UA111827C2 - Спосіб отримання інгенол-3-ангелату - Google Patents
Спосіб отримання інгенол-3-ангелатуInfo
- Publication number
- UA111827C2 UA111827C2 UAA201302103A UAA201302103A UA111827C2 UA 111827 C2 UA111827 C2 UA 111827C2 UA A201302103 A UAA201302103 A UA A201302103A UA A201302103 A UAA201302103 A UA A201302103A UA 111827 C2 UA111827 C2 UA 111827C2
- Authority
- UA
- Ukraine
- Prior art keywords
- angelate
- inhenol
- obtaining
- ingenol
- methods
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 3
- VEBVPUXQAPLADL-UHFFFAOYSA-N Ingenol Natural products C1=C(CO)C(O)C2(O)C(O)C(C)=CC32C(C)CC2C(C)(C)C2C1C3=O VEBVPUXQAPLADL-UHFFFAOYSA-N 0.000 abstract 2
- VDJHFHXMUKFKET-UHFFFAOYSA-N Ingenol mebutate Natural products CC1CC2C(C)(C)C2C2C=C(CO)C(O)C3(O)C(OC(=O)C(C)=CC)C(C)=CC31C2=O VDJHFHXMUKFKET-UHFFFAOYSA-N 0.000 abstract 2
- VEBVPUXQAPLADL-POYOOMFHSA-N ingenol Chemical compound C1=C(CO)[C@@H](O)[C@]2(O)[C@@H](O)C(C)=C[C@]32[C@H](C)C[C@H]2C(C)(C)[C@H]2[C@H]1C3=O VEBVPUXQAPLADL-POYOOMFHSA-N 0.000 abstract 2
- VDJHFHXMUKFKET-WDUFCVPESA-N ingenol mebutate Chemical compound C[C@@H]1C[C@H]2C(C)(C)[C@H]2[C@@H]2C=C(CO)[C@@H](O)[C@]3(O)[C@@H](OC(=O)C(\C)=C/C)C(C)=C[C@]31C2=O VDJHFHXMUKFKET-WDUFCVPESA-N 0.000 abstract 2
- 229960002993 ingenol mebutate Drugs 0.000 abstract 2
- 239000000543 intermediate Substances 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
- C07C251/88—Hydrazones having also the other nitrogen atom doubly-bound to a carbon atom, e.g. azines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/567—Preparation of carboxylic acid anhydrides by reactions not involving carboxylic acid anhydride groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/297—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/70—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with ring systems containing two or more relevant rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/08—1,3-Dioxanes; Hydrogenated 1,3-dioxanes condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/188—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/86—Ring systems containing bridged rings containing four rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/93—Spiro compounds
- C07C2603/95—Spiro compounds containing "not free" spiro atoms
- C07C2603/98—Spiro compounds containing "not free" spiro atoms containing at least one ring with more than six ring members
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Даний винахід стосується способів отримання інгенол-3-ангелату (І) з інгенолу (II). Крім того, винахід стосується проміжних продуктів, застосовних для синтезу інгенол-3-ангелату (І) з інгенолу (II), і способів отримання вказаних проміжних продуктів.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36601810P | 2010-07-20 | 2010-07-20 | |
| PCT/DK2011/000081 WO2012010172A1 (en) | 2010-07-20 | 2011-07-08 | A method of producing ingenol-3-angelate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA111827C2 true UA111827C2 (uk) | 2016-06-24 |
Family
ID=44503402
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UAA201302103A UA111827C2 (uk) | 2010-07-20 | 2011-08-07 | Спосіб отримання інгенол-3-ангелату |
Country Status (28)
| Country | Link |
|---|---|
| US (3) | US8901356B2 (uk) |
| EP (2) | EP2595948B1 (uk) |
| JP (1) | JP5816279B2 (uk) |
| KR (1) | KR101914460B1 (uk) |
| CN (2) | CN103119016A (uk) |
| AU (1) | AU2011282028B2 (uk) |
