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WO2024162814A1 - Nouveau composé bicyclique et son utilisation - Google Patents

Nouveau composé bicyclique et son utilisation Download PDF

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Publication number
WO2024162814A1
WO2024162814A1 PCT/KR2024/001580 KR2024001580W WO2024162814A1 WO 2024162814 A1 WO2024162814 A1 WO 2024162814A1 KR 2024001580 W KR2024001580 W KR 2024001580W WO 2024162814 A1 WO2024162814 A1 WO 2024162814A1
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Prior art keywords
cancer
carboxamide
disease
dodecyl
compound
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English (en)
Korean (ko)
Inventor
박석주
유지훈
김다롱
전희전
곽윤나
홍기범
도현주
김성환
이정열
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Provibio Co Ltd
Daegu Gyeongbuk Medical Innovation Foundation
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Provibio Co Ltd
Daegu Gyeongbuk Medical Innovation Foundation
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Publication of WO2024162814A1 publication Critical patent/WO2024162814A1/fr
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    • A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
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Definitions

  • the present invention relates to a novel bicyclic compound and uses thereof, and more particularly, to uses of the compound of formula 1 and its salts for treating or preventing cancer or autoimmune diseases.
  • the present invention relates to a composition comprising the compound and its salts as active ingredients for treating, preventing or improving cancer or autoimmune diseases.
  • the present invention relates to a method for treating, preventing or improving cancer or autoimmune diseases by administering the compound and its salts to a subject.
  • cancer is still a major cause of death worldwide.
  • cancer treatments such as targeted anticancer drugs and immunotherapy drugs, are being developed, there is still a very high demand for drugs that are safe for the human body and have excellent cancer treatment properties.
  • Autoimmunity refers to an inappropriate response of the immune system to autoantigens, causing damage to cells or tissues through humoral immunity, cell-mediated immunity, or both.
  • Autoimmune diseases are related to molecules, cells, and tissues targeted by the autoimmune response, and can be systemic or specific to specific organs depending on the distribution of the target antigen.
  • SLE systemic lupus erythematosus
  • RA rheumatoid arthritis
  • MS multiple sclerosis
  • autoimmune anemia insulin-dependent diabetes mellitus
  • Graves' disease are organ-specific autoimmune diseases.
  • the inventors of the present invention recognized the problems of the above-mentioned prior art and conducted numerous trials and errors to find a compound having excellent treatment, prevention or improvement effects on cancer or autoimmune diseases. As a result, they developed a bicyclic compound of chemical formula 1 and completed the present invention.
  • the purpose of the present invention is to provide a compound or a salt thereof having excellent treatment, prevention or improvement effects on cancer or autoimmune diseases.
  • X1, X2, X3 and X4 are each independently carbon or nitrogen.
  • the term "each independently" as used in the present invention means that two or more substituents are individually defined and may be different from each other or may be the same.
  • X1, X2, X3 and X4 may be the same or different from each other.
  • X1, X2, X3 and X4 may all be carbon.
  • X1 may be nitrogen
  • X2, X3 and X4 may be carbon.
  • X2 may be nitrogen
  • X1, X3 and X4 may be carbon.
  • Y is -CO- or -CH 2 CO-.
  • -CO- represents a ketone group.
  • R1, R2, R3, R4 and R5 are each independently H, -OH, -SH, halogen, -NO 2 , -NH 2 , -CF 3 , C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C10 arylalkyl, C5-C10 aryl, C3-C10 alkylaryl, C3-C10 cycloalkyl, C3-C10 heteroaryl, C3-C10 heterocycloalkyl, -OR6, -COR6, -SR6 or -NHR6.
  • R1, R2, R3, R4 and R5 may be the same or different.
  • R1 and R2, R2 and R3, R3 and R4, or R4 and R5 may be combined with each other to form a C5-C10 aryl or a C2-C10 heteroaryl.
  • R1 and R2 may be combined with each other to form a C5-C10 aryl or a C2-C10 heteroaryl.
  • R2 and R3 may be combined with each other to form a C5-C10 aryl or a C2-C10 heteroaryl.
