JP7836762B2 - ヘテロ環glp-1アゴニスト - Google Patents
ヘテロ環glp-1アゴニストInfo
- Publication number
- JP7836762B2 JP7836762B2 JP2022549132A JP2022549132A JP7836762B2 JP 7836762 B2 JP7836762 B2 JP 7836762B2 JP 2022549132 A JP2022549132 A JP 2022549132A JP 2022549132 A JP2022549132 A JP 2022549132A JP 7836762 B2 JP7836762 B2 JP 7836762B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- pharmaceutically acceptable
- ring
- solvate
- acceptable salt
- 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.)
- Active
Links
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
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
-
- 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
- A61K31/13—Amines
- A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/423—Oxazoles condensed with carbocyclic 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
- A61K31/4965—Non-condensed pyrazines
- A61K31/497—Non-condensed pyrazines 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
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/1703—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates
- A61K38/1709—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates from mammals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/22—Hormones
- A61K38/26—Glucagons
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/22—Hormones
- A61K38/28—Insulins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K39/395—Antibodies; Immunoglobulins; Immune serum, e.g. antilymphocytic serum
- A61K39/39533—Antibodies; Immunoglobulins; Immune serum, e.g. antilymphocytic serum against materials from animals
- A61K39/3955—Antibodies; Immunoglobulins; Immune serum, e.g. antilymphocytic serum against materials from animals against proteinaceous materials, e.g. enzymes, hormones, lymphokines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Immunology (AREA)
- Endocrinology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Gastroenterology & Hepatology (AREA)
- Zoology (AREA)
- Emergency Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Obesity (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Hematology (AREA)
- Microbiology (AREA)
- Marine Sciences & Fisheries (AREA)
- Mycology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNPCT/CN2020/075105 | 2020-02-13 | ||
| CN2020075103 | 2020-02-13 | ||
| CN2020075105 | 2020-02-13 | ||
| CNPCT/CN2020/075103 | 2020-02-13 | ||
| PCT/CN2021/076260 WO2021160127A1 (en) | 2020-02-13 | 2021-02-09 | Heterocyclic glp-1 agonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2023515404A JP2023515404A (ja) | 2023-04-13 |
| JP2023515404A5 JP2023515404A5 (https=) | 2024-02-20 |
| JP7836762B2 true JP7836762B2 (ja) | 2026-03-27 |
Family
ID=77291666
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022549132A Active JP7836762B2 (ja) | 2020-02-13 | 2021-02-09 | ヘテロ環glp-1アゴニスト |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20230165846A1 (https=) |
| EP (1) | EP4103563A4 (https=) |
| JP (1) | JP7836762B2 (https=) |
| CN (1) | CN115697999A (https=) |
| WO (1) | WO2021160127A1 (https=) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MA54555A (fr) | 2018-11-22 | 2021-09-29 | Qilu Regor Therapeutics Inc | Agonistes de glp-1r et leurs utilisations |
| EP3953344A4 (en) | 2019-04-12 | 2023-08-09 | Qilu Regor Therapeutics Inc. | GLP-IR AGONISTS AND THEIR USES |
| TWI751585B (zh) | 2019-06-28 | 2022-01-01 | 美商美國禮來大藥廠 | 類升糖素肽1受體促效劑 |
| EP4048664A1 (en) | 2019-10-25 | 2022-08-31 | Gilead Sciences, Inc. | Glp-1r modulating compounds |
