AR122986A1 - Derivados de piridazina como inhibidores de alk5 y/o alk4 - Google Patents
Derivados de piridazina como inhibidores de alk5 y/o alk4Info
- Publication number
- AR122986A1 AR122986A1 ARP210101996A ARP210101996A AR122986A1 AR 122986 A1 AR122986 A1 AR 122986A1 AR P210101996 A ARP210101996 A AR P210101996A AR P210101996 A ARP210101996 A AR P210101996A AR 122986 A1 AR122986 A1 AR 122986A1
- Authority
- AR
- Argentina
- Prior art keywords
- heterocycloalkyl
- alkyl
- group
- optionally substituted
- alkylene
- Prior art date
Links
- 102100034134 Activin receptor type-1B Human genes 0.000 title 1
- 101000799189 Homo sapiens Activin receptor type-1B Proteins 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical class C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 10
- 125000000592 heterocycloalkyl group Chemical group 0.000 abstract 8
- 150000001875 compounds Chemical class 0.000 abstract 5
- 241000124008 Mammalia Species 0.000 abstract 1
- 102000009618 Transforming Growth Factors Human genes 0.000 abstract 1
- 108010009583 Transforming Growth Factors Proteins 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 230000008482 dysregulation Effects 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 230000019491 signal transduction Effects 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
La presente invención se refiere a un compuesto de fórmula general (1) que inhibe el receptor del factor de crecimiento transformante b (TGF-b) de tipo I (ALK5), a métodos de preparación de dichos compuestos, a composiciones farmacéuticas que los contienen y al uso terapéutico de estos. Los compuestos de la invención pueden ser útiles en el tratamiento de enfermedades o condiciones asociadas con una desregulación de la vía de señalización de ALK5 en un mamífero. Reivindicación 1: Un compuesto de la fórmula (1) caracterizado por que R¹ es arilo opcionalmente sustituido por uno o más átomos de halógeno; A se selecciona de los grupos que consisten en los compuestos de fórmula (2), (3) y (4); R² se selecciona del grupo que consiste en -NR⁵C(O)R⁶ y -NR⁵R⁶; X¹ es C, CH o N; R³ se selecciona del grupo que consiste en -C(O)NR⁵R⁷, -C(O)OR⁷, -OC(O)R⁷, -OR⁷, -NR⁵C(O)R⁷ y -OC(O)NR⁵R⁷; R⁴ se selecciona del grupo que consiste en -C(O)NR⁵R⁷ y -C(O)heterocicloalquilo, donde dicho heterocicloalquilo está opcionalmente sustituido por uno o más -alquilo(C₁-C₆); R⁵ es H o -alquilo(C₁-C₆); R⁶ se selecciona del grupo que consiste en -alquileno(C₁-C₆)-NRARB, cicloalquilo, heterocicloalquilo sustituido por uno o más -alquilo(C₁-C₆) y -alquileno(C₁-C₆)-heterocicloalquilo, donde dicho heterocicloalquilo está opcionalmente sustituido por uno o más grupos seleccionados de -alquilo(C₁-C₆), -haloalquilo(C₁-C₆), -C(O)-alquilo(C₁-C₆), -SO₂-alquilo(C₁-C₆) y oxo; R⁷ se selecciona del grupo que consiste en lo siguiente: alquileno(C₁-C₆)-NRARB, heterocicloalquilo sustituido por uno o más -alquilo(C₁-C₆), -alquileno(C₁-C₆)-C(O)-heterocicloalquilo, donde dicho heterocicloalquilo está opcionalmente sustituido por uno o más -alquilo(C₁-C₆) y -alquileno(C₁-C₆)-heterocicloalquilo, donde dicho heterocicloalquilo está opcionalmente sustituido por uno o más grupos seleccionados de -alquilo(C₁-C₆), -haloalquilo(C₁-C₆) y -C(O)-alquilo(C₁-C₆); RA es -alquilo(C₁-C₆); RB es heterocicloalquilo; R⁸ es H o -alquilo(C₁-C₆); y sales farmacéuticamente aceptables de este.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP20185890 | 2020-07-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR122986A1 true AR122986A1 (es) | 2022-10-19 |