| BR (1) | BR112013001245B1 (uk) |
| CA (1) | CA2805965A1 (uk) |
| CY (1) | CY1122350T1 (uk) |
| DK (1) | DK2595948T3 (uk) |
| ES (1) | ES2753998T3 (uk) |
| HR (1) | HRP20192000T1 (uk) |
| HU (1) | HUE046240T2 (uk) |
| IL (3) | IL223718A (uk) |
| LT (1) | LT2595948T (uk) |
| MX (1) | MX2013000429A (uk) |
| MY (1) | MY163339A (uk) |
| NZ (1) | NZ606720A (uk) |
| PL (1) | PL2595948T3 (uk) |
| PT (1) | PT2595948T (uk) |
| RS (1) | RS59532B1 (uk) |
| RU (1) | RU2586975C2 (uk) |
| SG (1) | SG186750A1 (uk) |
| SI (1) | SI2595948T1 (uk) |
| TW (1) | TWI525075B (uk) |
| UA (1) | UA111827C2 (uk) |
| WO (1) | WO2012010172A1 (uk) |
| ZA (1) | ZA201300142B (uk) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0525680D0 (en) | 2005-12-16 | 2006-01-25 | Peplin Ltd | Therapeutic compositions |
| WO2012010172A1 (en) | 2010-07-20 | 2012-01-26 | Leo Pharma A/S | A method of producing ingenol-3-angelate |
| JP2014507396A (ja) * | 2010-12-22 | 2014-03-27 | レオ・ラボラトリーズ・リミテッド | イノゲノール−３−アシラートｉ |
| IN2014DN06738A (uk) | 2012-01-25 | 2015-05-22 | Leo Pharma As | |
| EP2872477B1 (en) * | 2012-07-16 | 2018-09-05 | Leo Laboratories Limited | Process for the preparation of ingenol-3-angelate from 20-deoxy-ingenol |
| CN103483193A (zh) * | 2013-09-10 | 2014-01-01 | 南京奇鹤医药科技有限公司 | 一种巨大戟醇甲基丁烯酸酯的制备方法 |
| WO2015176175A1 (en) * | 2014-05-23 | 2015-11-26 | Alphora Research Inc. | A continuous flow process for the preparation of ingenol-3-mebutate |
| CN104649901B (zh) * | 2015-02-09 | 2017-03-29 | 中国科学院昆明植物研究所 | 一种治疗光化性角化病的原料药物巨大戟醇甲基丁烯酸酯的制备方法 |
| WO2016191836A1 (pt) * | 2015-06-03 | 2016-12-08 | Amazônia Fitomedicamentos Ltda. | Método de preparação de ingenol-3-dodecanoato, método de preparação de 3-etinil-3-hidroxi-4.7.7-trimetilbiciclo[4.1.0]heptano-2-carbaldeído e método de preparação de 2,2-dimetil-4-etinil-5-trifenilfosforanilideno-1,3-dioxano |
| WO2016191835A1 (pt) * | 2015-06-03 | 2016-12-08 | Amazônia Fitomedicamentos Ltda. | Método de preparação de ingenol-5,20-acetonida, método de preparação de 3-etinil-3-hidroxi-4.7.7-trimetilbiciclo[4.1.0] heptano-2-carbaldeído, método de preparação do composto 2,2-dimetil-4-etinil-5 -trifenilfosforanilideno-1,3-dioxano e composto intermediário |
| WO2016191837A1 (pt) * | 2015-06-03 | 2016-12-08 | Amazônia Fitomedicamentos Ltda. | Método de preparação de ingenol-3-hexanoato, método de preparação de 3-etinil-3-hidroxi-4.7.7-trimetilbiciclo[4.1.0]heptano-2-carbaldeído e método de preparação do composto 2,2-dimetil-4-etinil-5-trifenilfosforanilideno-1,3-dioxano |
| WO2017108927A1 (en) * | 2015-12-22 | 2017-06-29 | Leo Laboratories Limited | Process for preparation of ingenol 3-(3.5-diethylisoxazole-4-carboxylate) |
| WO2017156350A1 (en) | 2016-03-09 | 2017-09-14 | K-Gen, Inc. | Methods of cancer treatment |
| AU2018280534B2 (en) * | 2017-06-09 | 2021-04-01 | Tianjin Pharmaceutical Da Ren Tang Group Corp., Ltd. Traditional Chinese Medicine Research Institute | 13-oxidized ingenol derivative and use thereof |
| US20240132460A1 (en) * | 2021-03-10 | 2024-04-25 | The Board Of Trustees Of The Leland Stanford Junior University | Synthesis of tigilanol tiglate and analogs thereof |
| CN113336628B (zh) * | 2021-04-16 | 2023-02-10 | 云南省中医中药研究院 | 一种二醇蔷薇烷、其制备方法及用途 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5920247A (ja) * | 1982-07-28 | 1984-02-01 | Taiyo Koryo Kk | アンゲリカ酸不飽和エステル類及びその香料組成物 |