  • R3 and R4 may be combined with each other to form a C5-C10 aryl or a C2-C10 heteroaryl.
  • R4 and R5 may be combined with each other to form a C5-C10 aryl or a C2-C10 heteroaryl.
  • the heteroaryl formed by combining R1 and R2, R2 and R3, R3 and R4, or R4 and R5 preferably has a nitrogen atom.
  • R6 is H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C10 arylalkyl, C5-C10 aryl, C3-C10 alkylaryl, C3-C10 cycloalkyl, C3-C10 heteroaryl or C3-C10 heterocycloalkyl.
  • R7 is C8-C12 alkyl, C8-C12 alkenyl or C8-C12 alkynyl.
  • R1 to R7 may be independently substituted with C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C5-C10 aryl, C3-C10 cycloalkyl, C3-C10 heteroaryl, or C3-C10 heterocycloalkyl.
  • alkyl, alkenyl, and alkynyl are intended to include both straight-chain (also referred to as linear) and branched-chain (also referred to as branched).
  • halogen as used in the present invention means fluorine, chlorine, bromine or iodine.
  • alkoxy as used in the present invention means O-alkyl.
  • hetero as used in the present invention means a hetero atom selected from oxygen, nitrogen and sulfur.
  • cycloalkyl as used in the present invention means alkyl forming a ring.
  • heterocycloalkyl as used in the present invention means cycloalkyl in which a heteroatom is contained within the ring.
  • arylalkyl used in the present invention means alkyl having an aryl group.
  • alkylaryl used in the present invention means aryl having an alkyl group.
  • salt used in the present invention can be prepared by a method conventional in the art, and for example, can be formed by forming a salt of an inorganic acid such as hydrochloric acid, hydrogen bromide, sulfuric acid, sodium bisulfate, phosphoric acid, or carbonic acid, or a salt of these acids together with an organic acid such as formic acid, acetic acid, oxalic acid, benzoic acid, citric acid, tartaric acid, gluconic acid, gestic acid, fumaric acid, lactobionic acid, salicylic acid, or acetylsalicylic acid (aspirin), or can form a metal salt thereof by reacting with an alkali metal ion such as sodium or potassium, or can form another type of salt by reacting with an ammonium ion, but is not limited thereto.
  • an inorganic acid such as hydrochloric acid, hydrogen bromide, sulfuric acid, sodium bisulfate, phosphoric acid, or carbonic acid
  • organic acid such as
  • the compound according to the present invention or its salt includes isomers, solvates or crystalline forms.
  • the term "isomer” as used in the present invention includes stereoisomers, enantiomers, diastereomers, tautomers, geometric isomers, etc.
  • solvate as used in the present invention means an aggregate or complex of the compound of the present invention and one or more solvent molecules, wherein the solvent includes, but is not limited to, water, isopropanol, ethanol, methanol, dimethyl sulfoxide, ethyl acetate, acetic acid, and ethanolamine.
  • the term “hydrate” as used in the present invention means a solvate in which the solvent molecule is water.
  • crystal form as used in the present invention means a form in which identical molecules form different crystal structures.
  • the compound of formula 1 according to the present invention may be selected from the group consisting of:
  • Another aspect of the present invention provides a pharmaceutical composition for treating or preventing cancer or an autoimmune disease, comprising a compound represented by chemical formula 1 or a pharmaceutically acceptable salt thereof.
  • treatment means all cases in which cancer or an autoimmune disease is improved, reversed, or cured by administration of a composition according to the present invention.
  • prevention used in the present invention means all things that suppress, delay, prevent, etc. the occurrence or recurrence of cancer or autoimmune disease by administration of the composition according to the present invention.
  • the cancer may be, but is not limited to, liver cancer, colon cancer, pancreatic cancer, colon cancer, small intestine cancer, stomach cancer, lung cancer, brain cancer, bone cancer, melanoma, breast cancer, sclerosing adenoma, uterine cancer, cervical cancer, head and neck cancer, esophageal cancer, thyroid cancer, parathyroid cancer, kidney cancer, sarcoma, prostate cancer, urethral cancer, bladder cancer, blood cancer, lymphoma, or fibroadenoma.
