévention et/ou à l'inhibition de la progression de la myopie Download PDF

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Publication number
WO2021145356A1
WO2021145356A1 PCT/JP2021/000953 JP2021000953W WO2021145356A1 WO 2021145356 A1 WO2021145356 A1 WO 2021145356A1 JP 2021000953 W JP2021000953 W JP 2021000953W WO 2021145356 A1 WO2021145356 A1 WO 2021145356A1
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WO
WIPO (PCT)
Prior art keywords
myopia
pharmaceutical composition
administration
ester
salt
Prior art date
Application number
PCT/JP2021/000953
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English (en)
Japanese (ja)
Inventor
隆明 稲葉
圭一 柴垣
功 松岡
弘平 本田
Original Assignee
参天製薬株式会社
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Application filed by 参天製薬株式会社 filed Critical 参天製薬株式会社
Publication of WO2021145356A1 publication Critical patent/WO2021145356A1/fr

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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
    • A61K31/557—Eicosanoids, e.g. leukotrienes or prostaglandins
    • A61K31/558—Eicosanoids, e.g. leukotrienes or prostaglandins having heterocyclic rings containing oxygen as the only ring hetero atom, e.g. thromboxanes
    • 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
    • A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
    • 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
    • A61K9/08—Solutions
    • 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
    • A61K9/10—Dispersions; Emulsions
    • 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
    • A61P27/06—Antiglaucoma agents or miotics
    • 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
    • A61P27/10—Ophthalmic agents for accommodation disorders, e.g. myopia

