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WO2025046475A1 - Dérivé hétérocyclique destiné à être utilisé dans le traitement de la dermatite atopique - Google Patents

Dérivé hétérocyclique destiné à être utilisé dans le traitement de la dermatite atopique Download PDF

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Publication number
WO2025046475A1
WO2025046475A1 PCT/IB2024/058343 IB2024058343W WO2025046475A1 WO 2025046475 A1 WO2025046475 A1 WO 2025046475A1 IB 2024058343 W IB2024058343 W IB 2024058343W WO 2025046475 A1 WO2025046475 A1 WO 2025046475A1
Authority
WO
WIPO (PCT)
Prior art keywords
atopic dermatitis
alkyl
chemical formula
pruritus
present
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.)
Pending
Application number
PCT/IB2024/058343
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English (en)
Korean (ko)
Inventor
이지은
공민정
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.)
JW Pharmaceutical Corp
Original Assignee
JW Pharmaceutical Corp
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 JW Pharmaceutical Corp filed Critical JW Pharmaceutical Corp
Publication of WO2025046475A1 publication Critical patent/WO2025046475A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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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
    • A61K31/33—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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4436—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a heterocyclic ring having sulfur as a ring hetero atom
    • 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
    • A61P17/04—Antipruritics
    • 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]
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems

