MX2017009408A - Compuestos antihelminticos, composiciones y metodo para usar los mismos. - Google Patents
Compuestos antihelminticos, composiciones y metodo para usar los mismos.Info
- Publication number
- MX2017009408A MX2017009408A MX2017009408A MX2017009408A MX2017009408A MX 2017009408 A MX2017009408 A MX 2017009408A MX 2017009408 A MX2017009408 A MX 2017009408A MX 2017009408 A MX2017009408 A MX 2017009408A MX 2017009408 A MX2017009408 A MX 2017009408A
- Authority
- MX
- Mexico
- Prior art keywords
- compounds
- compositions
- ring
- anthelmintic compounds
- alkoxyalkyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 4
- 230000000507 anthelmentic effect Effects 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 title abstract 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000001188 haloalkyl group Chemical group 0.000 abstract 2
- 125000001072 heteroaryl group Chemical group 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 206010061217 Infestation Diseases 0.000 abstract 1
- 241001465754 Metazoa Species 0.000 abstract 1
- 208000015181 infectious disease Diseases 0.000 abstract 1
- 230000003071 parasitic effect Effects 0.000 abstract 1
- 230000000590 parasiticidal effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- 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
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
-
- 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
- C07D401/02—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
-
- 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
- C07D405/02—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 two hetero rings
- C07D405/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D417/02—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 two hetero rings
- C07D417/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
La presente invención se relaciona a compuestos antihelmínticos novedosos de la fórmula (IA) enseguida: en donde, Y se selecciona del grupo que consiste de -H, arilo, cicloalquilo, cicloalquenilo, heteroarilo, heterociclilo, alquilo, haloalquilo y alcoxialquilo; y Z se selecciona del grupo que consiste de arilo, cicloalquilo, cicloalquenilo, heteroarilo, heterociclilo, alquilo, haloalquilo y alcoxialquilo. Las variables Anillo A, Anillo B, Anillo C, X1, X6 y X8 son como se definen en la presente. La invención también se relaciona a composiciones parasiticidas que comprenden los compuestos, y métodos y usos de los compuestos para tratar y prevenir infecciones e infestaciones parasíticas en animales.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562105463P | 2015-01-20 | 2015-01-20 | |
| PCT/US2016/014148 WO2016118638A1 (en) | 2015-01-20 | 2016-01-20 | Anthelmintic compounds, compositions and method of using thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MX2017009408A true MX2017009408A (es) | 2017-10-02 |
| MX379304B MX379304B (es) | 2025-03-11 |
Family
ID=55299781
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2017009408A MX379304B (es) | 2015-01-20 | 2016-01-20 | Compuestos antihelminticos, composiciones y metodo para usar los mismos. |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US10597364B2 (es) |
| EP (1) | EP3247701B1 (es) |
| JP (1) | JP6771469B2 (es) |
| CN (1) | CN107257793A (es) |
| AU (3) | AU2016209321B2 (es) |
| BR (1) | BR112017015273A2 (es) |
| CA (1) | CA2973873A1 (es) |
| ES (1) | ES2907461T3 (es) |
| MX (1) | MX379304B (es) |
| NZ (1) | NZ734082A (es) |
| WO (1) | WO2016118638A1 (es) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2545964A1 (en) | 2011-07-13 | 2013-01-16 | Phenex Pharmaceuticals AG | Novel FXR (NR1H4) binding and activity modulating compounds |
| CA2968836C (en) | 2016-06-13 | 2025-09-02 | Gilead Sciences, Inc. | FXR MODULATING COMPOUNDS (NR1H4) |
| ES2921432T3 (es) | 2016-06-13 | 2022-08-25 | Gilead Sciences Inc | Derivados de azetidina como moduladores de FXR (NR1H4) |
