KR102148679B1 - Pi3 키나제 모듈레이터로서의 헤테로방향족 화합물 및 이의 이용 방법 - Google Patents
Pi3 키나제 모듈레이터로서의 헤테로방향족 화합물 및 이의 이용 방법 Download PDFInfo
- Publication number
- KR102148679B1 KR102148679B1 KR1020157008264A KR20157008264A KR102148679B1 KR 102148679 B1 KR102148679 B1 KR 102148679B1 KR 1020157008264 A KR1020157008264 A KR 1020157008264A KR 20157008264 A KR20157008264 A KR 20157008264A KR 102148679 B1 KR102148679 B1 KR 102148679B1
- Authority
- KR
- South Korea
- Prior art keywords
- cancer
- compound
- mmol
- alkylene
- alkyl
- 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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Links
- DKHYPLPGPFVNOD-UHFFFAOYSA-N CC(C#Cc1nnc(cc2)[n]1cc2-c(cc1NS(c(ccc(F)c2)c2F)(=O)=O)cnc1OC)O Chemical compound CC(C#Cc1nnc(cc2)[n]1cc2-c(cc1NS(c(ccc(F)c2)c2F)(=O)=O)cnc1OC)O DKHYPLPGPFVNOD-UHFFFAOYSA-N 0.000 description 2
- QOKSIKUFPUHKJE-UHFFFAOYSA-N CC#Cc1nnc(cc2)[n]1nc2-c(cc1NS(c(cc2)ccc2F)(=O)=O)cnc1OC Chemical compound CC#Cc1nnc(cc2)[n]1nc2-c(cc1NS(c(cc2)ccc2F)(=O)=O)cnc1OC QOKSIKUFPUHKJE-UHFFFAOYSA-N 0.000 description 1
- OMPGUOJYQSOZAM-UHFFFAOYSA-N CC(C#Cc1cnc(cc2)[n]1nc2-c(cc1NS(c(cc2)ccc2F)(=O)=O)cnc1OC)O Chemical compound CC(C#Cc1cnc(cc2)[n]1nc2-c(cc1NS(c(cc2)ccc2F)(=O)=O)cnc1OC)O OMPGUOJYQSOZAM-UHFFFAOYSA-N 0.000 description 1
- LABGKPJMYVBXOG-UHFFFAOYSA-N CC(C)(C#Cc1nnc(cc2)[n]1nc2-c(cc1NS(c(ccc(F)c2)c2F)(=O)=O)cnc1OC)O Chemical compound CC(C)(C#Cc1nnc(cc2)[n]1nc2-c(cc1NS(c(ccc(F)c2)c2F)(=O)=O)cnc1OC)O LABGKPJMYVBXOG-UHFFFAOYSA-N 0.000 description 1
- KXAJBXOSGXYSLA-BEVBOREHSA-N COC1NC=C[C@@H](Cc(cc2)n[n]3c2ncc3C#N)C1NS(c(ccc(F)c1)c1F)(=O)=O Chemical compound COC1NC=C[C@@H](Cc(cc2)n[n]3c2ncc3C#N)C1NS(c(ccc(F)c1)c1F)(=O)=O KXAJBXOSGXYSLA-BEVBOREHSA-N 0.000 description 1
- VCOYQUMRFXOYPX-UHFFFAOYSA-N COc(c(NS(c(cc1)ccc1F)(=O)=O)c1)ncc1-c(cc1)n[n]2c1ncc2C#C Chemical compound COc(c(NS(c(cc1)ccc1F)(=O)=O)c1)ncc1-c(cc1)n[n]2c1ncc2C#C VCOYQUMRFXOYPX-UHFFFAOYSA-N 0.000 description 1
- MVIFBXKSXVSARX-UHFFFAOYSA-N COc(c(NS(c(cc1)ccc1F)(=O)=O)c1)ncc1-c1n[n]2c(C#C)nnc2cc1 Chemical compound COc(c(NS(c(cc1)ccc1F)(=O)=O)c1)ncc1-c1n[n]2c(C#C)nnc2cc1 MVIFBXKSXVSARX-UHFFFAOYSA-N 0.000 description 1
- JUBPIVKFOHWHFK-UHFFFAOYSA-N COc(c(NS(c(cc1)ccc1F)(=O)=O)c1)ncc1-c1n[n]2c(C#CCO)nnc2cc1 Chemical compound COc(c(NS(c(cc1)ccc1F)(=O)=O)c1)ncc1-c1n[n]2c(C#CCO)nnc2cc1 JUBPIVKFOHWHFK-UHFFFAOYSA-N 0.000 description 1
- OVJAQOUIWYXPSM-UHFFFAOYSA-N COc(c(NS(c(ccc(F)c1)c1F)(=O)=O)c1)ncc1-c(cc1)n[n]2c1ncc2C#CCO Chemical compound COc(c(NS(c(ccc(F)c1)c1F)(=O)=O)c1)ncc1-c(cc1)n[n]2c1ncc2C#CCO OVJAQOUIWYXPSM-UHFFFAOYSA-N 0.000 description 1
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
- A61K31/495—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
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic 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
- A61K31/435—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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