| CN114761395B (zh) * | 2019-12-02 | 2024-11-15 | 现代药品株式会社 | Glp-1受体激动剂 |
| ES3016132T3 (en) | 2020-01-29 | 2025-05-08 | Gilead Sciences Inc | Glp-1r modulating compounds |
| HRP20241159T1 (hr) | 2020-02-07 | 2024-12-06 | Gasherbrum Bio, Inc. | Heterociklički agonisti za glp-1 |
| IL296336A (en) * | 2020-03-18 | 2022-11-01 | Lg Chemical Ltd | Glp-1 receptor agonist, pharmaceutical composition comprising same, and method for preparing same |
| TW202144340A (zh) * | 2020-04-03 | 2021-12-01 | 大陸商江蘇恆瑞醫藥股份有限公司 | 稠合咪唑類衍生物、其製備方法及其在醫藥上的應用 |
| TW202206429A (zh) | 2020-04-29 | 2022-02-16 | 美商迦舒布魯姆生物有限公司 | 雜環glp—1促效劑 |
| JP2023537501A (ja) | 2020-08-06 | 2023-09-01 | ガシャーブラム・バイオ・インコーポレイテッド | ヘテロ環glp-1アゴニスト |
| EP4204415A4 (en) | 2020-08-28 | 2025-03-26 | Gasherbrum Bio, Inc. | HETEROCYCLIC GLP-1 AGONISTS |
| CN116368140A (zh) | 2020-09-10 | 2023-06-30 | 加舒布鲁姆生物公司 | 杂环glp-1激动剂 |
| EP4247804A1 (en) | 2020-11-20 | 2023-09-27 | Gilead Sciences, Inc. | Polyheterocyclic glp-1 r modulating compounds |
| MX2023006186A (es) * | 2020-11-27 | 2023-08-07 | Shenzhen Salubris Pharm Co Ltd | Derivado de benzimidazol y método de preparación del mismo y uso médico del mismo. |
| WO2022192428A1 (en) | 2021-03-11 | 2022-09-15 | Gilead Sciences, Inc. | Glp-1r modulating compounds |
| EP4304712A1 (en) | 2021-03-11 | 2024-01-17 | Gilead Sciences, Inc. | Glp-1r modulating compounds |
| JP7772778B2 (ja) | 2021-03-24 | 2025-11-18 | 塩野義製薬株式会社 | 縮合環を有するglp-1受容体作動薬を含有する医薬組成物 |
| WO2022216094A1 (ko) * | 2021-04-08 | 2022-10-13 | 주식회사 엘지화학 | Glp-1 수용체 효능제, 이를 포함하는 약학적 조성물 및 이의 제조방법 |
| IL306110A (en) | 2021-04-21 | 2023-11-01 | Gilead Sciences Inc | Carboxy-benzimidazole glp-1r modulating compounds |
| TWI843104B (zh) | 2021-05-20 | 2024-05-21 | 美商美國禮來大藥廠 | 類升糖素肽1受體促效劑 |
| IL309235A (en) * | 2021-06-24 | 2024-02-01 | Hangzhou Zhongmeihuadong Pharmaceutical Co Ltd | Glp-1 receptor agonist and composition and use thereof |
| CN113480534B (zh) * | 2021-07-23 | 2022-05-13 | 广州必贝特医药股份有限公司 | 苯并咪唑或氮杂苯并咪唑-6-羧酸类化合物及其应用 |
| WO2023029380A1 (zh) | 2021-08-30 | 2023-03-09 | 杭州德睿智药科技有限公司 | 作为glp1r激动剂的新型芳醚取代杂环类化合物 |
| US20240374587A1 (en) | 2021-09-08 | 2024-11-14 | Shionogi & Co., Ltd. | Medicine for prevention and treatment of diseases linked to anti-obesity activity |
| PT4408840T (pt) | 2021-09-27 | 2025-10-07 | Terns Pharmaceuticals Inc | Ácidos benzimidazolocarboxílicos como agonistas de glp-1r |
| WO2023057414A1 (en) | 2021-10-05 | 2023-04-13 | Astrazeneca Ab | Certain octahydrofuro[3,4- b]pyrazines as glp-1 receptor modulators |
| US20250115612A1 (en) | 2021-10-05 | 2025-04-10 | Astrazeneca Ab | Certain 2,5-diazabicyclo[4.2.0]octanes and octahydrofuro[3,4-b]pyrazines as glp-1 receptor modulators |
| MX2024004131A (es) | 2021-10-05 | 2024-04-22 | Astrazeneca Ab | Ciertos 2,5-diazabiciclo[4.2.0]octanos como moduladores del receptor de glp-1. |
| CN118401519A (zh) | 2021-10-25 | 2024-07-26 | 拓臻制药公司 | 作为glp-1r激动剂的化合物 |
| WO2023111144A1 (en) | 2021-12-16 | 2023-06-22 | Astrazeneca Ab | Certain 3-azabicyclo[3.1.0]hexanes as glp-1 receptor modulators |
| US20250042882A1 (en) | 2021-12-16 | 2025-02-06 | Astrazeneca Ab | Certain 3-azabicyclo[3.1.0]hexanes as glp-1 receptor modulators |
| CN119095843A (zh) | 2022-02-23 | 2024-12-06 | 拓臻制药公司 | 作为glp-1r激动剂的化合物 |
| US20250136584A1 (en) * | 2022-05-20 | 2025-05-01 | Chengdu Di'ao Jiuhong Pharmaceutical Factory | Benzimidazole Or Azabenzimidazole Compound, Preparation Method Therefor And Use Thereof |