| US10710980B2 (en) | 2016-07-20 | 2020-07-14 | Novartis Ag | Aminopyridine derivatives and their use as selective ALK-2 inhibitors |
| EP4424364B1 (en) | 2017-03-28 | 2026-01-21 | Gilead Sciences, Inc. | Combinations for use in the treatment of cirrhosis and liver fibrosis |
| RU2020105929A (ru) | 2017-08-04 | 2021-09-06 | Скайхоук Терапьютикс, Инк. | Способы и композиции для модулирования сплайсинга |
| TWI793151B (zh) | 2017-08-23 | 2023-02-21 | 瑞士商諾華公司 | 3-(1-氧異吲哚啉-2-基)之氫吡啶-2,6-二酮衍生物及其用途 |
| BR122022012697B1 (pt) | 2018-07-10 | 2023-04-04 | Novartis Ag | Usos de derivados de 3-(5-hidróxi-1-oxoisoindolin-2-il)piperidina-2,6- diona, e kit |
| AR116109A1 (es) | 2018-07-10 | 2021-03-31 | Novartis Ag | Derivados de 3-(5-amino-1-oxoisoindolin-2-il)piperidina-2,6-diona y usos de los mismos |
| AR116524A1 (es) * | 2018-10-04 | 2021-05-19 | Elanco Tiergesundheit Ag | Potenciación de tratamiento de helmintos |
| TWI767148B (zh) | 2018-10-10 | 2022-06-11 | 美商弗瑪治療公司 | 抑制脂肪酸合成酶(fasn) |
| GB201820626D0 (en) * | 2018-12-18 | 2019-01-30 | Univ Of Canterbury | Conjugates |
| PE20211907A1 (es) | 2019-01-15 | 2021-09-28 | Gilead Sciences Inc | Compuestos moduladores de fxr (nr1h4) |
| RS66416B1 (sr) | 2019-01-18 | 2025-02-28 | Astrazeneca Ab | 6'-[[(1s,3s)-3-[[5-(difluorometoksi)-2-pirimidinil]amino]ciklopentil]amino][1(2h),3'-bipiridin]-2-on kao inhibitor pcsk9 i metode njegove primene |
| EP3911640A4 (en) | 2019-01-18 | 2022-10-26 | Astrazeneca AB | PCSK9 INHIBITORS AND METHODS OF USE THEREOF |
| EP3920926A4 (en) | 2019-02-05 | 2022-10-19 | Skyhawk Therapeutics, Inc. | Methods and compositions for modulating splicing |
| JP7603592B2 (ja) | 2019-02-05 | 2024-12-20 | スカイホーク・セラピューティクス・インコーポレーテッド | スプライシングを調節するための方法および組成物 |
| WO2020163544A1 (en) | 2019-02-06 | 2020-08-13 | Skyhawk Therapeutics, Inc. | Methods and compositions for modulating splicing |
| CN119638696A (zh) | 2019-02-06 | 2025-03-18 | 斯基霍克疗法公司 | 用于调节剪接的方法和组合物 |
| KR102725082B1 (ko) | 2019-02-19 | 2024-11-04 | 길리애드 사이언시즈, 인코포레이티드 | Fxr 효능제의 고체 형태 |
| BR112021018631A2 (pt) * | 2019-03-19 | 2021-11-23 | Boehringer Ingelheim Animal Health Usa Inc | Compostos anti-helmínticos de aza-benzotiofeno e aza-benzofurano |
| UY38687A (es) | 2019-05-17 | 2023-05-15 | Novartis Ag | Inhibidores del inflamasoma nlrp3, composiciones, combinaciones de los mismos y métodos para su uso |
| US11129829B2 (en) | 2019-06-17 | 2021-09-28 | Skyhawk Therapeutics, Inc. | Methods for modulating splicing |
| JP7558267B2 (ja) | 2019-10-25 | 2024-09-30 | ギリアード サイエンシーズ, インコーポレイテッド | Glp-1r調節化合物 |
| JP7717065B2 (ja) | 2019-11-22 | 2025-08-01 | インサイト コーポレーション | Alk2阻害剤及びjak2阻害剤を含む併用療法 |
| CN120518596A (zh) | 2020-01-29 | 2025-08-22 | 吉利德科学公司 | Glp-1r调节化合物 |
| IL297128A (en) | 2020-04-07 | 2022-12-01 | Mitobridge Inc | Cd38 inhibitors |
| BR112022023199A2 (pt) | 2020-05-15 | 2023-04-04 | Algen Biotechnologies Inc | Certas composições químicas e métodos de uso das mesmas |
| AU2021292484A1 (en) | 2020-06-16 | 2023-01-19 | Incyte Corporation | ALK2 inhibitors for the treatment of anemia |
| US11851419B2 (en) | 2020-11-20 | 2023-12-26 | Gilead Sciences, Inc. | GLP-1R modulating compounds |
| EP4304712A1 (en) | 2021-03-11 | 2024-01-17 | Gilead Sciences, Inc. | Glp-1r modulating compounds |
| US12091404B2 (en) | 2021-03-11 | 2024-09-17 | Gilead Sciences, Inc. | GLP-1R modulating compounds |
| US11932630B2 (en) | 2021-04-16 | 2024-03-19 | Novartis Ag | Heteroaryl aminopropanol derivatives |
| IL306110A (en) | 2021-04-21 | 2023-11-01 | Gilead Sciences Inc | Carboxy-benzimidazole glp-1r modulating compounds |
| UY40374A (es) | 2022-08-03 | 2024-02-15 | Novartis Ag | Inhibidores de inflamasoma nlrp3 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4208254A1 (de) | 1992-03-14 | 1993-09-16 | Hoechst Ag | Substituierte pyrimidine, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel und fungizid |
| AU1631699A (en) | 1997-12-18 | 1999-07-05 | E.I. Du Pont De Nemours And Company | Cyclohexylamine arthropodicides and fungicides |