-
- 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
- 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
- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (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)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261726139P | 2012-11-14 | 2012-11-14 | |
| US61/726,139 | 2012-11-14 | ||
| PCT/US2013/069366 WO2014078211A1 (en) | 2012-11-14 | 2013-11-10 | Heteroaromatic compounds as pi3 kinase modulators and methods of use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20150083833A KR20150083833A (ko) | 2015-07-20 |
| KR102148679B1 true KR102148679B1 (ko) | 2020-08-27 |
Family
ID=50681898
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020157008264A Active KR102148679B1 (ko) | 2012-11-14 | 2013-11-10 | Pi3 키나제 모듈레이터로서의 헤테로방향족 화합물 및 이의 이용 방법 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US9926324B2 (enExample) |
| EP (2) | EP3299019B1 (enExample) |
| JP (1) | JP6268183B2 (enExample) |
| KR (1) | KR102148679B1 (enExample) |
| CN (1) | CN104755085B (enExample) |
| AU (1) | AU2013345107B2 (enExample) |
| BR (1) | BR112015006726B1 (enExample) |
| CA (1) | CA2889346C (enExample) |
| ES (1) | ES2661380T3 (enExample) |
| MY (1) | MY180641A (enExample) |
| RU (1) | RU2665036C9 (enExample) |
| SG (1) | SG11201502725TA (enExample) |
| TW (1) | TWI574962B (enExample) |
| WO (1) | WO2014078211A1 (enExample) |
| ZA (1) | ZA201502575B (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104496940B (zh) * | 2014-01-06 | 2017-03-15 | 广东东阳光药业有限公司 | 一种制备bcr‑abl抑制剂中间体的方法 |
| BR112016029825B1 (pt) * | 2014-06-17 | 2020-10-27 | Cisen Pharmaceutical Co., Ltd. | composto |
| CN105503877A (zh) * | 2014-09-24 | 2016-04-20 | 和记黄埔医药（上海）有限公司 | 咪唑并哒嗪类化合物及其用途 |
| JP6568588B2 (ja) | 2014-12-19 | 2019-08-28 | ヤンセン ファーマシューティカ エヌ．ベー． | ＰＩ３Ｋβ阻害剤としてのイミダゾピリダジン誘導体 |
| HRP20192162T1 (hr) | 2014-12-19 | 2020-02-21 | Janssen Pharmaceutica N.V. | Heterociklil vezani derivati imidazopiridazina kao inhibitori pi3kbeta |
| CA3025594C (en) * | 2016-06-16 | 2024-06-18 | Janssen Pharmaceutica Nv | Bicyclic pyridine, pyrazine, and pyrimidine derivatives as pi3k beta inhibitors |
| WO2018017633A1 (en) | 2016-07-21 | 2018-01-25 | Bristol-Myers Squibb Company | TGF Beta RECEPTOR ANTAGONISTS |
| WO2018068759A1 (zh) | 2016-10-14 | 2018-04-19 | 江苏恒瑞医药股份有限公司 | 五元杂芳环并桥环类衍生物、其制备方法及其在医药上的应用 |
| JP7105797B2 (ja) * | 2016-11-28 | 2022-07-25 | プラクシス プレシジョン メディシンズ， インコーポレイテッド | 化合物及びその使用方法 |
| CN108164525B (zh) * | 2016-12-08 | 2020-09-08 | 沈阳药科大学 | 一种抗肿瘤化合物的制备方法和用途 |
| JP7300394B2 (ja) | 2017-01-17 | 2023-06-29 | ヘパリジェニックス ゲーエムベーハー | 肝再生の促進又は肝細胞死の低減もしくは予防のためのプロテインキナーゼ阻害 |
| FR3064364A1 (fr) * | 2017-03-27 | 2018-09-28 | S.P.C.M. Sa | Methode de dosage de polymeres cationiques |
| KR102797536B1 (ko) | 2020-04-29 | 2025-04-22 | 릴레이 테라퓨틱스, 인크. | PI3Kα 억제제 및 이의 사용 방법 |