| EP4562006A1 (en) * | 2022-07-27 | 2025-06-04 | Carmot Therapeutics, Inc. | N-heterocylic gpcr receptor agonists, pharmaceutical compositions comprising the same, and methods for their use |
| EP4592285A1 (en) | 2022-09-22 | 2025-07-30 | Shionogi & Co., Ltd. | Fused ring compound having glp-1 receptor agonist effect |
| WO2024102625A1 (en) | 2022-11-11 | 2024-05-16 | Eli Lilly And Company | Glucagon-like peptide 1 receptor agonists |
| KR20250085816A (ko) | 2022-11-16 | 2025-06-12 | 일라이 릴리 앤드 캄파니 | 글루카곤-유사 펩티드 1 수용체 효능제 |
| WO2024125442A1 (zh) * | 2022-12-13 | 2024-06-20 | 杭州中美华东制药有限公司 | Glp-1受体激动剂的新晶型和制备方法及其药物组合物和用途 |
| CN120957993A (zh) | 2023-02-16 | 2025-11-14 | 加舒布鲁姆生物公司 | 杂环glp-1激动剂 |
| EP4568664B1 (en) | 2023-04-07 | 2026-04-01 | Terns Pharmaceuticals, Inc. | Combination comprising a thr-beta agonist and a glp-1r agonist for use in treating obesity |
| CN120981457A (zh) | 2023-09-14 | 2025-11-18 | 歌礼制药(中国)有限公司 | Glp-1r激动剂及其治疗方法 |
| US20250157580A1 (en) * | 2023-11-13 | 2025-05-15 | Aspen Neuroscience, Inc. | Methods of predicting dopamine production capability of differentiated neuronal cells |
| TW202521534A (zh) | 2023-11-24 | 2025-06-01 | 香港商歌禮製藥(中國)有限公司 | Glp-1r 激動劑及其治療方法 |
| WO2025158275A1 (en) | 2024-01-24 | 2025-07-31 | Pfizer Inc. | Combination therapy using glucose-dependent insulinotropic polypeptide receptor antagonist compounds and glp-1 receptor agonist compounds |
| TW202600132A (zh) | 2024-03-08 | 2026-01-01 | 美商安尼波那生物公司 | 用於治療肥胖症及提高減重之方法 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2020511411A (ja) | 2016-12-16 | 2020-04-16 | ファイザー・インク | Glp−1受容体アゴニストおよびその使用 |
| JP2021528394A (ja) | 2018-06-15 | 2021-10-21 | ファイザー・インク | Glp−1受容体アゴニストおよびその使用 |
| JP2022508203A (ja) | 2018-11-22 | 2022-01-19 | キル・レガー・セラピューティクス・インコーポレーテッド | Glp-1rアゴニスト及びその使用 |
| JP2022527607A (ja) | 2019-04-12 | 2022-06-02 | キル・レガー・セラピューティクス・インコーポレーテッド | Glp-1rアゴニスト及びその使用 |
| JP2022540044A (ja) | 2019-06-28 | 2022-09-14 | イーライ リリー アンド カンパニー | グルカゴン様ペプチド1受容体アゴニスト |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021018023A1 (zh) * | 2019-08-01 | 2021-02-04 | 济南泰达领创医药技术有限公司 | 小分子glp-1受体调节剂 |
| EP4048664A1 (en) * | 2019-10-25 | 2022-08-31 | Gilead Sciences, Inc. | Glp-1r modulating compounds |
| CN114761395B (zh) * | 2019-12-02 | 2024-11-15 | 现代药品株式会社 | Glp-1受体激动剂 |
-
2021
- 2021-02-09 JP JP2022549132A patent/JP7836762B2/ja active Active
- 2021-02-09 WO PCT/CN2021/076260 patent/WO2021160127A1/en not_active Ceased
- 2021-02-09 US US17/799,609 patent/US20230165846A1/en active Pending
- 2021-02-09 CN CN202180026644.6A patent/CN115697999A/zh active Pending
- 2021-02-09 EP EP21753402.3A patent/EP4103563A4/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2020511411A (ja) | 2016-12-16 | 2020-04-16 | ファイザー・インク | Glp−1受容体アゴニストおよびその使用 |
| JP2021528394A (ja) | 2018-06-15 | 2021-10-21 | ファイザー・インク | Glp−1受容体アゴニストおよびその使用 |
| JP2022508203A (ja) | 2018-11-22 | 2022-01-19 | キル・レガー・セラピューティクス・インコーポレーテッド | Glp-1rアゴニスト及びその使用 |
| JP2022527607A (ja) | 2019-04-12 | 2022-06-02 | キル・レガー・セラピューティクス・インコーポレーテッド | Glp-1rアゴニスト及びその使用 |
| JP2022540044A (ja) | 2019-06-28 | 2022-09-14 | イーライ リリー アンド カンパニー | グルカゴン様ペプチド1受容体アゴニスト |
Also Published As
| Publication number | Publication date |
|---|---|
| EP4103563A4 (en) | 2024-03-06 |
| JP2023515404A (ja) | 2023-04-13 |
| US20230165846A1 (en) | 2023-06-01 |
| EP4103563A1 (en) | 2022-12-21 |
| WO2021160127A1 (en) | 2021-08-19 |
| CN115697999A (zh) | 2023-02-03 |
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