| US20010049373A1 (en) | 2000-01-28 | 2001-12-06 | Chalquest Richard R. | Materials and methods for killing nematodes and nematode eggs |
| US7199147B2 (en) | 2001-06-12 | 2007-04-03 | Dainippon Sumitomo Pharma Co., Ltd. | Rho kinase inhibitors |
| US7582645B2 (en) * | 2003-10-10 | 2009-09-01 | Bayer Pharmaceuticals Corporation | Pyrimidine derivatives for treatment of hyperproliferative disorders |
| MXPA06012613A (es) * | 2004-05-07 | 2007-01-31 | Amgen Inc | Derivados heterociclicos nitrogenados como moduladores de proteina cinasa y uso para el tratamiento de angiogenesis y cancer. |
| DE102005032838A1 (de) * | 2005-07-14 | 2007-02-08 | Merck Patent Gmbh | Mischung von Onium-Alkylsulfonaten und Onium-Alkylsulfiten |
| WO2007063839A1 (ja) * | 2005-11-30 | 2007-06-07 | Shionogi & Co., Ltd. | シクロヘキサン誘導体 |
| TW200938203A (en) | 2007-12-17 | 2009-09-16 | Intervet Int Bv | Anthelmintic agents and their use |
| TW201041868A (en) | 2009-03-20 | 2010-12-01 | Intervet Int Bv | Anthelmintic agents and their use |
| TW201111358A (en) | 2009-06-18 | 2011-04-01 | Intervet Int Bv | Anthelmintic agents and their use |
| AU2010303780B2 (en) | 2009-10-09 | 2014-02-20 | Irm Llc | Compounds and compositions as modulators of GPR119 activity |
| US8952037B2 (en) * | 2010-05-13 | 2015-02-10 | Amgen Inc. | Heteroaryloxycarbocyclyl compounds as PDE10 inhibitors |
| US8497265B2 (en) * | 2010-05-13 | 2013-07-30 | Amgen Inc. | Heteroaryloxyheterocyclyl compounds as PDE10 inhibitors |
| EP2468096A1 (en) | 2010-12-21 | 2012-06-27 | Intervet International BV | Anthelmintic combinations |
| US8530461B2 (en) * | 2011-12-29 | 2013-09-10 | Boehringer Ingelheim International Gmbh | Azetidine derivatives |
| AU2013301533B2 (en) * | 2012-08-08 | 2016-02-25 | Elanco Tiergesundheit Ag | Subtituted azines as pesticides |
| SG11201503959VA (en) | 2012-11-20 | 2015-06-29 | Merial Inc | Anthelmintic compounds and compositions and method of using thereof |
| SMT202100687T1 (it) | 2013-03-12 | 2022-01-10 | Vertex Pharma | Inibitori della dna-pk |
| CA2926700C (en) | 2013-11-18 | 2018-03-20 | Novartis Tiergesundheit Ag | Pyridyl, pyrimidinyl and phenyl compounds and their use in the control of parasites |
| US10045979B2 (en) | 2014-05-19 | 2018-08-14 | Merial Inc. | Anthelmintic compounds |
-
2016
- 2016-01-20 ES ES16702865T patent/ES2907461T3/es active Active
- 2016-01-20 US US15/544,837 patent/US10597364B2/en active Active
- 2016-01-20 JP JP2017538327A patent/JP6771469B2/ja not_active Expired - Fee Related
- 2016-01-20 MX MX2017009408A patent/MX379304B/es unknown
- 2016-01-20 CA CA2973873A patent/CA2973873A1/en not_active Abandoned
- 2016-01-20 NZ NZ734082A patent/NZ734082A/en not_active IP Right Cessation
- 2016-01-20 AU AU2016209321A patent/AU2016209321B2/en not_active Ceased
- 2016-01-20 EP EP16702865.3A patent/EP3247701B1/en active Active
- 2016-01-20 CN CN201680010899.2A patent/CN107257793A/zh active Pending
- 2016-01-20 BR BR112017015273-8A patent/BR112017015273A2/pt active Search and Examination
- 2016-01-20 WO PCT/US2016/014148 patent/WO2016118638A1/en not_active Ceased
-
2019
- 2019-04-18 AU AU2019202773A patent/AU2019202773B2/en not_active Ceased
-
2020
- 2020-06-30 AU AU2020204400A patent/AU2020204400A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JP6771469B2 (ja) | 2020-10-21 |
| US10597364B2 (en) | 2020-03-24 |
| WO2016118638A1 (en) | 2016-07-28 |
| US20180009754A1 (en) | 2018-01-11 |
| AU2019202773A1 (en) | 2019-05-16 |
| CA2973873A1 (en) | 2016-07-28 |
| AU2019202773B2 (en) | 2020-07-02 |
| JP2018502877A (ja) | 2018-02-01 |
| EP3247701A1 (en) | 2017-11-29 |
| MX379304B (es) | 2025-03-11 |
| ES2907461T3 (es) | 2022-04-25 |
| NZ734082A (en) | 2019-01-25 |
| EP3247701B1 (en) | 2021-09-22 |
| AU2020204400A1 (en) | 2020-07-30 |
| AU2016209321A1 (en) | 2017-08-17 |
| CN107257793A (zh) | 2017-10-17 |
| AU2016209321B2 (en) | 2019-05-09 |
| BR112017015273A2 (pt) | 2018-01-09 |
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