Definitions

  • the present invention relates to a heterocyclic derivative for treating atopic dermatitis, and more particularly, to a pharmaceutical composition for preventing or treating atopic dermatitis or pruritus, comprising a compound having the heterocyclic derivative structure of the present invention as an active ingredient.
  • Atopic dermatitis is an inflammatory skin eczematous disease, which is accompanied by severe itching and is characterized by chronic relapse (N Engl J Med., 2021, 384, 1136-43).
  • the cause of atopic dermatitis is a complex interaction of various genetic and environmental factors as well as damage to the skin barrier, skin microbiota imbalance, and immune dysregulation, in which Th2 cells are activated by dendritic cells and innate lymphocytes of the epithelial layer stimulated by external antigens that penetrate through the damaged skin barrier (Dermatol Sin., 2019, 37, 3-11).
  • Activated T cells secrete inflammatory and pruritic cytokines such as IL-4, IL-13, and IL-31, and activate the JAK/STAT signaling system, a downstream signal transducer, thereby inhibiting the production of filaggrin, which plays a skin protective role, and inducing skin barrier damage due to pruritus, thereby aggravating skin inflammation (Allergy, 2018, 73, 1881–1891).
  • cytokines such as IL-4, IL-13, and IL-31
  • JAK/STAT signaling system a downstream signal transducer
  • One object of the present invention is to provide a pharmaceutical composition for preventing or treating atopic dermatitis or pruritus, comprising the compound of the present invention, a stereoisomer thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof, or a solvate thereof as an active ingredient.
  • Another object of the present invention is to provide a method for preventing or treating atopic dermatitis or pruritus, comprising administering to a subject in need thereof a compound of the present invention, a stereoisomer thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof or a solvate thereof.
  • Another object of the present invention is to provide a method for preventing or treating atopic dermatitis or pruritus, comprising administering to a subject in need thereof a compound of the present invention, a stereoisomer thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof or a solvate thereof.
  • the present invention provides a use of the compound of the present invention, a stereoisomer thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof or a solvate thereof for treatment.
  • Another object of the present invention is to provide a use of the compound of the present invention, a stereoisomer thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof or a solvate thereof for the manufacture of a medicament for the prevention or treatment of atopic dermatitis or pruritus.
  • the compound of the present invention reduces the expression of inflammation-related cytokine genes, thereby reducing the epidermal thickness in inflamed tissues and having excellent anti-pruritic efficacy, and therefore can be usefully used as a composition for the prevention and treatment of atopic dermatitis and pruritus.
  • Figure 1 schematically shows an experimental method for confirming the effect of the compound of the present invention in a histamine-induced acute pruritus animal model.
  • Figure 2 schematically shows an experimental method for confirming the effect of the compound of the present invention in an IL-31-induced acute pruritus animal model.
  • FIG. 3 shows the results of confirming the number of scratching behaviors in a histamine-induced acute itch animal model.
  • Figure 4 shows the results of confirming the number of scratching behaviors in an IL-31-induced acute itch animal model.
  • FIG. 5 schematically illustrates an experimental method for confirming the effect of the compound of the present invention in an atopic dermatitis animal model.
  • FIG. 6 illustrates the results of H&E staining of skin tissue in the first experiment of an atopic dermatitis animal model.
  • FIG. 7 illustrates the results of confirming the thickness of dermal tissue in the first experiment of an atopic dermatitis animal model.
  • FIG. 8 illustrates the results of H&E staining of skin tissue in the second experiment of an atopic dermatitis animal model.
  • FIG. 9 illustrates the results of confirming the thickness of dermal tissue in the second experiment of an atopic dermatitis animal model.
  • FIG. 10 illustrates the results of confirming the number of scratching behaviors in the first experiment of an atopic dermatitis animal model.
  • FIG. 11 illustrates the results of confirming the number of scratching behaviors in the second experiment of an atopic dermatitis animal model.
  • FIG. 12 illustrates the results of confirming the expression of genes related to inflammation and itching in the first experiment of an atopic dermatitis animal model.
  • Fig. 13 is the result of confirming the gene expression related to inflammation and itching in the second experiment of an atopic dermatitis animal model. [Best mode for carrying out the invention] This is described in detail as follows.
  • R b is H, C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkyl, C 1-6 alkylcarbonyl-C 1-6 alkyl, C 2-7 alkenyl, amino, or aminoC 1-6 alkyl, and at least one H of R b may be independently substituted with F, Br, Cl, or I
  • R 2 and R 3 are each independently F, Br, Cl, or I.
  • R a O
  • R b is unsubstituted C 1-3 alkyl.
  • C mn (wherein m and n are each independently an integer of 1 or more) means the number of carbons, for example, 'C 1-6 alkyl' means alkyl having 1 to 6 carbons.
  • alkyl means a straight-chain or branched-chain saturated hydrocarbon group represented by C n H 2n+1 .
  • alkyl examples include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, n-pentyl, sec-pentyl, tert-pentyl, isopentyl, sec-isopentyl, neo-pentyl, n-hexyl, and the like.
  • alkenyl means an unsaturated hydrocarbon group including at least one carbon-carbon double bond in the alkyl.
  • alkoxy means a monovalent group derived from a straight-chain or branched-chain saturated hydrocarbon moiety represented by OC n H 2n+1 .
  • alkoxy include, but are not limited to, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, pentoxy, hexoxy, etc.
  • the compound represented by the chemical formula I may be a compound represented by the following chemical formula II. [Chemical Formula II]
  • the compound represented by chemical formula II corresponds to compound 1 of the present invention, and is also named N-(2-chloro-6-(4-chlorophenoxy)pyridin-4-yl)-4-(methylsulfonyl)-3,4-dihydro-2H-thieno[3,2-g]chromene-7-carboxamide.
  • pharmaceutically acceptable means a compound which is suitable for use in contact with the tissues of a subject (e.g., a human) without excessive toxicity, irritation, allergic response or other problems or complications and having a reasonable benefit/risk ratio and which is within the scope of sound medical judgment.
  • the pharmaceutically acceptable salts of the present invention can be prepared by conventional methods known to those skilled in the art.
  • the compound according to any one of the above (1) to (3) of the present invention reduces the expression of inflammation-related cytokine genes, thereby reducing the epidermal thickness in inflamed tissues and has excellent anti-pruritic efficacy, and therefore can be usefully used as a composition for preventing and treating atopic dermatitis and pruritus.
  • composition comprising a heterocyclic derivative compound, a treatment method using the same, and use thereof
  • the present invention relates to a compound according to any one of the above (1) to (3), a stereoisomer thereof, a pharmaceutically acceptable salt thereof, a hydrate or a solvate thereof, A pharmaceutical composition comprising the compound as an active ingredient is provided.
  • the present invention provides a pharmaceutical composition for preventing or treating atopic dermatitis or pruritus, comprising a compound according to any one of (1) to (3) above, a stereoisomer thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof, or a solvate thereof as an active ingredient.
  • prevention means any act of inhibiting or delaying the onset of a disease by administering a compound according to any one of (1) to (3) above, a stereoisomer thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof, or a solvate thereof; or a pharmaceutical composition comprising the same.
  • treatment means any act of improving or beneficially changing the symptoms of a subject suspected of having a disease or having an onset of a disease by administering a compound according to any one of (1) to (3) above, a stereoisomer thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof, or a solvate thereof; or a pharmaceutical composition comprising the same.