| JPS6036479A (ja) * | 1983-08-08 | 1985-02-25 | Kotobuki Seiyaku Kk | １，３−ジオキサン誘導体、本化合物を有効成分とする抗潰瘍剤及びその製造方法 |
| JP3773578B2 (ja) * | 1996-02-29 | 2006-05-10 | 三共株式会社 | タキソール合成中間体 |
| AUPQ801700A0 (en) | 2000-06-07 | 2000-06-29 | Peplin Research Pty Ltd | Enzyme and viral activation |
| AUPQ923100A0 (en) * | 2000-08-07 | 2000-08-31 | Peplin Research Pty Ltd | Treatment of prostate cancer |
| US8022103B2 (en) * | 2005-07-13 | 2011-09-20 | Salvia Sciences, Inc. | Ester prodrugs of prostratin and related phorbol compounds |
| CA2541903A1 (en) * | 2006-04-20 | 2007-10-20 | Peplin Research Pty. Ltd. | A method of diagnosis and treatment |
| JP4952208B2 (ja) | 2006-11-16 | 2012-06-13 | 株式会社ツムラ | プラエルプトリンａの製造方法 |
| RS56337B1 (sr) * | 2010-04-16 | 2017-12-29 | Leo Pharma As | Ortorombični kristalni ingenol mebutat |
| WO2012010172A1 (en) | 2010-07-20 | 2012-01-26 | Leo Pharma A/S | A method of producing ingenol-3-angelate |
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2011
- 2011-07-08 WO PCT/DK2011/000081 patent/WO2012010172A1/en active Application Filing
- 2011-07-08 BR BR112013001245-5A patent/BR112013001245B1/pt not_active IP Right Cessation
- 2011-07-08 CN CN2011800355785A patent/CN103119016A/zh active Pending
- 2011-07-08 MX MX2013000429A patent/MX2013000429A/es active IP Right Grant
- 2011-07-08 DK DK11738152.5T patent/DK2595948T3/da active
- 2011-07-08 JP JP2013519965A patent/JP5816279B2/ja not_active Expired - Fee Related
- 2011-07-08 EP EP11738152.5A patent/EP2595948B1/en active Active
- 2011-07-08 EP EP19193104.7A patent/EP3640236A1/en not_active Withdrawn
- 2011-07-08 CN CN201611161194.9A patent/CN107011167A/zh active Pending
- 2011-07-08 MY MYPI2013000200A patent/MY163339A/en unknown
- 2011-07-08 RS RS20191401A patent/RS59532B1/sr unknown
- 2011-07-08 US US13/811,207 patent/US8901356B2/en active Active
- 2011-07-08 NZ NZ606720A patent/NZ606720A/en not_active IP Right Cessation
- 2011-07-08 RU RU2013107386/04A patent/RU2586975C2/ru active
- 2011-07-08 SG SG2012093084A patent/SG186750A1/en unknown
- 2011-07-08 SI SI201131791T patent/SI2595948T1/sl unknown
- 2011-07-08 AU AU2011282028A patent/AU2011282028B2/en not_active Ceased
- 2011-07-08 ES ES11738152T patent/ES2753998T3/es active Active
- 2011-07-08 PL PL11738152T patent/PL2595948T3/pl unknown
- 2011-07-08 HU HUE11738152A patent/HUE046240T2/hu unknown
- 2011-07-08 CA CA2805965A patent/CA2805965A1/en not_active Abandoned
- 2011-07-08 KR KR1020137004205A patent/KR101914460B1/ko active IP Right Grant
- 2011-07-08 PT PT117381525T patent/PT2595948T/pt unknown
- 2011-07-08 LT LT11738152T patent/LT2595948T/lt unknown
- 2011-07-19 TW TW100125495A patent/TWI525075B/zh not_active IP Right Cessation
- 2011-08-07 UA UAA201302103A patent/UA111827C2/uk unknown
-
2012
- 2012-12-18 IL IL223718A patent/IL223718A/en active IP Right Grant
-
2013
- 2013-01-07 ZA ZA2013/00142A patent/ZA201300142B/en unknown
-
2014
- 2014-12-01 US US14/557,302 patent/US9416084B2/en not_active Expired - Fee Related
-
2016
- 2016-06-09 US US15/178,112 patent/US9676698B2/en active Active
- 2016-10-06 IL IL248217A patent/IL248217B/en active IP Right Grant
-
2017
- 2017-12-24 IL IL256533A patent/IL256533B/en active IP Right Grant
-
2019
- 2019-11-05 HR HRP20192000TT patent/HRP20192000T1/hr unknown
- 2019-11-21 CY CY20191101224T patent/CY1122350T1/el unknown
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