  • the above autoimmune diseases include systemic lupus erythematosus (SLE), glomerulitis, ankylosing spondylitis, myastenia gravis, rheumatoid arthritis (RA), multiple sclerosis (MS), systemic sclerosis, pernicious anemia, autoimmune anemia, inflammatory bowel disease, insulin-dependent diabetes mellitus (IDDM), type 1 diabetes, Graves' disease, Graves' hyperthyroidism, Kikuchi's disease, hemophagocytic lymphohistiocytosis, adult onset Still's disease, Behcet's disease. disease), IgG4-associated diseases, psoriasis, asthma, or transplant rejection, but are not limited to these.
  • SLE systemic lupus erythematosus
  • glomerulitis glomerulitis
  • ankylosing spondylitis myastenia gravis
  • RA rheumatoid arthritis
  • MS multiple sclerosis
  • the pharmaceutical composition of the present invention comprises an effective amount of the compound, an isomer thereof, a solvate, a hydrate, a crystal form thereof, or a salt thereof, and can be administered to a subject in need of prevention or treatment of cancer or an autoimmune disease.
  • the term "administration" means physically introducing a composition into a subject using any of a variety of methods and delivery systems known to those of ordinary skill in the art.
  • the administration may be, for example, oral, or intravenous, intramuscular, subcutaneous, intraperitoneal, spinal or other parenteral administration, such as injection or infusion, but is not limited thereto.
  • the number of times the administration may be performed may be, for example, single, multiple, and over one or more extended periods of time.
  • the pharmaceutical composition of the present invention may be formulated as a preparation for oral or parenteral administration according to the route of administration as described above.
  • subject as used herein includes a human or any non-human animal, which non-human animal may be a vertebrate, such as a primate, dog, cow, horse, pig, rodent, such as a mouse, rat, guinea pig, and the like. As used herein, the “subject” is used interchangeably with “individual” and “patient”.
  • the subject to whom the compound or composition according to the present invention is administered may be a cancer patient, or a cancer patient suffering from an autoimmune disease or at a high risk of developing an autoimmune disease.
  • the subject to whom the compound or composition according to the present invention is administered may be a patient suffering from an autoimmune disease, or a patient suffering from cancer or at a high risk of developing an autoimmune disease.
  • the effective amount may be a "therapeutically effective amount” or a “prophylactically effective amount.”
  • therapeutically effective amount means any amount that, when the drug or therapeutic agent is used alone or in combination with other therapeutic agents, can exhibit a decrease in the severity of disease symptoms, an increase in the frequency and duration of disease symptom-free periods, or a prevention of impairment or disability due to disease affliction.
  • prophylactically effective amount means any amount that inhibits the occurrence or recurrence of a disease in a subject.
  • the level of the effective amount can be determined depending on factors such as the severity of the disease, age, sex, activity of the drug, sensitivity to the drug, time of administration, route of administration and excretion rate, duration of treatment, concomitant medications, and other factors well known in the medical field.
  • the dosage of the pharmaceutical composition may vary depending on the age, sex, weight, administration route, severity of disease, etc. of the subject, and specifically, depending on the symptoms of the subject, 0.1 to 100 mg/kg of the composition of the present invention may be administered once or several times a day, or at intervals of several days to several months.
  • the pharmaceutical composition may further comprise suitable carriers, excipients and diluents commonly used in the manufacture of pharmaceutical compositions.
  • Carriers, excipients and diluents that may be included in the composition may be, but are not limited to, for example, lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starch, acacia gum, alginate, gelatin, calcium phosphate, calcium silicate, cellulose, methyl cellulose, microcrystalline cellulose, polyvinyl pyrrolidone, water, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate and mineral oil.
  • the pharmaceutical composition may be administered in combination with other therapeutic agents.
  • the pharmaceutical composition of the present invention and the other therapeutic agents may be administered simultaneously, sequentially, or individually.
  • the other therapeutic agents may be drugs such as compounds, proteins, etc. that have preventive, therapeutic, and improving effects on cancer or autoimmune diseases, but are not limited thereto.
  • the pharmaceutical composition may be formulated to be administered simultaneously, sequentially, or separately with another therapeutic agent.