  • atopic dermatitis is an allergic disease that is worse in dry climates due to an abnormality in the stratum corneum, which acts as a protective barrier on the outermost part of the skin.
  • the main symptoms are severe itching, dry skin, rash, oozing, scabs, and scales, and are mainly accompanied by chronic skin inflammation.
  • the cause of atopic dermatitis is mainly genetic and has been found to be related to immune responses, and in addition, it is thought to be caused by a complex interaction of dry skin, a characteristic of easily feeling itchy skin compared to normal people, infection by bacteria, viruses, and fungi, emotional factors, and environmental factors.
  • the antipruritic activity and the preventive and therapeutic activity for atopic dermatitis of a compound according to any one of (1) to (3) of the present invention, a stereoisomer thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof, or a solvate thereof were confirmed.
  • the pharmaceutical composition of the present invention is characterized by reducing the expression of one or more cytokines selected from the group consisting of IL-4, IL-5, IFN- ⁇ , H4R, IL-17, and IL-31.
  • the pharmaceutical composition of the present invention suppresses the expression of inflammatory cytokines, reduces the thickness of the skin epidermis induced by atopic dermatitis, and reduces itching, so it can be usefully used for the prevention or treatment of atopic dermatitis and itching.
  • the pharmaceutical composition of the present invention can be manufactured in a unit dose form or by being placed in a multi-dose container by formulating it using a pharmaceutically acceptable carrier and excipient.
  • the formulation can be prepared by a conventional method used in formulation in the art or by a method disclosed in Remington's Pharmaceutical Science ( 19th ed., 1995). It can be manufactured and can be formulated into various preparations according to each disease or component.
  • a person skilled in the art can administer the pharmaceutical composition of the present invention in an amount that can obtain the maximum effect with the minimum amount without side effects by taking all of the above factors into consideration, and this can be easily determined by a person skilled in the art to which the present invention belongs.
  • the pharmaceutical composition of the present invention can exhibit excellent effects even when used alone, but can be additionally used in combination with various methods such as hormone therapy and drug therapy in order to increase therapeutic efficiency.
  • the present invention relates to a compound according to any one of (1) to (3), a stereoisomer thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof, or a solvate thereof, Or, the present invention provides a method for preventing or treating atopic dermatitis or pruritus, comprising a step of administering a pharmaceutical composition comprising the same to a subject in need thereof.
  • administration means introducing a predetermined substance into a subject by an appropriate method.
  • the "subject” means all animals, such as rats, mice, and livestock, including humans, which have developed or may develop atopic dermatitis or pruritus, and may specifically be mammals including humans, but is not limited thereto.
  • the method for preventing or treating atopic dermatitis or pruritus of the present invention may be a method for administering a therapeutically effective amount of a compound according to any one of (1) to (3) above, a stereoisomer thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof, or a solvate thereof.
  • terapéuticaally effective amount in the present invention means an amount sufficient to treat a disease at a reasonable benefit/risk ratio applicable to medical treatment and not causing side effects, which can be determined by those skilled in the art based on factors including the patient's sex, age, weight, health status, type and severity of the disease, activity of the drug, sensitivity to the drug, administration method, administration time, administration route, excretion rate, treatment period, drugs used in combination or simultaneously, and other factors well known in the medical field.
  • a specific therapeutically effective amount for a specific patient will depend on various factors including the type and degree of response to be achieved, the specific composition including whether other agents are used depending on the case, the patient's age, weight, general health status, sex and diet, administration time, administration route and excretion rate of the composition, treatment period, drugs used together or simultaneously with the specific composition, and various other factors. It is preferable to apply differently according to factors and similar factors well known in the pharmaceutical field.
  • the method for preventing or treating atopic dermatitis or pruritus of the present invention includes not only treating the disease itself before the onset of symptoms, but also inhibiting or avoiding the symptoms thereof by administering a compound according to any one of (1) to (3) above, a stereoisomer thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof or a solvate thereof, or a pharmaceutical composition comprising the same.
  • the prophylactic or therapeutic dosage of a specific active ingredient will vary depending on the nature and severity of the disease or condition, and the route by which the active ingredient is administered. The dosage and frequency of administration will vary depending on the age, weight, and response of the individual patient.
  • the method for preventing or treating atopic dermatitis or pruritus of the present invention may further include administering a therapeutically effective amount of an additional active agent helpful in preventing or treating the disease together with the compound according to any one of (1) to (3), a stereoisomer thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof, or a solvate thereof.
  • the additional active agent may exhibit a synergistic or additive effect together with the compound according to any one of (1) to (3), a stereoisomer thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof, or a solvate thereof.
  • the present invention relates to a compound according to any one of (1) to (3), a stereoisomer thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof, or a solvate thereof, or a pharmaceutical agent comprising the same for preventing or treating atopic dermatitis or pruritus.
  • the present invention provides a use of a composition.
  • the present invention provides a use of a compound according to any one of (1) to (3) above, a stereoisomer thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof or a solvate thereof, or a pharmaceutical composition comprising the same, for the manufacture of a medicament for preventing or treating atopic dermatitis or pruritus.
  • a compound according to any one of (1) to (3) above, a stereoisomer thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof or a solvate thereof may be mixed with a pharmaceutically acceptable excipient, a diluent, a carrier, etc., and may be manufactured into a complex preparation together with other active agents to have a synergistic effect.
  • the acute pruritus animal model a standardized pruritus model, was used to confirm the acute pruritus inhibitory effect of compound 1 (N-(2-chloro-6-(4-chlorophenoxy)pyridin-4-yl)-4-(methylsulfonyl)-3,4-dihydro-2H-thieno[3,2-g]chromene-7-carboxamide) (Figs. 1 and 2).
  • the drug was used at 75 mg/kg of compound 1 prepared with excipients (10% DMSO, 20% PEG400, 10% Tween80, 60% 0.1 M NaHCO3 ) .
  • Example 2 Evaluation of the efficacy of the compound of the present invention in an atopic dermatitis animal model The effect of compound 1 on atopic dermatitis was confirmed using the EC (Epicutaneous) OVA sensitization animal model, which is an atopic dermatitis animal model (Fig. 5). Specifically, the drug was used at 75 mg/kg of compound 1 prepared with excipients (10% DMSO, 20% PEG400, 10% Tween80, 60% 0.1 M NaHCO3 ) .
  • each animal was placed in an opaque acrylic cage, a video was recorded for 1 hour, and the number of times the animal scratched using the hind legs was measured to evaluate the itch behavior.
  • the thickness of the epidermis tissue of the group administered 75 mg/kg of compound 1 was reduced by about 12.5% (1st, Figs. 6 and 7) and about 8.5% (2nd, Figs. 8 and 9) compared to the vehicle administration group.
  • the number of scratching behaviors was significantly reduced by about 84.2% (1st, Fig.