Definitions

  • the present invention is a pharmaceutical composition for treating myopia, preventing myopia and / or suppressing the progression of myopia, more specifically 4- ⁇ (3S, 5aR, 6R, 7R, 8aS) -6-[(1E, 3R) -4- (2,5-difluorophenoxy) -3-hydroxy-1-buten-1-yl] -7-hydroxyoctahydro-2H-cyclopenta [b] oxepin-3-yl ⁇ butanoic acid or an ester thereof Or related to a pharmaceutical composition comprising salts thereof for the treatment of myopia, prevention of myopia and / or suppression of progression of myopia.
  • Myopia is a type of refractive error, in which light entering the eye from a distance forms an image in front of the retina, making objects appear blurry.
  • myopia when the refractive force of the cornea or crystalline lens is too strong, it is out of focus on the retina when looking at a distance and is in focus in front of the retina (refractive myopia), or axial length. If (the length from the retina to the retina) is elongated and is too long than normal, even if the crystalline lens is thin enough when looking at a distance, it will not be in focus on the retina and will be in focus in front of the retina. It is said that it develops due to the fact that it ends up (axial myopia). Also, the onset of myopia and the rapid progression of myopia at a young age can lead to severe myopia as an adult with visually impaired pathological myopia lesions.
  • Patent Document 1 discloses that atropine (muscarinic receptor antagonist) is useful for the treatment of myopia
  • Patent Document 2 describes tiotropium used for the treatment of chronic obstructive pulmonary disease (COPD). It has been disclosed to be effective in preventing myopia, treating myopia and / or suppressing the progression of myopia.
  • COPD chronic obstructive pulmonary disease
  • Patent Document 3 discloses a huge number of compounds having a strong and continuous effect of lowering intraocular pressure, and one of the compounds is 4- ⁇ (3S, 5aR, 6R, 7R, 8aS) -6-.
  • oxepin-3-yl ⁇ butane The acid is disclosed.
  • An object of the present invention is to find a novel compound useful for treating myopia, preventing myopia and / or suppressing the progression of myopia.
  • the present inventors have a 4- ⁇ (3S, 5aR, 6R, 7R, 8aS) -6-[(3S, 5aR, 6R, 7R, 8aS) -6-[(3S, 5aR, 6R, 7R, 8aS) -6-[ 1E, 3R) -4- (2,5-difluorophenoxy) -3-hydroxy-1-buten-1-yl] -7-hydroxyoctahydro-2H-cyclopenta [b] oxepin-3-yl ⁇ butanoic acid or
  • the present invention has been completed by finding that the ester or a salt thereof suppresses axial length elongation and refractive error.
  • the present invention provides: (1) As an active ingredient, 4- ⁇ (3S, 5aR, 6R, 7R, 8aS) -6-[(1E, 3R) -4- (2,5-difluorophenoxy) -3-hydroxy-1-butene-1 -Il] -7-Hydroxyoctahydro-2H-cyclopentane [b] oxepin-3-yl ⁇ butanoic acid or its esters or salts thereof, for the treatment of myopia, prevention of myopia and / or inhibition of myopia progression Pharmaceutical composition.
  • Myopia includes axial myopia, refractive myopia, pseudomyopia, pathological myopia, simple myopia, extreme myopia, strongest myopia, strong myopia, moderate myopia, weak myopia, and glaucoma (especially juvenile myopia).
  • the pharmaceutical composition according to (1) above which is myopia that has developed, myopia that is at risk of developing glaucoma, or myopia with high ocular pressure.
  • the pharmaceutical composition according to (1) or (2) above which is used for topical ocular administration.
  • composition according to (3) above wherein the topical ocular administration is eye drop administration, ophthalmic ointment administration, intraconjunctival administration, intravitreal administration, subconjunctival administration, subtenon administration, intraconjunctival insertion or eyelid application. .. (5) The pharmaceutical composition according to any one of (1) to (4) above, which is an eye drop, an eye gel, an eye ointment, or an injection.
  • 4-as an active ingredient which has the effects of treating myopia, preventing myopia and / or suppressing the progression of myopia, while suppressing the side effects (mydriasis, etc.) observed with muscarinic receptor antagonists such as atropine.
  • muscarinic receptor antagonists such as atropine.
  • ⁇ (3S, 5aR, 6R, 7R, 8aS) -6-[(1E, 3R) -4- (2,5-difluorophenoxy) -3-hydroxy-1-buten-1-yl] -7-hydroxyocta
  • a pharmaceutical composition comprising hydro-2H-cyclopenta [b] oxepine-3-yl ⁇ butanoic acid or an ester thereof or a salt thereof can be obtained.
  • the ester of the present compound is formed by dehydration condensation of the carboxyl group of the present compound with a monohydric alcohol having 1 to 6 carbon atoms (preferably 1 to 4 carbon atoms, more preferably 1 to 3 carbon atoms).
  • the ester to be used is mentioned.
  • examples of such esters are methyl ester, ethyl ester, n-propyl ester, 2-propanol ester (isopropyl ester), n-butyl ester, isobutyl ester, sec-butyl ester, tert-butyl ester, n-pentyl ester.
  • n-hexyl ester can be mentioned.
  • preferred esters include methyl esters, ethyl esters, n-propyl esters, 2-propanol esters, and most preferably 2-propanol esters.
  • the 2-propanol ester of this compound has the chemical name 2-propanol 4- ⁇ (3S, 5aR, 6R, 7R, 8aS) -6-[(1E, 3R) -4- (2,5-difluorophenoxy)-.
  • 3-Hydroxy-1-butene-1-yl] -7-hydroxyoctahydro-2H-cyclopentane [b] oxepin-3-yl ⁇ is a compound represented by butanoate, and the following formula: It is a compound represented by, and is also called Sepetaprost (CAS Registry Number: 1262873-06-2).
  • 4- ⁇ (3S, 5aR, 6R, 7R, 8aS) -6-[(1E, 3R) -4- (2,5-difluorophenoxy) -3-hydroxy-1-buten-1-yl ] -7-Hydroxyoctahydro-2H-cyclopenta [b] oxepin-3-yl ⁇ butanoic acid or its esters are not only 100% pure, but also their isomers, such as geometric isomers, optical isomers, It may contain tautomers (keto, enol) and the like, and may contain less than 50%, for example.
  • the present compound or an ester thereof may be in the form of a salt, and is not particularly limited as long as it is a pharmaceutically acceptable salt.
  • the salt include salts with inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, nitric acid, sulfuric acid, and phosphoric acid; acetic acid, oxalic acid, fumaric acid, maleic acid, succinic acid, and malic acid.
