MX2023014138A - Compuestos. - Google Patents
Compuestos.Info
- Publication number
- MX2023014138A MX2023014138A MX2023014138A MX2023014138A MX2023014138A MX 2023014138 A MX2023014138 A MX 2023014138A MX 2023014138 A MX2023014138 A MX 2023014138A MX 2023014138 A MX2023014138 A MX 2023014138A MX 2023014138 A MX2023014138 A MX 2023014138A
- Authority
- MX
- Mexico
- Prior art keywords
- pyrido
- mutant proteins
- compounds capable
- kras mutant
- pyrimidine compounds
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- 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
-
- 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
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with 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
- 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
- A61K31/5386—1,4-Oxazines, e.g. morpholine spiro-condensed or forming part of bridged ring systems
-
- 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
- A61K31/54—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 sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/541—Non-condensed thiazines 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/553—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one oxygen as ring hetero atoms, e.g. loxapine, staurosporine
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/554—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one sulfur as ring hetero atoms, e.g. clothiapine, diltiazem
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
- C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
-
- 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
- C07D498/08—Bridged systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB2107637.7A GB202107637D0 (en) | 2021-05-28 | 2021-05-28 | Compounds |
| GB202118635 | 2021-12-21 | ||
| PCT/GB2022/051367 WO2022248885A2 (en) | 2021-05-28 | 2022-05-27 | Compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2023014138A true MX2023014138A (es) | 2024-02-13 |
Family
ID=82019773
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2023014138A MX2023014138A (es) | 2021-05-28 | 2022-05-27 | Compuestos. |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20240279241A1 (https=) |
| EP (1) | EP4347589A2 (https=) |
| JP (1) | JP2024519170A (https=) |
| KR (1) | KR20240013776A (https=) |
| AU (1) | AU2022279653A1 (https=) |
| BR (1) | BR112023024906A2 (https=) |
| CA (1) | CA3216294A1 (https=) |
| IL (1) | IL308438A (https=) |
| MX (1) | MX2023014138A (https=) |
| WO (1) | WO2022248885A2 (https=) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US12479834B2 (en) | 2019-11-29 | 2025-11-25 | Taiho Pharmaceutical Co., Ltd. | Phenol compound or salt thereof |
| EP4161926A4 (en) * | 2020-06-03 | 2024-06-19 | Yumanity Therapeutics, Inc. | PYRIDOPYRIMIDINES AND THEIR METHODS OF USE |
| WO2023018812A1 (en) * | 2021-08-10 | 2023-02-16 | Amgen Inc. | Heterocyclic compounds and methods of use |
| TW202328124A (zh) * | 2021-08-18 | 2023-07-16 | 大陸商北京加科思新藥研發有限公司 | 1,4-氧雜氮雜環庚烷衍生物及其用途 |
| WO2023061294A1 (zh) * | 2021-10-13 | 2023-04-20 | 再鼎医药(上海)有限公司 | 含氮杂环类衍生物调节剂、其制备方法及应用 |
| TW202334138A (zh) | 2021-11-05 | 2023-09-01 | 美商新領域醫藥公司 | 癌症治療方法 |
| JP2024543879A (ja) * | 2021-11-24 | 2024-11-26 | メルク・シャープ・アンド・ドーム・エルエルシー | Kras変異型タンパク質の小分子阻害剤 |