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

Abstract

La présente invention concerne des dérivés hétérocycliques destinés à être utilisés dans le traitement de la dermatite atopique et, plus spécifiquement, une composition pharmaceutique destinée à prévenir ou à traiter la dermatite atopique ou le prurit, comprenant, en tant que principe actif, un composé présentant une structure de dérivé hétérocyclique, un stéréoisomère de celui-ci, un sel pharmaceutiquement acceptable de celui-ci, un hydrate de celui-ci ou un solvate de celui-ci.
PCT/IB2024/058343 2023-08-29 2024-08-28 Dérivé hétérocyclique destiné à être utilisé dans le traitement de la dermatite atopique Pending WO2025046475A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR20230114040 2023-08-29
KR10-2023-0114040 2023-08-29

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WO2025046475A1 true WO2025046475A1 (fr) 2025-03-06

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014196793A1 (fr) * 2013-06-05 2014-12-11 C&C Research Laboratories Dérivés hétérocycliques et leur utilisation
US9556139B2 (en) * 2008-06-25 2017-01-31 Array Biopharma Inc. 6-substituted phenoxychroman carboxylic acid derivatives
KR20170081708A (ko) * 2014-12-02 2017-07-12 주식회사 씨앤드씨신약연구소 헤테로환형 유도체 및 이의 용도
KR20230038125A (ko) * 2021-09-10 2023-03-17 주식회사 프롬바이오 Stat3 저해제로서 헤테로아릴 유도체 화합물 및 이의 용도
KR20230104086A (ko) * 2021-10-27 2023-07-07 주식회사 휴켐바이오 신규한 트리사이클릭 유도체 화합물 및 이의 용도

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9556139B2 (en) * 2008-06-25 2017-01-31 Array Biopharma Inc. 6-substituted phenoxychroman carboxylic acid derivatives
WO2014196793A1 (fr) * 2013-06-05 2014-12-11 C&C Research Laboratories Dérivés hétérocycliques et leur utilisation
KR20170081708A (ko) * 2014-12-02 2017-07-12 주식회사 씨앤드씨신약연구소 헤테로환형 유도체 및 이의 용도
KR20230038125A (ko) * 2021-09-10 2023-03-17 주식회사 프롬바이오 Stat3 저해제로서 헤테로아릴 유도체 화합물 및 이의 용도
KR20230104086A (ko) * 2021-10-27 2023-07-07 주식회사 휴켐바이오 신규한 트리사이클릭 유도체 화합물 및 이의 용도

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