  • Citric acid tartaric acid, adipic acid, gluconic acid, glucoheptoic acid, glucuronic acid, terephthalic acid, methanesulfonic acid, alanine, lactic acid, horseuric acid, 1,2-ethanedisulfonic acid, isethionic acid, lactobionic acid, oleic acid, gallic acid , Pamoic acid, polygalacturonic acid, stearic acid, tannic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, laurylsulfate, methyl sulfate, naphthalenesulfonic acid, salts with organic acids such as sulfosalicylic acid; sodium , Salts with metals such as potassium, calcium, magnesium; salts with inorganic compounds such as ammonia; and salts with organic amines such as triethylamine, gu
  • the compound or an ester thereof or a salt thereof may take the form of a hydrate or a solvate.
  • the compound or an ester thereof or a salt thereof can be produced by a known method, for example, the methods described in International Publication No. 2011/013651 and International Publication No. 2018/003945.
  • the content of the present compound or an ester thereof or a salt thereof is not particularly limited, but in the case of an eye drop, it is, for example, 0.000001 to 5% (w / v), 0.00001 to 0.05. % (W / v) is more preferable, 0.0001 to 0.01% (w / v) is further preferable, 0.0003 to 0.003% (w / v) is particularly preferable, and 0.001 to 0. 003% (w / v) is most preferable.
  • One aspect of the content of the compound or an ester thereof or a salt thereof in the present invention is 0.002% (w / v).
  • % (w / v) means the mass (g) of the target component contained in 100 mL of the pharmaceutical composition of the present invention
  • % (w / w) is the present invention. It means the mass (g) of the target component contained in 100 g of the pharmaceutical composition of.
  • the value when a salt of the present compound or an ester thereof is contained, the value may be the content of the salt of the present compound or the ester thereof or the content of the compound or the ester thereof.
  • the value thereof is the hydrate of the compound or the ester thereof or a salt thereof or It may be the content of the hydrate, the content of the compound or an ester thereof or a salt thereof, or the content of the compound or an ester thereof.
  • the same shall apply unless otherwise specified.
  • myopia is defined as a refracted state of the eye in which parallel rays entering the eye in an unaccommodated state are imaged in front of the retina.
  • Myopia in the present invention includes all known classifications and definitions of myopia, such as axial myopia, refractive myopia, pseudomyopia, pathological myopia, simple myopia, extreme myopia, strongest myopia, strong myopia.
  • Moderate myopia, weak myopia, myopia with glaucoma (especially juvenile glaucoma), myopia at risk of developing glaucoma, myopia with high eye pressure, etc. preferably axial myopia
  • Examples include extreme myopia, strongest myopia, severe myopia, and myopia developing glaucoma (particularly juvenile glaucoma), more preferably axial myopia.
  • treatment means healing or ameliorating any treatment of myopia or its associated symptoms, such as myopia, particularly refractive myopia and / or axial myopia, and alleviating or suppressing the symptoms associated with myopia. Means. It also includes prevention of recurrence of myopia.
  • prevention means preventing the onset of myopia, delaying the onset of myopia, and reducing the risk of developing myopia.
  • pressing the progression of myopia means delaying the progression of myopia and reducing the progression of myopia.
  • treatment of myopia, prevention of myopia and / or suppression of progression of myopia also includes suppression of axial length extension and / or suppression of refractive error.
  • compositions of the present invention can be widely used regardless of the age of the patient, prevent myopia in children or teenagers with advanced myopia and adults, and / or in teenagers and adults with advanced pediatrics or myopia. It can be used to suppress the progression of myopia.
  • the "patient” means humans and animals such as dogs, cats, horses and the like. Among them, human is preferable.
  • the "therapeutically effective amount” means an amount that brings about a therapeutic effect on myopia and its associated symptoms, or an amount that causes a delay in the progression of myopia, as compared with an untreated subject.
  • the pharmaceutical composition of the present invention may contain a pharmaceutically acceptable active ingredient other than the compound or an ester thereof or a salt thereof.
  • the pharmaceutical composition of the present invention can be orally or parenterally administered.
  • the routes of administration include oral administration, intravenous administration, transdermal administration, topical ocular administration (eg, ophthalmic administration, ointment administration, intraconjunctival administration, intravitreal administration, subconjunctival administration, subconjunctival administration, intraconjunctival insertion, etc. Eyelid application) and the like.
  • the pharmaceutical composition of the present invention is prepared by mixing the compound or an ester thereof or a salt thereof with one or more pharmaceutically acceptable additives, for example, tablets, capsules, granules, powders, troches, syrups.
  • pharmaceutically acceptable additives for example, tablets, capsules, granules, powders, troches, syrups.
  • Conventional methods in the art for the desired form of oral preparations such as agents, emulsions, suspensions, or parenteral preparations such as eye drops, eye gels, eye ointments, injections, suppositories, nasal preparations.
  • Preferred dosage forms of the pharmaceutical composition of the present invention include eye drops, eye gels, eye ointments and injections.
  • a desired eye drop When using an eye drop, a desired eye drop can be prepared by adding the compound or an ester thereof or a salt thereof to purified water, a buffer solution, etc., stirring the mixture, and then adjusting the pH with a pH adjuster.
  • additives commonly used in eye drops can be used as needed, and the additives include tonicity agents, buffering agents, surfactants, stabilizers, preservatives, solubilizers, and the like. Can be mentioned.
  • the pH of the eye drops may be within the range allowed for the ophthalmic preparation, preferably in the range of pH 4 to 8, and more preferably in the range of pH 5 to 7.
  • the base When used as an eye ointment, it can be prepared using a general-purpose base, and examples of the base include white petrolatum and liquid paraffin.
  • a bulking agent such as lactose, crystalline cellulose, starch, vegetable oil and the like
  • examples of the lubricant include magnesium stearate and talc
  • examples of the binder include hydroxypropyl cellulose and polyvinylpyrrolidone.