| EP4444289A4 (en) * | 2021-12-08 | 2025-12-17 | Kineta Inc | PYRIDOPYRIMIDINS AND METHODS FOR THEIR USE |
| CN118556063A (zh) * | 2022-01-21 | 2024-08-27 | 上海湃隆生物科技有限公司 | 杂环类化合物、药物组合物及其应用 |
| CN118900838A (zh) * | 2022-03-24 | 2024-11-05 | 百济神州有限公司 | 杂环化合物、其组合物及其治疗方法 |
| WO2023213269A1 (en) * | 2022-05-06 | 2023-11-09 | Zai Lab (Shanghai) Co., Ltd. | Amide-substituted heterocyclic compounds as kras g12d modulators and uses thereof |
| WO2023246777A1 (en) * | 2022-06-20 | 2023-12-28 | Jacobio Pharmaceuticals Co., Ltd. | K-ras mutant protein inhibitors |
| WO2024008068A1 (en) * | 2022-07-04 | 2024-01-11 | Jacobio Pharmaceuticals Co., Ltd. | K-ras mutant protein inhibitors |
| WO2024012519A1 (zh) * | 2022-07-13 | 2024-01-18 | 北京华森英诺生物科技有限公司 | Pan-kras抑制剂 |
| CN117624170A (zh) * | 2022-08-24 | 2024-03-01 | 泰励生物科技(上海)有限公司 | 具有抗kras突变肿瘤活性的化合物 |
| CN120077051A (zh) * | 2022-10-21 | 2025-05-30 | 苏州亚盛药业有限公司 | Kras抑制剂 |
| WO2024112654A1 (en) | 2022-11-21 | 2024-05-30 | Treeline Biosciences, Inc. | Spirocyclic dihydropyranopyrimidine kras inhibitors |
| CN118165011A (zh) * | 2022-12-08 | 2024-06-11 | 润佳(上海)医药工程有限公司 | Kras抑制剂及其用途 |
| WO2024125600A1 (zh) * | 2022-12-14 | 2024-06-20 | 上海科州药物研发有限公司 | 作为kras抑制剂的杂环化合物,及其制备和治疗用途 |
| WO2024138206A1 (en) * | 2022-12-23 | 2024-06-27 | Frontier Medicines Corporation | Fluoropyridopyrimidine and fluoroquinazoline derivaties and methods of use thereof |
| WO2024209339A1 (en) * | 2023-04-05 | 2024-10-10 | Pfizer Inc. | Pyrido[4,3-d]pyrimidine compounds |
| KR20260015208A (ko) | 2023-05-12 | 2026-02-02 | 재즈 파마슈티칼즈 아일랜드 리미티드 | 암 치료에 유용한 g12d 돌연변이체 kras의 조절제로서 피라졸로[4,3-f]퀴나졸린 유도체 |
| CN119101070A (zh) * | 2023-06-07 | 2024-12-10 | 上海璎黎药业有限公司 | 一种含氮杂环化合物、其药物组合物及应用 |
| IL326136A (en) | 2023-08-07 | 2026-03-01 | Revolution Medicines Inc | RMC-6291 for use in the treatment of a disease or disorder associated with the RAS protein |
| AU2024323424A1 (en) | 2023-08-17 | 2026-03-05 | Treeline Biosciences, Inc. | Spirocyclic dihydropyranopyrimidine kras inhibitors |
| AU2024337913A1 (en) | 2023-09-08 | 2026-03-26 | Gilead Sciences, Inc. | Pyrimidine-containing polycyclic derivatives as kras g12d modulating compounds |
| TW202528315A (zh) | 2023-09-21 | 2025-07-16 | 美商樹線生物科學公司 | 螺環二氫哌喃并吡啶KRas抑制劑 |
| US20250154171A1 (en) | 2023-10-12 | 2025-05-15 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2025085748A1 (en) | 2023-10-20 | 2025-04-24 | Merck Sharp & Dohme Llc | Small molecule inhibitors of kras proteins |
| WO2025163494A1 (en) | 2024-01-29 | 2025-08-07 | Jazz Pharmaceuticals Ireland Ltd. | Condensed azines for the treatment of cancer |
| WO2025171296A1 (en) | 2024-02-09 | 2025-08-14 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2025235740A1 (en) * | 2024-05-08 | 2025-11-13 | Merck Sharp & Dohme Llc | Small molecule inhibitors of kras proteins |
| WO2025240847A1 (en) | 2024-05-17 | 2025-11-20 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2025245127A1 (en) | 2024-05-21 | 2025-11-27 | Treeline Biosciences, Inc. | Spirocyclic dihydropyranopyrimidine kras inhibitors |
| US20250375445A1 (en) | 2024-06-07 | 2025-12-11 | Revolution Medicines, Inc. | Methods of treating a ras protein-related disease or disorder |
| WO2025265060A1 (en) | 2024-06-21 | 2025-12-26 | Revolution Medicines, Inc. | Therapeutic compositions and methods for managing treatment-related effects |