  • the compound, its isomer, solvate, hydrate, crystalline form, or salt thereof and the other therapeutic agent may be administered simultaneously in one formulation, or may be administered simultaneously, sequentially, or separately in separate formulations.
  • the compound, its isomer, solvate, hydrate, crystalline form, or salt thereof and the other therapeutic agent included in the pharmaceutical composition of the present invention may be formulated separately in separate containers, or may be formulated together in the same container.
  • the compound, its isomer, solvate, hydrate, crystalline form, or salt thereof and the other therapeutic agent included in the pharmaceutical composition of the present invention may be the same or different from each other in terms of pharmaceutically effective amount, administration time, administration interval, administration route, treatment period, etc.
  • Another aspect of the present invention provides a method for treating or preventing cancer or an autoimmune disease, comprising administering to a subject a compound represented by chemical formula 1 or a salt thereof.
  • the compound or its salt may be administered to the subject simultaneously, sequentially, or separately with other agents.
  • spontaneous administration means administering the compound or its salt and the other therapeutic agent at the same time as one preparation, or means administering the compound or its salt and the other therapeutic agent at the same time as separate preparations, in which case the routes of administration may be different.
  • the above “sequential" administration means administering the compound or its salt and the other therapeutic agent relatively sequentially, allowing for the shortest possible time between administrations.
  • the above “separate” administration means administering the compound or its salt and other therapeutic agents at regular intervals of time.
  • Another aspect of the present invention provides a food composition for improving or preventing cancer or an autoimmune disease, comprising a compound represented by chemical formula 1 or a food-chemically acceptable salt thereof.
  • each term has the same meaning as described above in the composition unless specifically mentioned.
  • improvement means any act in which the degree of cancer or autoimmune disease is reduced, improved, or progression is delayed by administration of the composition according to the present invention.
  • the above food may be a health functional food.
  • health functional food refers to a food manufactured and processed in the form of tablets, capsules, powders, granules, liquids, and pills using raw materials or ingredients that have functionality useful to the human body.
  • functionality refers to obtaining a useful effect for health purposes such as regulating nutrients or physiological actions for the structure and function of the human body.
  • the food composition according to the present invention can be manufactured by a method commonly used in the art, and can be manufactured by adding raw materials and ingredients commonly added in the art during the manufacturing process.
  • it has the advantage of not having side effects that may occur when taking drugs for a long period of time because it uses food as a raw material, and since it is highly portable, the food composition of the present invention can be taken as a supplement to enhance or improve the therapeutic effect of cancer.
  • the amount of the compound, its isomer, solvate, hydrate, crystal form or its food-wise acceptable salt included as an effective ingredient in the food composition according to the present invention may be suitably determined depending on the intended use (prevention, improvement or therapeutic treatment).
  • the compound of the present invention or its food-wise acceptable salt may be included in an amount of 0.001 to 20 wt%, 0.001 to 15 wt% or 0.001 to 10 wt% in the composition.
  • 0.01 to 2 g, specifically 0.02 to 2 g, more specifically 0.3 to 1 g may be added based on 100 mL.
  • the amount may be used below the above range.
  • the content of the compound according to the present invention or a food-wise acceptable salt thereof added to the food composition can be appropriately increased or decreased as needed.
  • the food composition of the present invention may further contain additional ingredients in addition to the compound or a food-wise acceptable salt thereof to enhance efficacy.
  • the above food composition may be in any one dosage form selected from the group consisting of a pill, a tablet, a granule, a powder, a capsule, and a liquid solution.
  • the type of the food is not particularly limited.
  • foods to which the substance can be added include meat, sausage, bread, chocolate, candy, snacks, confectionery, pizza, ramen, other noodles, gum, dairy products including ice cream, various soups, beverages, tea, drinks, alcoholic beverages, and vitamin complexes, and include all foods in the conventional sense.
  • the food composition of the present invention may contain various flavoring agents or natural carbohydrates as additional ingredients, like conventional foods.
  • the natural carbohydrates are monosaccharides such as glucose and fructose, disaccharides such as maltose and sucrose, polysaccharides such as dextrin and cyclodextrin, and sugar alcohols such as xylitol, sorbitol and erythritol.