  • examples of the disintegrant include carboxymethyl cellulose calcium, low-substituted hydroxypropyl methyl cellulose and the like
  • examples of the coating agent include hydroxypropyl methyl cellulose, macrogol, silicon resin and the like
  • examples of the film agent include gelatin film and the like.
  • the dosage of the pharmaceutical composition of the present invention can be appropriately changed according to the dosage form, the patient's symptoms, age, weight, the age at which myopia develops, the judgment of a doctor, and the like.
  • the dosage is not particularly limited as long as it is sufficient to achieve the desired medicinal effect, but one to several drops per dose is taken from 1 to 1 to 1 day. It can be instilled several times (for example, 1 to 8 times). It can also be used when wearing contact lenses.
  • Example 1 Myopia progression (axial length extension and refractive error) suppression test using a guinea pig myopia model (1) The effect of sepetaprost on myopia progression (axial length extension and refractive error) was evaluated according to the following method. (Sample preparation) After dissolving Sepetaprost in purified water containing a solubilizer, a 0.002% Sepetaprost solution was prepared as a sample using a general-purpose method. As a control, saline was used.
  • a lens (goggles) was prepared by cutting the tip of the bottom portion of a test tube having a diameter of 18 mm by 10 mm and adhering it to one side of a magic tape (about 20 mm square) having a hole having an appropriate diameter in the center with an adhesive.
  • a control group 10 per group.
  • 10 ⁇ L of 0.002% sepetaprost solution was applied to the right eye of each guinea pig every day for 14 days until the 13th day. It was administered by eye drops 6 times a day.
  • 10 ⁇ L of physiological saline was instilled into the right eye of each guinea pig.
  • the left eye of all guinea pigs was instilled with 10 ⁇ L of physiological saline 6 times a day for 14 days from the 0th day to the 13th day. Guinea pigs were bred under normal breeding conditions.
  • Difference in refraction (D) right refraction (D) -left refraction (D)
  • Refractive error suppression rate (%) (difference in refraction in the 1-0.002% sepetaprost solution administration group / difference in refraction in the control group) ⁇ 100
  • Table 2 shows the average values of the difference in axial length and the difference in refraction between the control group and the 0.002% sepetaprost solution administration group.
  • Table 3 shows the axial length elongation inhibition rate and the refractive error inhibition rate in the 0.002% sepetaprost solution administration group.
  • the axial length elongation inhibition rate was 79% and the refractive error inhibition rate was 91% in the 0.002% sepetaprost solution administration group.
  • Example 2 Myopia progression (axial length extension and refractive error) suppression test using a guinea pig myopia model (2) According to the following method, the effects of sepetaprost and timolol maleic acid on myopia progression (axial length extension and refractive error) were evaluated and the effects of lowering intraocular pressure were evaluated.
  • Sample preparation After dissolving Sepetaprost in purified water containing a solubilizer, a 0.002% Sepetaprost solution was prepared as a sample using a general-purpose method.
  • timoptol (registered trademark) ophthalmic solution which is a 0.5% timolol maleic acid solution, was used as a sample.
  • saline was used as a control.
  • 10 ⁇ L of 0.002% sepetaprost solution was applied to the right eye of each guinea pig every day for 16 days until the 15th day. It was administered by eye drops 6 times a day.
  • Difference in axial length and axial length elongation suppression rate from before the start of instillation administration, difference in refractive error and refractive error suppression rate from before the start of instillation administration, and difference in intraocular pressure from before the start of instillation administration on the 15th day Calculated by the following formula. The calculation was performed in Microsoft Excel based on the measured values.
  • Axial length elongation inhibition rate (%) (difference in axial length between 1-0.002% sepetaprost solution administration group (or difference in axial length between 0.5% timolol maleic acid solution administration group) / control group (Difference in axial length) x 100
  • Difference in refraction (D) Right refraction on day 14-Right refraction (D) before the start of instillation
  • Refractive error suppression rate (%) (difference in refraction of 1-0.002% sepetaprost solution administration group (or difference in refraction of 0.5% timolol maleic acid solution administration group) / difference in refraction of control group Difference) x 100
  • Table 5 shows the average values of the difference in axial length, the difference in refraction, and the difference in intraocular pressure between the control group, the 0.002% sepetaprost solution-administered group, and the 0.5% timolol maleic acid solution-administered group.
  • Table 6 shows the axial length elongation inhibition rate and the refractive error inhibition rate of the 0.002% sepetaprost solution administration group and the 0.5% timolol maleic acid solution administration group.
  • the intraocular pressure lowering effect was observed in the 0.002% sepetaprost solution administration group and the 0.5% timolol maleic acid solution administration group.
  • the axial length elongation inhibition rate was 53% and the refractive error inhibition rate was 51% in the 0.002% sepetaprost solution administration group, but in the 0.5% timolol maleic acid solution administration group. No effect of suppressing axial length extension and refractive error was observed.
  • sepetaprost was shown to strongly suppress axial length extension and refractive error. Therefore, sepetaprost is useful in the treatment of myopia, prevention of myopia and / or suppression of progression of myopia.
  • the pharmaceutical composition of the present invention is 4- ⁇ (3S, 5aR, 6R, 7R, 8aS) -6-[(1E, 3R) -4- (2,5-difluorophenoxy) -3-hydroxy-1-butene.
  • -1-yl] -7-Hydroxyoctahydro-2H-cyclopenta [b] oxepin-3-yl ⁇ butanoic acid or an ester thereof or a salt thereof suppresses axial length elongation and refractive error to treat myopia. It is useful for preventing myopia and / or suppressing the progression of myopia.