| WO2026006747A1 (en) | 2024-06-28 | 2026-01-02 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2026015796A1 (en) | 2024-07-12 | 2026-01-15 | Revolution Medicines, Inc. | Methods of treating a ras related disease or disorder |
| WO2026015825A1 (en) | 2024-07-12 | 2026-01-15 | Revolution Medicines, Inc. | Use of ras inhibitor for treating pancreatic cancer |
| WO2026015790A1 (en) | 2024-07-12 | 2026-01-15 | Revolution Medicines, Inc. | Methods of treating a ras related disease or disorder |
| WO2026015801A1 (en) | 2024-07-12 | 2026-01-15 | Revolution Medicines, Inc. | Methods of treating a ras related disease or disorder |
| WO2026050446A1 (en) | 2024-08-29 | 2026-03-05 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2026072904A2 (en) | 2024-09-26 | 2026-04-02 | Revolution Medicines, Inc. | Compositions and methods for treating lung cancer |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201942115A (zh) * | 2018-02-01 | 2019-11-01 | 美商輝瑞股份有限公司 | 作為抗癌藥之經取代的喹唑啉和吡啶並嘧啶衍生物 |
| WO2020146613A1 (en) * | 2019-01-10 | 2020-07-16 | Mirati Therapeutics, Inc. | Kras g12c inhibitors |
| WO2021041671A1 (en) | 2019-08-29 | 2021-03-04 | Mirati Therapeutics, Inc. | Kras g12d inhibitors |
| EP4192585A4 (en) * | 2020-08-04 | 2024-08-21 | Mirati Therapeutics, Inc. | Kras g12d inhibitors |
| CN115968286A (zh) * | 2020-08-26 | 2023-04-14 | 益方生物科技(上海)股份有限公司 | 杂芳基化合物,其制备方法和用途 |
| US20230081426A1 (en) * | 2020-09-18 | 2023-03-16 | Plexxikon Inc. | Compounds and methods for kras modulation and indications therefor |
| US20230365563A1 (en) * | 2020-09-30 | 2023-11-16 | Shanghai Pharmaceuticals Holding Co., Ltd. | Quinazoline compound and application thereof |
| WO2022098625A1 (en) * | 2020-11-03 | 2022-05-12 | Mirati Therapeutics, Inc. | Kras g12d inhibitors |
| WO2022132200A1 (en) * | 2020-12-15 | 2022-06-23 | Mirati Therapeutics, Inc. | Azaquinazoline pan-kras inhibitors |
| CN113999226B (zh) * | 2020-12-22 | 2023-01-06 | 上海科州药物研发有限公司 | 作为kras抑制剂的杂环化合物的制备及其应用方法 |
| WO2022256459A1 (en) * | 2021-06-01 | 2022-12-08 | Quanta Therapeutics, Inc. | Kras modulators and uses thereof |
-
2022
- 2022-05-27 WO PCT/GB2022/051367 patent/WO2022248885A2/en not_active Ceased
- 2022-05-27 KR KR1020237044372A patent/KR20240013776A/ko active Pending
- 2022-05-27 AU AU2022279653A patent/AU2022279653A1/en active Pending
- 2022-05-27 JP JP2023573109A patent/JP2024519170A/ja active Pending
- 2022-05-27 MX MX2023014138A patent/MX2023014138A/es unknown
- 2022-05-27 CA CA3216294A patent/CA3216294A1/en active Pending
- 2022-05-27 US US18/562,608 patent/US20240279241A1/en active Pending
- 2022-05-27 BR BR112023024906A patent/BR112023024906A2/pt unknown
- 2022-05-27 EP EP22729759.5A patent/EP4347589A2/en active Pending
- 2022-05-27 IL IL308438A patent/IL308438A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2024519170A (ja) | 2024-05-08 |
| KR20240013776A (ko) | 2024-01-30 |
| AU2022279653A1 (en) | 2023-11-09 |
| IL308438A (en) | 2024-01-01 |
| CA3216294A1 (en) | 2022-12-01 |
| BR112023024906A2 (pt) | 2024-02-15 |
| WO2022248885A2 (en) | 2022-12-01 |
| US20240279241A1 (en) | 2024-08-22 |
| EP4347589A2 (en) | 2024-04-10 |
| WO2022248885A3 (en) | 2023-02-16 |
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