| EP4399196A4 (en) * | 2021-09-10 | 2025-08-06 | Relay Therapeutics Inc | PI3K-ALPHA INHIBITORS AND METHODS OF USE THEREOF |
| JP2025519029A (ja) * | 2022-05-10 | 2025-06-24 | リレー セラピューティクス， インコーポレイテッド | ＰＩ３Ｋα阻害剤及びその使用方法 |
| CN120737113B (zh) * | 2025-09-03 | 2025-11-21 | 湖北师范大学 | 一种三唑并哒嗪类化合物区域选择性c3-h炔基化的方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011500823A (ja) | 2007-10-22 | 2011-01-06 | グラクソスミスクライン・リミテッド・ライアビリティ・カンパニー | Ｐｉ３キナーゼ阻害物質としてのピリドスルホンアミド誘導体 |
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| RU2036924C1 (ru) * | 1989-01-31 | 1995-06-09 | Такеда Кемикал Индастриз ЛТД | Способ получения производных имидазо (1,2-b)пиридазина или их солей и производные имидазо (1,2-b)пиридазина или их соли |
| US5304121A (en) | 1990-12-28 | 1994-04-19 | Boston Scientific Corporation | Drug delivery system making use of a hydrogel polymer coating |
| US5886026A (en) | 1993-07-19 | 1999-03-23 | Angiotech Pharmaceuticals Inc. | Anti-angiogenic compositions and methods of use |
| CA2177031A1 (en) | 1993-11-30 | 1995-06-08 | Moshe Szyf | Inhibition of dna methyltransferase |
| US5578716A (en) | 1993-12-01 | 1996-11-26 | Mcgill University | DNA methyltransferase antisense oligonucleotides |
| US6099562A (en) | 1996-06-13 | 2000-08-08 | Schneider (Usa) Inc. | Drug coating with topcoat |
| US6268137B1 (en) | 1996-05-22 | 2001-07-31 | Methylgene, Inc. | Specific inhibitors of DNA methyl transferase |
| US6020318A (en) | 1997-05-30 | 2000-02-01 | Methylgene, Inc. | DNA methyltransferase genomic sequences and antisense oligonucleotides |
| AU8125098A (en) | 1997-05-30 | 1998-12-30 | Mcgill University | Dna methyltransferase genomic sequences and antisense oligonucleotides |
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| JP2003500052A (ja) | 1999-05-03 | 2003-01-07 | メチルジーン インコーポレイテッド | ヒストン脱アセチル酵素の抑制 |
| WO2001038322A1 (en) | 1999-11-23 | 2001-05-31 | Methylgene, Inc. | Inhibitors of histone deacetylase |
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| KR20100107509A (ko) | 2001-09-14 | 2010-10-05 | 9222-9129 퀘벡 인코포레이티드 | 히스톤 데아세틸라아제의 억제제 |
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| WO2009133127A1 (en) * | 2008-04-30 | 2009-11-05 | Merck Serono S.A. | Fused bicyclic compounds and use thereof as pi3k inhibitors |
| KR101721280B1 (ko) | 2009-08-17 | 2017-03-29 | 인텔리카인, 엘엘씨 | 헤테로사이클릭 화합물 및 이의 용도 |
| EP2571357B1 (en) * | 2010-05-21 | 2016-07-06 | Infinity Pharmaceuticals, Inc. | Chemical compounds, compositions and methods for kinase modulation |
| UY33597A (es) * | 2010-09-09 | 2012-04-30 | Irm Llc | Compuestos y composiciones como inhibidores de la trk |
| RU2598840C2 (ru) | 2011-05-19 | 2016-09-27 | Фундасион Сентро Насиональ Де Инвестигасионес Онколохикас Карлос Iii | Новые соединения |
| WO2012174312A2 (en) | 2011-06-15 | 2012-12-20 | Glaxosmithkline Llc | Benzimidazole derivatives as antiviral agents |