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  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
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  • Animal Behavior & Ethology (AREA)
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  • Dispersion Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

L'invention fournit une composition pharmaceutique destinée au traitement, à la prévention et/ou à l'inhibition de la progression de la myopie qui contient, en tant que principe actif, soit un acide ４－｛（３Ｓ，５ａＲ，６Ｒ，７Ｒ，８ａＳ）－６－［（１Ｅ，３Ｒ）－４－（２，５－difluorophénoxy）－３－hydroxy－１－butène－１－yl］－７－hydroxyoctahydro－２Ｈ－cyclopenta［ｂ］oxépine－３－yl｝butanoïque ou un ester de celui-ci, soit un sel de ceux-ci.
PCT/JP2021/000953 2020-01-15 2021-01-14 Composition pharmaceutique destinée au traitement, à la prévention et/ou à l'inhibition de la progression de la myopie WO2021145356A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023204297A1 (fr) * 2022-04-22 2023-10-26 参天製薬株式会社 Composition destinée à un usage ophtalmique contenant du sépétaprost

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005289814A (ja) * 2002-04-12 2005-10-20 Mei Co Ltd 近視矯正手術のための医薬
WO2011013651A1 (fr) * 2009-07-28 2011-02-03 小野薬品工業株式会社 Composé bicyclique et utilisation de celui-ci à des fins médicales
WO2012102357A1 (fr) * 2011-01-27 2012-08-02 小野薬品工業株式会社 Composé bicyclique et utilisation associée à des fins médicales
WO2019124489A1 (fr) * 2017-12-21 2019-06-27 参天製薬株式会社 Médicament comprenant une combinaison de sépétaprost et d'agoniste d'ep2

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005289814A (ja) * 2002-04-12 2005-10-20 Mei Co Ltd 近視矯正手術のための医薬
WO2011013651A1 (fr) * 2009-07-28 2011-02-03 小野薬品工業株式会社 Composé bicyclique et utilisation de celui-ci à des fins médicales
WO2012102357A1 (fr) * 2011-01-27 2012-08-02 小野薬品工業株式会社 Composé bicyclique et utilisation associée à des fins médicales
WO2019124489A1 (fr) * 2017-12-21 2019-06-27 参天製薬株式会社 Médicament comprenant une combinaison de sépétaprost et d'agoniste d'ep2

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023204297A1 (fr) * 2022-04-22 2023-10-26 参天製薬株式会社 Composition destinée à un usage ophtalmique contenant du sépétaprost

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