ECSP099781A - Novedosos compuestos que son inhibidores de erk - Google Patents
Novedosos compuestos que son inhibidores de erkInfo
- Publication number
- ECSP099781A ECSP099781A EC2009009781A ECSP099781A ECSP099781A EC SP099781 A ECSP099781 A EC SP099781A EC 2009009781 A EC2009009781 A EC 2009009781A EC SP099781 A ECSP099781 A EC SP099781A EC SP099781 A ECSP099781 A EC SP099781A
- Authority
- EC
- Ecuador
- Prior art keywords
- erk inhibitors
- ring
- new compounds
- formula
- piperidine
- Prior art date
Links
- 239000012824 ERK inhibitor Substances 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 title abstract 2
- 125000003386 piperidinyl group Chemical group 0.000 abstract 2
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- 201000011510 cancer Diseases 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000004193 piperazinyl group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000012453 solvate Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 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
- C07D401/14—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
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- 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
- C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
Se describen los inhibidores de ERK de fórmula 1.0: y sus sales, ésteres y solvatos aceptables desde el punto de vista farmacéutico. Q es un anillo de piperidina o piperazina que pueden tener un puente o anillo fusionado. El anillo de piperidina puede tener un enlace doble en el anillo. Todos los demás sustituyentes son como se los define aquí. También se describen métodos de tratamiento para el cáncer usando los compuestos de fórmula 1.0.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/810,282 US8546404B2 (en) | 2005-12-13 | 2007-06-05 | Compounds that are ERK inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ECSP099781A true ECSP099781A (es) | 2010-01-29 |
Family
ID=39737670
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EC2009009781A ECSP099781A (es) | 2007-06-05 | 2009-12-03 | Novedosos compuestos que son inhibidores de erk |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP2155722B1 (es) |
| JP (1) | JP2010529122A (es) |
| KR (1) | KR20100025553A (es) |
| CN (1) | CN101815711A (es) |
| AR (1) | AR068046A1 (es) |
| AU (1) | AU2008262412A1 (es) |
| BR (1) | BRPI0812450A2 (es) |
| CA (1) | CA2694860A1 (es) |
| CL (1) | CL2008001633A1 (es) |
| CO (1) | CO6251261A2 (es) |
| EC (1) | ECSP099781A (es) |
| IL (1) | IL202317A0 (es) |
| MX (1) | MX2009013333A (es) |
| MY (1) | MY148609A (es) |
| NZ (1) | NZ581698A (es) |
| PE (1) | PE20090326A1 (es) |
| RU (1) | RU2475484C2 (es) |
| TW (1) | TW200911262A (es) |
| WO (1) | WO2008153858A1 (es) |
| ZA (1) | ZA200908477B (es) |
Families Citing this family (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8546404B2 (en) | 2005-12-13 | 2013-10-01 | Merck Sharp & Dohme | Compounds that are ERK inhibitors |
| CN102015693B (zh) * | 2008-02-21 | 2014-10-29 | 默沙东公司 | 作为erk抑制剂的化合物 |
| US20110278332A1 (en) * | 2009-03-26 | 2011-11-17 | Protexer, Inc. | Shoe cover removal apparatus |
| US9229008B2 (en) | 2008-08-19 | 2016-01-05 | Merck Sharp & Dohme Corp. | IL-8 level as a determinant of responsivity of a cancer to treatment |
| EP2316031B1 (en) * | 2008-08-19 | 2016-09-14 | Merck Sharp & Dohme Corp. | IL-8 biomarker for monitoring cancer treatment |
| JO2860B1 (en) | 2009-05-07 | 2015-03-15 | ايلي ليلي اند كومباني | Phenylendazolyl compounds |
| EP2584903B1 (en) | 2010-06-24 | 2018-10-24 | Merck Sharp & Dohme Corp. | Novel heterocyclic compounds as erk inhibitors |
| EP2613782B1 (en) * | 2010-09-01 | 2016-11-02 | Merck Sharp & Dohme Corp. | Indazole derivatives useful as erk inhibitors |
| WO2012087772A1 (en) | 2010-12-21 | 2012-06-28 | Schering Corporation | Indazole derivatives useful as erk inhibitors |
| EP2487159A1 (en) | 2011-02-11 | 2012-08-15 | MSD Oss B.V. | RorgammaT inhibitors |