  • a natural sweetener such as thaumatin and stevia extract, or a synthetic sweetener such as saccharin and aspartame can be used.
  • the food composition of the present invention is a beverage composition
  • the liquid component other than containing the compound or a food-wise acceptable salt thereof as an essential component in the indicated ratio there is no special limitation on the liquid component other than containing the compound or a food-wise acceptable salt thereof as an essential component in the indicated ratio, and various flavoring agents or natural carbohydrates, etc. may be contained as additional components like a conventional beverage.
  • the bicyclic compound of chemical formula 1 or a salt thereof according to the present invention has an excellent effect of killing cancer cells or inhibiting tumor growth and proliferation, and is highly safe for the human body. Therefore, it can be usefully utilized for the prevention, treatment, or improvement of cancer.
  • the bicyclic compound of chemical formula 1 or a salt thereof according to the present invention exhibits a strong immunosuppressive function by not only inhibiting the proliferation of T cells but also inducing the death of B cells, and therefore can be usefully used for the treatment or prevention of autoimmune diseases that form autoantibodies in addition to transplant rejection.
  • Figure 1 shows the level of apoptosis when the compound of the present invention was treated at a concentration of 30 ⁇ M in the B cell lymphoma cell line SU-DLH-8. On the X-axis, C indicates the control (DMSO).
  • Figure 2 shows the level of apoptosis when the cervical cancer cell line HeLa was treated with the compound of the present invention at a concentration of 30 ⁇ M.
  • C indicates the control group (DMSO).
  • the compounds of the present invention were prepared according to the following reaction scheme. Compounds having different substituents were also prepared through similar steps, but are not all specified in this specification. Those skilled in the art can easily prepare compounds having different substituents by referring to the representative examples below.
  • Benzoic acid (1 eq), amine (1.1 eq), EDCI (1.1 eq), DMAP (0.1 eq), and TEA (2.2 eq) having various substituents were added to 1 ml of dichloromethane (DCM) and stirred at room temperature for 6 hours. 50 ml of water was added and dichloromethane (60 ml) was added to separate the organic layer, which was dried over Na 2 SO 4 , filtered, and concentrated under reduced pressure. Then, the residue was purified using column chromatography (EA 5%) to obtain the target compound as a result.
  • DCM dichloromethane
  • the human B-cell lymphoma cell line SU-DLH-8 (ATCC, Cat. # CRL-2961) purchased from ATCC was cultured in RPMI-1640 medium containing 10% FBS, 100 U/mL penicillin, and 100 ⁇ g/mL streptomycin. Each cell culture was collected, centrifuged at 1,300 rpm for 5 minutes, the supernatant was removed, and the cells were resuspended in the same medium. 90 ⁇ L per well was dispensed into a 96-well plate (Costar 96 well cell culture plate, Corning) and finally treated to obtain the conditions shown in Table 1.
  • Each plate was treated with 10 ⁇ L of the compound according to the present invention or the control (DMSO) at various concentrations (0, 10, 30, 50 ⁇ M), and then cultured in a 5% CO 2 incubator at 37°C for 48 hours. Thereafter, 10 ⁇ L of CCK-8 was added to each well, and cultured again in a 5% CO 2 incubator at 37°C for 4 hours, and the absorbance was measured at 450 nm to show the relative cell viability (%) for cells not treated with the drug, as shown in Table 2.
  • the values listed in Table 2 indicate the relative cell viability in the groups treated with each compound at various concentrations, when the cell viability in the group treated with the control (DMSO) is 100%.
  • the human prostate cancer cell line LNCaP the human breast cancer cell line MCF-7, the human lung cancer cell line A549, and the human colon cancer cell line HCT-116 were provided from the Korea Cell Line Bank and cultured in RPMI-1640 medium containing 10% FBS.
  • the human cervical cancer cell line HeLa and the human liver cancer cell line SK-HEP-1 both provided from the Korea Cell Line Bank, were cultured in MEM and DMEM medium containing 10% FBS, 100 U/mL penicillin, and 100 ⁇ g/mL streptomycin, respectively.