Family
ID=71620257
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP210101996A AR122986A1 (es) | 2020-07-15 | 2021-07-15 | Derivados de piridazina como inhibidores de alk5 y/o alk4 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US12479826B2 (es) |
| EP (1) | EP4182308B1 (es) |
| JP (1) | JP7686741B2 (es) |
| KR (1) | KR20230051500A (es) |
| CN (1) | CN116096719B (es) |
| AR (1) | AR122986A1 (es) |
| AU (1) | AU2021307559A1 (es) |
| BR (1) | BR112023000588A8 (es) |
| CA (1) | CA3184990A1 (es) |
| DK (1) | DK4182308T3 (es) |
| ES (1) | ES2997111T3 (es) |
| FI (1) | FI4182308T3 (es) |
| HR (1) | HRP20241617T1 (es) |
| HU (1) | HUE069150T2 (es) |
| MX (1) | MX2023000521A (es) |
| PL (1) | PL4182308T3 (es) |
| PT (1) | PT4182308T (es) |
| SI (1) | SI4182308T1 (es) |
| TW (1) | TW202216677A (es) |
| WO (1) | WO2022013307A1 (es) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7702205B2 (ja) * | 2021-09-15 | 2025-07-03 | 株式会社東芝 | 新規アミン化合物、酸性ガス吸収剤、酸性ガスの除去方法及び酸性ガス除去 |
| CN114957331A (zh) * | 2022-04-22 | 2022-08-30 | 北京康辰药业股份有限公司 | 磷酸酯取代的环丙酰胺衍生喹唑啉类化合物的制备方法 |
| WO2024180207A1 (en) | 2023-03-02 | 2024-09-06 | Chiesi Farmaceutici S.P.A. | Pyridazinyl amino derivatives as alk5 inhibitors |
| EP4673214A1 (en) | 2023-03-02 | 2026-01-07 | Chiesi Farmaceutici S.p.A. | Pyridazinyl amino derivatives as alk5 inhibitors |
| KR20240159754A (ko) * | 2023-04-28 | 2024-11-06 | 한국원자력의학원 | N-메틸피페라진 에탄올 카바메이트(N-methylpiperazine ethanol carbamate) 구조를 포함하는 신규 화합물 및 이의 용도 |
| WO2025132460A1 (en) | 2023-12-18 | 2025-06-26 | Chiesi Farmaceutici S.P.A. | Pyridazinyl amino derivatives as alk5 inhibitors |
| WO2025132458A1 (en) | 2023-12-18 | 2025-06-26 | Chiesi Farmaceutici S.P.A. | Pyridazinyl amino derivatives as alk5 inhibitors |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU4798000A (en) | 1999-04-09 | 2000-11-14 | Smithkline Beecham Corporation | Triarylimidazoles |
| CO5271680A1 (es) | 2000-02-21 | 2003-04-30 | Smithkline Beecham Corp | Compuestos |
| GB0007405D0 (en) | 2000-03-27 | 2000-05-17 | Smithkline Beecham Corp | Compounds |
| WO2002022607A1 (en) | 2000-09-15 | 2002-03-21 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| JP2004523474A (ja) | 2000-09-20 | 2004-08-05 | オーソ−マクニール・フアーマシユーチカル・インコーポレーテツド | チロシンキナーゼモジュレーターとしてのピラジン誘導体 |
| AR039241A1 (es) | 2002-04-04 | 2005-02-16 | Biogen Inc | Heteroarilos trisustituidos y metodos para su produccion y uso de los mismos |
| EP1549316A4 (en) * | 2002-09-10 | 2008-04-09 | Scios Inc | HAMMER OF TFGbeta |
| EP1670794A2 (en) | 2003-09-30 | 2006-06-21 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| EP2044056B1 (en) | 2006-07-14 | 2012-08-22 | Novartis AG | Pyrimidine derivatives as alk-5 inhibitors |
| BRPI0813625A2 (pt) | 2007-07-26 | 2014-12-23 | Novartis Ag | Imidazo-[1,2b]-piridozinas 2,3,7-substituídos para tratamento de doenças mediadas por alzk4 ou alk5 |
| CN101827844B (zh) | 2007-10-17 | 2013-08-14 | 诺瓦提斯公司 | 可用作ALK抑制剂的咪唑并[1,2-a]吡啶衍生物 |