| WO2013169858A1 (en) | 2012-05-08 | 2013-11-14 | The Broad Institute, Inc. | Diagnostic and treatment methods in patients having or at risk of developing resistance to cancer therapy |
| CN103450163B (zh) * | 2012-05-29 | 2017-06-23 | 中国医学科学院药物研究所 | 吲唑类化合物、其制备方法及其药物用途 |
| WO2014026329A1 (en) | 2012-08-15 | 2014-02-20 | Merck Sharp & Dohme Corp. | N-alkylated indole and indazole compounds as rorgammat inhibitors and uses thereof |
| WO2014026327A1 (en) | 2012-08-15 | 2014-02-20 | Merck Sharp & Dohme Corp. | 4-heteroaryl substituted benzoic acid compounds as rorgammat inhibitors and uses thereof |
| CA2882410A1 (en) | 2012-09-19 | 2014-03-27 | Novartis Ag | Dihydropyrrolidino-pyrimidines as kinase inhibitors |
| SI3052096T1 (en) | 2013-10-03 | 2018-04-30 | Kura Oncology, Inc. | EAQ inhibitors and application procedures |
| DK3063143T3 (en) | 2013-11-01 | 2018-08-20 | Novartis Ag | Amino heteroaryl benzamides as kinase inhibitors |
| BR112016014481B1 (pt) * | 2013-12-20 | 2022-11-08 | Biomed Valley Discoveries, Inc | Uso de uma composição farmacêutica, método in vitro para efetuar a morte de células cancerosas, e kit |
| AU2014368925A1 (en) * | 2013-12-20 | 2016-07-21 | Biomed Valley Discoveries, Inc. | Cancer treatments using combinations of MEK type I and ERK inhibitors |
| US11013743B2 (en) * | 2013-12-20 | 2021-05-25 | Biomed Valley Discoveries, Inc. | Cancer treatments using combinations of CDK and ERK inhibitors |
| AU2014368912B2 (en) * | 2013-12-20 | 2020-04-30 | Biomed Valley Discoveries, Inc. | Cancer treatments using combinations of type 2 MEK and ERK inhibitors |
| WO2016095088A1 (en) | 2014-12-15 | 2016-06-23 | Merck Sharp & Dohme Corp. | Erk inhibitors |
| WO2016095089A1 (en) | 2014-12-15 | 2016-06-23 | Merck Sharp & Dohme Corp. | Erk inhibitors |
| CA2975997A1 (en) | 2015-02-11 | 2016-08-18 | Merck Sharp & Dohme Corp. | Substituted pyrazole compounds as rorgammat inhibitors and uses thereof |
| GB201511382D0 (en) | 2015-06-29 | 2015-08-12 | Imp Innovations Ltd | Novel compounds and their use in therapy |
| JP2018531958A (ja) | 2015-10-27 | 2018-11-01 | メルク・シャープ・アンド・ドーム・コーポレーションＭｅｒｃｋ Ｓｈａｒｐ ＆ Ｄｏｈｍｅ Ｃｏｒｐ． | ＲＯＲγＴ阻害薬としてのヘテロアリール置換安息香酸及びその使用 |
| EP3368516B1 (en) | 2015-10-27 | 2020-07-15 | Merck Sharp & Dohme Corp. | SUBSTITUTED BICYCLIC PYRAZOLE COMPOUNDS AS RORgammaT INHIBITORS AND USES THEREOF |
| US10287272B2 (en) | 2015-10-27 | 2019-05-14 | Merck Sharp & Dohme Corp. | Substituted indazole compounds as RORgammaT inhibitors and uses thereof |
| TW201940483A (zh) | 2018-03-12 | 2019-10-16 | 美商艾伯維有限公司 | 酪胺酸激酶２介導的傳訊之抑制劑 |
| EP3725777A1 (en) * | 2019-04-17 | 2020-10-21 | Rottapharm Biotech S.r.l. | Benzo- and pyrido-pyrazoles as protein kinase inhibitors |
| CN114605329B (zh) * | 2022-03-28 | 2024-01-26 | 河南中医药大学 | 取代的吲唑甲酰胺或取代的氮杂吲唑甲酰胺类flt3抑制剂及其用途 |
| CN119997982A (zh) | 2022-09-09 | 2025-05-13 | 迈里克斯制药有限公司 | 包含nmt抑制剂的抗体药物偶联物及其用途 |
| KR20260019479A (ko) | 2023-05-04 | 2026-02-10 | 레볼루션 메디슨즈, 인크. | Ras 관련 질환 또는 장애를 위한 병용 요법 |
| CN121889155A (zh) | 2023-08-07 | 2026-04-17 | 锐新医药公司 | 用于治疗ras蛋白相关疾病或病症的rmc-6291 |
| AU2024360465A1 (en) | 2023-10-12 | 2026-04-09 | Revolution Medicines, Inc. | Macrocyclic ras inhibitors |
| WO2025171296A1 (en) | 2024-02-09 | 2025-08-14 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2025240847A1 (en) | 2024-05-17 | 2025-11-20 | Revolution Medicines, Inc. | Ras 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 |
| 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 |
| WO2026015825A1 (en) | 2024-07-12 | 2026-01-15 | Revolution Medicines, Inc. | Use of ras inhibitor for treating pancreatic cancer |
| WO2026015796A1 (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 |
| WO2026090116A2 (en) | 2024-10-21 | 2026-04-30 | Revolution Medicines, Inc. | Ras inhibitors |
| US20260108528A1 (en) | 2024-10-22 | 2026-04-23 | Revolution Medicines, Inc. | Methods of treating a ras protein-related disease or disorder |
| WO2026090245A1 (en) | 2024-10-22 | 2026-04-30 | Revolution Medicines, Inc. | Use of ras inhibitors for treating cancer |
