KR20200046053A - 스피로사이클 화합물 및 이를 제조하고 사용하는 방법 - Google Patents
스피로사이클 화합물 및 이를 제조하고 사용하는 방법 Download PDFInfo
- Publication number
- KR20200046053A KR20200046053A KR1020207007712A KR20207007712A KR20200046053A KR 20200046053 A KR20200046053 A KR 20200046053A KR 1020207007712 A KR1020207007712 A KR 1020207007712A KR 20207007712 A KR20207007712 A KR 20207007712A KR 20200046053 A KR20200046053 A KR 20200046053A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- pharmaceutically acceptable
- compound
- solvate
- hydrate
- 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.)
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 951
- 238000000034 method Methods 0.000 title claims description 51
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- 238000011282 treatment Methods 0.000 claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims description 1023
- 239000012453 solvate Substances 0.000 claims description 1004
- 125000000217 alkyl group Chemical group 0.000 claims description 536
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 422
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 385
- 229910052736 halogen Inorganic materials 0.000 claims description 287
- 150000002367 halogens Chemical class 0.000 claims description 287
- 229910052739 hydrogen Inorganic materials 0.000 claims description 250
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 214
- 229910052757 nitrogen Inorganic materials 0.000 claims description 211
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 198
- 150000004677 hydrates Chemical class 0.000 claims description 174
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 148
- 229910052799 carbon Inorganic materials 0.000 claims description 140
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 130
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 130
- 229910052698 phosphorus Inorganic materials 0.000 claims description 130
- 239000011574 phosphorus Substances 0.000 claims description 130
- 125000001072 heteroaryl group Chemical group 0.000 claims description 126
- 125000003118 aryl group Chemical group 0.000 claims description 101
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 96
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 66
- 125000004043 oxo group Chemical group O=* 0.000 claims description 59
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 27
- 125000000304 alkynyl group Chemical group 0.000 claims description 24
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- 208000035475 disorder Diseases 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 11
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- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
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- 235000002639 sodium chloride Nutrition 0.000 description 930
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 40
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- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 7
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 6
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 5
- 125000004404 heteroalkyl group Chemical group 0.000 description 5
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- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
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- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
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- 150000007513 acids Chemical class 0.000 description 3
- 125000004419 alkynylene group Chemical group 0.000 description 3
- 150000005840 aryl radicals Chemical group 0.000 description 3
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- 210000004027 cell Anatomy 0.000 description 3
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- 229910052760 oxygen Inorganic materials 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical group C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical group C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
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Classifications
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- 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
-
- 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
- A61K31/438—The ring being spiro-condensed with carbocyclic or heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- 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
- 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
- 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
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- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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| MX350788B (es) | 2012-01-06 | 2017-09-13 | Abide Therapeutics Inc | Compuestos de carbamato y preparación y uso de los mismos. |
| WO2017197192A1 (en) | 2016-05-12 | 2017-11-16 | Abide Therapeutics, Inc. | Spirocycle compounds and methods of making and using same |