| KR101274986B1 (ko) | 2011-07-27 | 2013-06-17 | 한국과학기술원 | 이미다조피리딘 유도체, 이를 포함하는 ＰＩ3Ｋ 및/또는 ｍＴＯＲ 저해제용 약학 조성물 및 ＰＩ3Ｋ 및/또는 ｍＴＯＲ과 연관된 질환 치료용 약학 조성물 |
| GB201205669D0 (en) | 2012-03-30 | 2012-05-16 | Agency Science Tech & Res | Bicyclic heterocyclic derivatives as mnk2 and mnk2 modulators and uses thereof |
-
2013
- 2013-11-08 TW TW102140742A patent/TWI574962B/zh active
- 2013-11-10 WO PCT/US2013/069366 patent/WO2014078211A1/en not_active Ceased
- 2013-11-10 RU RU2015116102A patent/RU2665036C9/ru active
- 2013-11-10 CA CA2889346A patent/CA2889346C/en active Active
- 2013-11-10 MY MYPI2015701411A patent/MY180641A/en unknown
- 2013-11-10 EP EP17192050.7A patent/EP3299019B1/en active Active
- 2013-11-10 ES ES13855522.2T patent/ES2661380T3/es active Active
- 2013-11-10 KR KR1020157008264A patent/KR102148679B1/ko active Active
- 2013-11-10 JP JP2015541973A patent/JP6268183B2/ja active Active
- 2013-11-10 SG SG11201502725TA patent/SG11201502725TA/en unknown
- 2013-11-10 AU AU2013345107A patent/AU2013345107B2/en active Active
- 2013-11-10 US US14/076,256 patent/US9926324B2/en active Active
- 2013-11-10 EP EP13855522.2A patent/EP2919784B1/en active Active
- 2013-11-10 BR BR112015006726-3A patent/BR112015006726B1/pt not_active IP Right Cessation
- 2013-11-10 CN CN201380054625.XA patent/CN104755085B/zh active Active
-
2015
- 2015-04-16 ZA ZA2015/02575A patent/ZA201502575B/en unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011500823A (ja) | 2007-10-22 | 2011-01-06 | グラクソスミスクライン・リミテッド・ライアビリティ・カンパニー | Ｐｉ３キナーゼ阻害物質としてのピリドスルホンアミド誘導体 |
Non-Patent Citations (3)
| Title |
|---|
| Bioorganic & Medicinal Chemistry Letters, Vol.21, pp.6977-6981 (2011)* |
| J. Med. Chem., vol.54, pp.5174-5184 (2011)* |
| Journal of Medicinal Chemistry, Vol.54, pp.2455-2466 (2011)* |
Also Published As
| Publication number | Publication date |
|---|---|
| SG11201502725TA (en) | 2015-05-28 |
| RU2665036C9 (ru) | 2018-11-12 |
| US20140134133A1 (en) | 2014-05-15 |
| KR20150083833A (ko) | 2015-07-20 |
| AU2013345107B2 (en) | 2016-02-25 |
| EP3299019A1 (en) | 2018-03-28 |
| AU2013345107A1 (en) | 2015-04-30 |
| TWI574962B (zh) | 2017-03-21 |
| BR112015006726A2 (pt) | 2017-08-22 |
| MY180641A (en) | 2020-12-04 |
| CA2889346C (en) | 2018-09-25 |
| JP2015536994A (ja) | 2015-12-24 |
| CA2889346A1 (en) | 2014-05-22 |
| RU2015116102A (ru) | 2017-01-10 |
| EP3299019B1 (en) | 2019-10-09 |
| HK1210956A1 (en) | 2016-05-13 |
| ES2661380T3 (es) | 2018-03-28 |
| WO2014078211A1 (en) | 2014-05-22 |
| EP2919784A1 (en) | 2015-09-23 |
| EP2919784A4 (en) | 2016-07-06 |
| JP6268183B2 (ja) | 2018-01-24 |
| TW201422615A (zh) | 2014-06-16 |
| EP2919784B1 (en) | 2017-12-20 |
| RU2665036C2 (ru) | 2018-08-27 |
| CN104755085B (zh) | 2018-05-01 |
| US9926324B2 (en) | 2018-03-27 |
| BR112015006726B1 (pt) | 2021-11-23 |
| CN104755085A (zh) | 2015-07-01 |
| ZA201502575B (en) | 2016-11-30 |
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