| WO2026106912A1 (en) | 2024-11-12 | 2026-05-21 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2026112260A1 (en) | 2024-11-21 | 2026-05-28 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2026122764A2 (en) | 2024-12-06 | 2026-06-11 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2026128688A2 (en) | 2024-12-13 | 2026-06-18 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2026161839A1 (en) | 2025-01-27 | 2026-07-30 | Revolution Medicines, Inc. | Ras inhibitors |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9213077D0 (en) | 1992-06-19 | 1992-08-05 | Erba Carlo Spa | Polymerbound taxol derivatives |
| TW349948B (en) | 1995-10-31 | 1999-01-11 | Janssen Pharmaceutica Nv | Farnesyl transferase inhibiting 2-quinolone derivatives |
| US5874442A (en) | 1995-12-22 | 1999-02-23 | Schering-Plough Corporation | Tricyclic amides useful for inhibition of G-protein function and for treatment of proliferative disease |
| US6011029A (en) | 1996-02-26 | 2000-01-04 | Bristol-Myers Squibb Company | Inhibitors of farnesyl protein transferase |
| US6632455B2 (en) | 1997-12-22 | 2003-10-14 | Schering Corporation | Molecular dispersion composition with enhanced bioavailability |
| US6130235A (en) * | 1998-05-22 | 2000-10-10 | Scios Inc. | Compounds and methods to treat cardiac failure and other disorders |
| MY130778A (en) * | 2001-02-09 | 2007-07-31 | Vertex Pharma | Heterocyclic inhibitiors of erk2 and uses thereof |
| JP2004538266A (ja) * | 2001-04-27 | 2004-12-24 | バーテックス ファーマシューティカルズ インコーポレイテッド | ピラゾール由来のキナーゼインヒビター |
| ES2897422T3 (es) * | 2004-05-14 | 2022-03-01 | Vertex Pharma | Compuestos pirroles como inhibidores de proteínas cinasas ERK y composiciones farmacéuticas que contienen esos compuestos |
| ES2372976T3 (es) * | 2005-12-13 | 2012-01-30 | Schering Corporation | Derivados de indazol policíclicos que son inhibidores de erk. |
-
2008
- 2008-06-04 AR ARP080102366A patent/AR068046A1/es unknown
- 2008-06-04 JP JP2010511172A patent/JP2010529122A/ja not_active Ceased
- 2008-06-04 TW TW097120755A patent/TW200911262A/zh unknown
- 2008-06-04 BR BRPI0812450A patent/BRPI0812450A2/pt not_active IP Right Cessation
- 2008-06-04 AU AU2008262412A patent/AU2008262412A1/en not_active Abandoned
- 2008-06-04 EP EP08768067.4A patent/EP2155722B1/en active Active
- 2008-06-04 CN CN200880100968A patent/CN101815711A/zh active Pending
- 2008-06-04 NZ NZ581698A patent/NZ581698A/xx not_active IP Right Cessation
- 2008-06-04 PE PE2008000942A patent/PE20090326A1/es not_active Application Discontinuation
- 2008-06-04 KR KR1020097027487A patent/KR20100025553A/ko not_active Withdrawn
- 2008-06-04 CA CA2694860A patent/CA2694860A1/en not_active Abandoned
- 2008-06-04 MX MX2009013333A patent/MX2009013333A/es active IP Right Grant
- 2008-06-04 WO PCT/US2008/006979 patent/WO2008153858A1/en not_active Ceased
- 2008-06-04 MY MYPI20095228A patent/MY148609A/en unknown
- 2008-06-04 CL CL2008001633A patent/CL2008001633A1/es unknown
- 2008-06-04 RU RU2009148867/04A patent/RU2475484C2/ru not_active IP Right Cessation
-
2009
- 2009-11-24 IL IL202317A patent/IL202317A0/en unknown
- 2009-11-30 ZA ZA2009/08477A patent/ZA200908477B/en unknown
- 2009-12-03 EC EC2009009781A patent/ECSP099781A/es unknown
- 2009-12-04 CO CO09139231A patent/CO6251261A2/es active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0812450A2 (pt) | 2019-09-24 |
| IL202317A0 (en) | 2010-06-30 |
| ZA200908477B (en) | 2012-05-30 |
| EP2155722A1 (en) | 2010-02-24 |
| PE20090326A1 (es) | 2009-04-04 |
| EP2155722B1 (en) | 2013-08-14 |
| AR068046A1 (es) | 2009-11-04 |
| NZ581698A (en) | 2012-09-28 |
| MX2009013333A (es) | 2010-01-18 |
| AU2008262412A1 (en) | 2008-12-18 |
| WO2008153858A1 (en) | 2008-12-18 |
| CA2694860A1 (en) | 2008-12-18 |
| JP2010529122A (ja) | 2010-08-26 |
| KR20100025553A (ko) | 2010-03-09 |
| AU2008262412A2 (en) | 2010-01-07 |
| TW200911262A (en) | 2009-03-16 |
| RU2475484C2 (ru) | 2013-02-20 |
| CO6251261A2 (es) | 2011-02-21 |
| MY148609A (en) | 2013-05-15 |
| CN101815711A (zh) | 2010-08-25 |
| RU2009148867A (ru) | 2011-07-20 |
| CL2008001633A1 (es) | 2008-12-12 |
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