| AR070127A1 (es) | 2008-01-11 | 2010-03-17 | Novartis Ag | Pirrolo - pirimidinas y pirrolo -piridinas |
| US8343966B2 (en) | 2008-01-11 | 2013-01-01 | Novartis Ag | Organic compounds |
| PT2231642E (pt) | 2008-01-11 | 2014-03-12 | Novartis Ag | Pirimidinas como inibidores de quinase |
| BRPI0911490A2 (pt) | 2008-04-29 | 2016-01-05 | Novartis Ag | derivados de imidazo-piridina como inibidores de cinase receptora tipo activina (alk4 ou alk5) |
| JP5827627B2 (ja) * | 2009-11-07 | 2015-12-02 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | ＴＧＦ−β受容体キナーゼ阻害剤としてのヘテロアリールアミノキノリン |
| MX369576B (es) | 2011-07-13 | 2019-11-13 | Tiumbio Co Ltd | Imidazoles 2-piridilo sustituidos como inhibidores de alk5 y/o alk4. |
| EP3089971B1 (en) * | 2014-01-01 | 2020-07-29 | Medivation Technologies LLC | Compounds and methods of use |
| US20200247812A1 (en) * | 2018-07-10 | 2020-08-06 | Integral Biosciences Private Limited | Heterocyclic compounds and methods of use |
-
2021
- 2021-07-14 DK DK21743186.5T patent/DK4182308T3/da active
- 2021-07-14 EP EP21743186.5A patent/EP4182308B1/en active Active
- 2021-07-14 HU HUE21743186A patent/HUE069150T2/hu unknown
- 2021-07-14 CA CA3184990A patent/CA3184990A1/en active Pending
- 2021-07-14 SI SI202130217T patent/SI4182308T1/sl unknown
- 2021-07-14 KR KR1020237005127A patent/KR20230051500A/ko active Pending
- 2021-07-14 HR HRP20241617TT patent/HRP20241617T1/hr unknown
- 2021-07-14 AU AU2021307559A patent/AU2021307559A1/en active Pending
- 2021-07-14 JP JP2023502861A patent/JP7686741B2/ja active Active
- 2021-07-14 ES ES21743186T patent/ES2997111T3/es active Active
- 2021-07-14 CN CN202180061803.6A patent/CN116096719B/zh active Active
- 2021-07-14 PT PT217431865T patent/PT4182308T/pt unknown
- 2021-07-14 US US18/014,764 patent/US12479826B2/en active Active
- 2021-07-14 FI FIEP21743186.5T patent/FI4182308T3/fi active
- 2021-07-14 WO PCT/EP2021/069649 patent/WO2022013307A1/en not_active Ceased
- 2021-07-14 MX MX2023000521A patent/MX2023000521A/es unknown
- 2021-07-14 BR BR112023000588A patent/BR112023000588A8/pt unknown
- 2021-07-14 PL PL21743186.5T patent/PL4182308T3/pl unknown
- 2021-07-15 TW TW110126103A patent/TW202216677A/zh unknown
- 2021-07-15 AR ARP210101996A patent/AR122986A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN116096719A (zh) | 2023-05-09 |
| DK4182308T3 (da) | 2024-10-21 |
| TW202216677A (zh) | 2022-05-01 |
| PT4182308T (pt) | 2024-12-04 |
| EP4182308B1 (en) | 2024-09-04 |
| JP7686741B2 (ja) | 2025-06-02 |
| CA3184990A1 (en) | 2022-01-20 |
| EP4182308A1 (en) | 2023-05-24 |
| AU2021307559A1 (en) | 2023-02-16 |
| CN116096719B (zh) | 2025-09-30 |
| MX2023000521A (es) | 2023-02-13 |
| US12479826B2 (en) | 2025-11-25 |
| HUE069150T2 (hu) | 2025-02-28 |
| JP2023533849A (ja) | 2023-08-04 |
| FI4182308T3 (fi) | 2024-12-07 |
| BR112023000588A8 (pt) | 2023-05-09 |
| HRP20241617T1 (hr) | 2025-01-31 |
| PL4182308T3 (pl) | 2025-01-07 |
| SI4182308T1 (sl) | 2025-04-30 |
| US20240018122A1 (en) | 2024-01-18 |
| WO2022013307A1 (en) | 2022-01-20 |
| ES2997111T3 (en) | 2025-03-19 |
| BR112023000588A2 (pt) | 2023-01-31 |
| KR20230051500A (ko) | 2023-04-18 |
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