  • each stabilized cell was recovered through Trypsin-EDTA treatment, centrifuged at a speed of 1,200 rpm for 3 minutes, the supernatant was removed, resuspended in the same medium, and dispensed at 100 ⁇ L per well into a 96-well plate (Costar 96 well cell culture plate, Corning) to finally achieve the conditions in Table 3.
  • SK-HEP-1 Human Hepatic Adenocarcinoma
  • DMEM with 10% FBS, 100U/mL penicillin, 100 ⁇ g/mL streptomycin 1 ⁇ 10 4 cells/well
  • HeLa Human Cervical Carcinoma
  • MEM with 10% FBS, 100U/mL penicillin, 100 ⁇ g/mL streptomycin 5 ⁇ 10 3 cells/well
  • LNCaP Human Prostate Adenocarcinoma
  • RPMI 10% FBS 2.5 ⁇ 10 4 cells/well MCF-7 (Human Breast Cancer) 2 ⁇ 10 4 cells/well A549 (Human Lung Carcinoma) 1.5 ⁇ 10 4 cells/well HCT-116 (Human Colorectal Carcinoma) 3.5 ⁇ 10 4 cells/well
  • Human B-cell lymphoma cell line SU-DLH-8 (ATCC, Cat. # CRL-2961) purchased from ATCC was cultured in RPMI-1640 medium containing 10% FBS, 100 U/mL penicillin, and 100 ⁇ g/mL streptomycin. Each cell culture was collected, centrifuged at 1,300 rpm for 5 minutes, and the supernatant was removed. The cells were resuspended in the same medium and dispensed into 6-well plates at 1.5 mL per well to achieve the final conditions of Table 10. The plates were treated with 30 ⁇ M compounds 50, 110, 114, and 119 or the control group (DMSO), and then cultured at 37°C for 48 hours in a 5% CO 2 incubator.
  • DMSO control group
  • control or compound-treated cells were collected and fluorescent stained for Annexin V/PI, and the results were analyzed via flow cytometry.
  • the degree of apoptosis occurrence was analyzed via flow cytometry, and the sum of the percentages (%) of cells located at Annexin V High /PI High , Annexin V High /PI Low , and Annexin V Low /PI High in the data is represented as a bar graph in Figure 1.
  • the human cervical cancer cell line HeLa obtained from the Korea Cell Line Bank was cultured in MEM medium containing 10% FBS, 100 U/mL penicillin, and 100 ⁇ g/mL streptomycin. After that, each stabilized cell was recovered through Trypsin-EDTA treatment, centrifuged at a speed of 1,200 rpm for 3 minutes, the supernatant was removed, resuspended in the same medium, and dispensed into 6-well plates at 1.5 mL per well to achieve the final conditions of Table 10. After treating the plate with 30 ⁇ M of compounds 50, 110, 114, and 119 or the control group (DMSO), the plate was cultured at 37°C for 48 hours in a 5% CO2 incubator.
  • MEM medium containing 10% FBS, 100 U/mL penicillin, and 100 ⁇ g/mL streptomycin.
  • control or compound-treated cells were recovered through Trypsin-EDTA treatment, fluorescent staining for Annexin V/PI (Propidium Iodide) was performed, and the results were analyzed through flow cytometry.
  • Annexin V/PI Propidium Iodide
  • the degree of apoptosis occurrence was analyzed through flow cytometry, and the sum of the ratios (%) of cells located at Annexin V High /PI High , Annexin V High /PI Low , and Annexin V Low /PI High in the data is represented as a bar graph in Figure 2.
  • Figures 1 and 2 demonstrate that the compound according to the present invention has anticancer efficacy by inducing apoptosis of cancer cells.
  • the spleen was removed from 7-week-old C57BL/6 mice, mashed, and separated into single cells using a strainer (40 ⁇ M pore size, SPL). Red blood cells were removed with ACK (Ammonium-Chloride-Potassium) lysis buffer to isolate only white blood cells. CD90.2 microbeads (130-121-278, Miltenyi Biotec.) were added, and the mixture was incubated at 4°C for 20 minutes. Then, T cells in the spleen were finally isolated using the MACS Magnetic Stand and LS column.