| WO2018053447A1 (en) | 2016-09-19 | 2018-03-22 | Abide Therapeutics, Inc. | Piperazine carbamates and methods of making and using same |
| JOP20190107A1 (ar) | 2016-11-16 | 2019-05-09 | Lundbeck La Jolla Research Center Inc | مثبطات أحادي أسيل جليسرول ليباز (magl) |
| MX2020002251A (es) | 2017-08-29 | 2020-07-20 | Lundbeck La Jolla Research Center Inc | Compuestos espirociclicos y sus metodos de preparacion y uso. |
| US11161856B2 (en) | 2017-08-29 | 2021-11-02 | H. Lundbeck A/S | Spirocycle compounds and methods of making and using same |
| CN112088001A (zh) | 2018-05-15 | 2020-12-15 | 隆德贝克拉荷亚研究中心有限公司 | Magl抑制剂 |
| CN111505410B (zh) * | 2020-04-02 | 2022-07-29 | 矽力杰半导体技术(杭州)有限公司 | 调光模式检测电路、方法和无调光检测电路及照明系统 |
| IL297470A (en) | 2020-04-21 | 2022-12-01 | H Lundbeck As | Synthesis of a monoacylglycerol lipase inhibitor |
| UY39516A (es) * | 2020-11-13 | 2022-05-31 | H Lundbeck As | Composición para el tratamiento de una enfermedad vascular, composición para la prevención de una enfermedad vascular, composición para el tratamiento de la hipertensión, y composición para la prevención de la hipertensión |
| US20240174680A1 (en) | 2021-01-29 | 2024-05-30 | Cedilla Therapeutics, Inc. | Cdk2 inhibitors and methods of using the same |
| US12053459B2 (en) | 2021-06-26 | 2024-08-06 | Cedilla Therapeutics, Inc. | CDK2 inhibitors and methods of using the same |
| US20250084065A1 (en) | 2021-12-29 | 2025-03-13 | Psy Therapeutics, Inc. | Inhibiting monoacylglycerol lipase (magl) |
| US12378219B2 (en) * | 2022-05-04 | 2025-08-05 | H. Lundbeck A/S | Crystalline forms of a MAGL inhibitor |
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| CA2665804A1 (en) * | 2006-08-23 | 2008-02-28 | Astellas Pharma Inc. | Urea compound or salt thereof |
| CA2716863A1 (en) | 2008-03-05 | 2009-09-11 | Targacept, Inc. | Sub-type selective amides of diazabicycloalkanes |
| US20120083476A1 (en) | 2009-06-05 | 2012-04-05 | Janssen Pharmaceutica Nv | Heteroaryl-substituted spirocyclic diamine urea modulators of fatty acid amide hydrolase |
| DK3093291T3 (da) | 2009-10-23 | 2019-07-29 | Janssen Pharmaceutica Nv | Disubstituerede octahy-dropyrrolo [3,4-c]pyrroler som orexinreceptormodulatorer |
| WO2011109277A1 (en) | 2010-03-04 | 2011-09-09 | Merck Sharp & Dohme Corp. | Positive allosteric modulators of mglur2 |
| FR2960875B1 (fr) | 2010-06-04 | 2012-12-28 | Sanofi Aventis | Derives de carbamates d'hexafluoroisopropyle, leur preparation et leur application en therapeutique |
| EP2444084A1 (en) | 2010-10-21 | 2012-04-25 | Centro Nacional de Investigaciones Oncológicas (CNIO) | Use of PI3K inibitors for the treatment of obesity |
| MX350788B (es) | 2012-01-06 | 2017-09-13 | Abide Therapeutics Inc | Compuestos de carbamato y preparación y uso de los mismos. |
| RS59512B1 (sr) | 2012-09-25 | 2019-12-31 | Hoffmann La Roche | Derivati heksahidropirolo[3,4−c]pirola i srodna jedinjenja kao inhibitori autotaksina (atx) i kao inhibitori proizvodnje lizofosfatidne kiseline (lpa) za lečenje npr. bubrežnih bolesti |
| CA2917050A1 (en) | 2013-07-03 | 2015-01-08 | Todd K. Jones | Pyrrolo-pyrrole carbamate and related organic compounds, pharmaceutical compositions, and medical uses thereof |
| US9771341B2 (en) * | 2015-03-18 | 2017-09-26 | Abide Therapeutics, Inc. | Piperazine carbamates and methods of making and using same |
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| CN108601769B (zh) * | 2015-11-20 | 2021-09-03 | H.隆德贝克有限公司 | 吡唑化合物及其制备和使用方法 |
| WO2017197192A1 (en) | 2016-05-12 | 2017-11-16 | Abide Therapeutics, Inc. | Spirocycle compounds and methods of making and using same |
| JOP20190107A1 (ar) | 2016-11-16 | 2019-05-09 | Lundbeck La Jolla Research Center Inc | مثبطات أحادي أسيل جليسرول ليباز (magl) |
| US11161856B2 (en) | 2017-08-29 | 2021-11-02 | H. Lundbeck A/S | Spirocycle compounds and methods of making and using same |
| MX2020002251A (es) | 2017-08-29 | 2020-07-20 | Lundbeck La Jolla Research Center Inc | Compuestos espirociclicos y sus metodos de preparacion y uso. |
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| JOP20200022A1 (ar) | 2020-02-02 |
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| BR112020003946A2 (pt) | 2020-09-08 |
| ECSP20013332A (es) | 2020-04-22 |
| CL2020000463A1 (es) | 2020-07-10 |
| CN111032034B (zh) | 2023-05-02 |
| AU2018326497A1 (en) | 2020-02-20 |
| EP3675848A1 (en) | 2020-07-08 |
| US11161856B2 (en) | 2021-11-02 |
| CR20200088A (es) | 2020-04-08 |
| PH12020500371A1 (en) | 2020-12-07 |
| PE20200665A1 (es) | 2020-06-11 |
| JP2020532547A (ja) | 2020-11-12 |
| EP3675848A4 (en) | 2021-03-10 |
| CO2020001715A2 (es) | 2020-02-28 |
| RU2020107039A (ru) | 2021-09-30 |
| IL272578A (en) | 2020-03-31 |
| US20210214375A1 (en) | 2021-07-15 |
| MX2020002254A (es) | 2020-07-20 |
| SG11202000984YA (en) | 2020-03-30 |
| EA202090296A1 (ru) | 2020-08-03 |
| MA50045A (fr) | 2020-07-08 |
| CN111032034A (zh) | 2020-04-17 |
| JP7177825B2 (ja) | 2022-11-24 |
| EP3675848B1 (en) | 2022-03-23 |
| ES2914363T3 (es) | 2022-06-09 |
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