  • ACK Ammonium-Chloride-Potassium
  • T cells isolated from the spleen were resuspended in 1 mL of free media (RPMI-1640 + 200 U/mL penicillin + 200 ⁇ g/mL streptomycin), 0.3 ⁇ L of CFSE (10 mM) was added, and the mixture was incubated at 37°C for 5 minutes. After that, 10 mL of Free media was added to stop the reaction, and the cell pellet was obtained by centrifugation.
  • free media RPMI-1640 + 200 U/mL penicillin + 200 ⁇ g/mL streptomycin
  • T cell proliferation inhibition rate (%) is shown in Table 11.
  • Adaptive immunity exhibits a stronger immune response than innate immunity, and can be divided into immune responses mediated by T cells and immune responses mediated by B cells.
  • the compound according to the present invention exhibits a strong immunosuppressive function by inhibiting the proliferation of T cells as shown in Table 11, and inducing the death of B cells as shown in Table 2, and therefore can be usefully used for the treatment or prevention of autoimmune diseases that form autoantibodies in addition to transplant rejection.

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Abstract

La présente invention concerne un nouveau composé bicyclique et son utilisation et, en particulier, l'utilisation d'un composé de formule chimique 1 et d'un sel de celui-ci pour le traitement ou la prévention du cancer ou d'une maladie auto-immune. La présente invention concerne également une composition pour le traitement, la prévention ou le soulagement du cancer ou d'une maladie auto-immune, la composition comprenant le composé et un sel de celui-ci en tant que principe actif. La présente invention concerne également une méthode de traitement, de prévention ou de soulagement du cancer ou d'une maladie auto-immune par administration du composé et d'un sel de celui-ci à un sujet.
PCT/KR2024/001580 2023-02-01 2024-02-01 Nouveau composé bicyclique et son utilisation Ceased WO2024162814A1 (fr)

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Citations (6)

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WO1998011073A1 (fr) * 1996-09-10 1998-03-19 Pharmacia & Upjohn Company 8-hydroxyquinoleines 7-substituees utilisees comme agents antiviraux
WO1998027815A1 (fr) * 1996-12-20 1998-07-02 Merck & Co., Inc. Aminoquinoleines substituees utilisees comme modulateurs de l'activite des recepteurs de la chemokine
JPH11184040A (ja) * 1997-12-25 1999-07-09 Konica Corp ハロゲン化銀カラー写真感光材料
US5955002A (en) * 1997-11-12 1999-09-21 Spectra Group Limited, Inc. Method for determining properties of a polymer coating or film cured by cationic polymerization
WO2003050078A1 (fr) * 2001-12-13 2003-06-19 Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo Derive de naphtol et agent de controle de charge contenant ce derive
WO2023008973A1 (fr) * 2021-07-29 2023-02-02 프라비바이오 주식회사 Nouveau dérivé de benzène et son utilisation associée à l'immunosuppression

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Publication number Priority date Publication date Assignee Title
WO1998011073A1 (fr) * 1996-09-10 1998-03-19 Pharmacia & Upjohn Company 8-hydroxyquinoleines 7-substituees utilisees comme agents antiviraux
WO1998027815A1 (fr) * 1996-12-20 1998-07-02 Merck & Co., Inc. Aminoquinoleines substituees utilisees comme modulateurs de l'activite des recepteurs de la chemokine
US5955002A (en) * 1997-11-12 1999-09-21 Spectra Group Limited, Inc. Method for determining properties of a polymer coating or film cured by cationic polymerization
JPH11184040A (ja) * 1997-12-25 1999-07-09 Konica Corp ハロゲン化銀カラー写真感光材料
WO2003050078A1 (fr) * 2001-12-13 2003-06-19 Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo Derive de naphtol et agent de controle de charge contenant ce derive
WO2023008973A1 (fr) * 2021-07-29 2023-02-02 프라비바이오 주식회사 Nouveau dérivé de benzène et son utilisation associée à l'immunosuppression

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DATABASE Registry 7 June 2019 (2019-06-07), "1-Naphthaleneacetamide, N-dod ecyl-", XP093196258, Database accession no. 2325936-73-8 *

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