JP2016527277A5 - - Google Patents
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- JP2016527277A5 JP2016527277A5 JP2016531936A JP2016531936A JP2016527277A5 JP 2016527277 A5 JP2016527277 A5 JP 2016527277A5 JP 2016531936 A JP2016531936 A JP 2016531936A JP 2016531936 A JP2016531936 A JP 2016531936A JP 2016527277 A5 JP2016527277 A5 JP 2016527277A5
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- Prior art keywords
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- 150000001875 compounds Chemical class 0.000 claims 54
- 229910052739 hydrogen Inorganic materials 0.000 claims 31
- 239000001257 hydrogen Substances 0.000 claims 31
- 150000002431 hydrogen Chemical class 0.000 claims 25
- 125000000217 alkyl group Chemical group 0.000 claims 17
- 150000003839 salts Chemical class 0.000 claims 10
- 125000001475 halogen functional group Chemical group 0.000 claims 9
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 claims 8
- -1 methyl aspartate Chemical compound 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 239000004471 Glycine Substances 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 229960003080 taurine Drugs 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- YIQPUJZXAGQSKG-VKHMYHEASA-N (2r)-2-amino-2-chloropropanoic acid Chemical compound C[C@@](N)(Cl)C(O)=O YIQPUJZXAGQSKG-VKHMYHEASA-N 0.000 claims 2
- YARNOIDQQUOOES-VKHMYHEASA-N (2r)-2-amino-2-fluoropropanoic acid Chemical compound C[C@@](N)(F)C(O)=O YARNOIDQQUOOES-VKHMYHEASA-N 0.000 claims 2
- MVMQEZPNWYPJIX-VKHMYHEASA-N (2r)-2-amino-2-iodopropanoic acid Chemical compound C[C@@](N)(I)C(O)=O MVMQEZPNWYPJIX-VKHMYHEASA-N 0.000 claims 2
- ORQLXCMGAMWKMJ-REOHCLBHSA-N (2r)-2-amino-3-bromopropanoic acid Chemical compound BrC[C@H](N)C(O)=O ORQLXCMGAMWKMJ-REOHCLBHSA-N 0.000 claims 2
- DIZAJUVUZKMLQL-REOHCLBHSA-N (2r)-2-amino-3-iodopropanoic acid Chemical compound IC[C@H](N)C(O)=O DIZAJUVUZKMLQL-REOHCLBHSA-N 0.000 claims 2
- PEMUHKUIQHFMTH-QMMMGPOBSA-N (2s)-2-amino-3-(4-bromophenyl)propanoic acid Chemical compound OC(=O)[C@@H](N)CC1=CC=C(Br)C=C1 PEMUHKUIQHFMTH-QMMMGPOBSA-N 0.000 claims 2
- ASBJGPTTYPEMLP-UHFFFAOYSA-N 3-chloroalanine Chemical compound ClCC(N)C(O)=O ASBJGPTTYPEMLP-UHFFFAOYSA-N 0.000 claims 2
- XWHHYOYVRVGJJY-QMMMGPOBSA-N 4-fluoro-L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(F)C=C1 XWHHYOYVRVGJJY-QMMMGPOBSA-N 0.000 claims 2
- PZNQZSRPDOEBMS-QMMMGPOBSA-N 4-iodo-L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(I)C=C1 PZNQZSRPDOEBMS-QMMMGPOBSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- NIGWMJHCCYYCSF-UHFFFAOYSA-N Fenclonine Chemical compound OC(=O)C(N)CC1=CC=C(Cl)C=C1 NIGWMJHCCYYCSF-UHFFFAOYSA-N 0.000 claims 2
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims 2
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 2
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims 2
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims 2
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 2
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims 2
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 2
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 2
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- CWLQUGTUXBXTLF-UHFFFAOYSA-N N-methyl-L-proline monohydrate Natural products CN1CCCC1C(O)=O CWLQUGTUXBXTLF-UHFFFAOYSA-N 0.000 claims 2
- CWLQUGTUXBXTLF-YFKPBYRVSA-N N-methylproline Chemical compound CN1CCC[C@H]1C(O)=O CWLQUGTUXBXTLF-YFKPBYRVSA-N 0.000 claims 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 2
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims 2
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims 2
- 235000004279 alanine Nutrition 0.000 claims 2
- 229940009098 aspartate Drugs 0.000 claims 2
- 235000003704 aspartic acid Nutrition 0.000 claims 2
- 229940000635 beta-alanine Drugs 0.000 claims 2
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- YEJSPQZHMWGIGP-UHFFFAOYSA-N dl-glutamic acid dimethyl ester Natural products COC(=O)CCC(N)C(=O)OC YEJSPQZHMWGIGP-UHFFFAOYSA-N 0.000 claims 2
- 235000013922 glutamic acid Nutrition 0.000 claims 2
- 239000004220 glutamic acid Substances 0.000 claims 2
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims 2
- 229960000310 isoleucine Drugs 0.000 claims 2
- 229930182817 methionine Natural products 0.000 claims 2
- SEWIYICDCVPBEW-UHFFFAOYSA-N methyl glutamate Chemical compound COC(=O)C(N)CCC(O)=O SEWIYICDCVPBEW-UHFFFAOYSA-N 0.000 claims 2
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims 2
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims 2
- 229910052711 selenium Inorganic materials 0.000 claims 2
- 230000002194 synthesizing effect Effects 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims 2
- 239000004474 valine Substances 0.000 claims 2
- 208000022309 Alcoholic Liver disease Diseases 0.000 claims 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 1
- 206010022489 Insulin Resistance Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361861109P | 2013-08-01 | 2013-08-01 | |
| US61/861,109 | 2013-08-01 | ||
| US201462004436P | 2014-05-29 | 2014-05-29 | |
| US62/004,436 | 2014-05-29 | ||
| PCT/US2014/049460 WO2015017813A2 (en) | 2013-08-01 | 2014-08-01 | Inhibitors of the farnesoid x receptor and uses in medicine |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016527277A JP2016527277A (ja) | 2016-09-08 |
| JP2016527277A5 true JP2016527277A5 (https=) | 2017-09-07 |
| JP6556129B2 JP6556129B2 (ja) | 2019-08-07 |
Family
ID=51358096
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016531936A Expired - Fee Related JP6556129B2 (ja) | 2013-08-01 | 2014-08-01 | ファルネソイドｘ受容体の阻害剤及び医薬としての使用 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US9540415B2 (https=) |
| EP (1) | EP3027637B1 (https=) |
| JP (1) | JP6556129B2 (https=) |
| CN (2) | CN105593237B (https=) |
| AU (1) | AU2014296023B2 (https=) |
| BR (1) | BR112016002268B1 (https=) |
| CA (1) | CA2920017C (https=) |
| NZ (1) | NZ716568A (https=) |
| WO (1) | WO2015017813A2 (https=) |
Families Citing this family (25)
| 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 |
| SMT202000070T1 (it) * | 2014-05-29 | 2020-03-13 | Bar Pharmaceuticals S R L | Derivati del colano per l'uso del trattamento e/o la prevenzione di malattie mediate da fxr e tgr5/gpbar1 |
| SG11201703717SA (en) | 2014-11-06 | 2017-06-29 | Enanta Pharm Inc | Bile acid analogs an fxr/tgr5 agonists and methods of use thereof |
| EP3223823A4 (en) | 2014-11-26 | 2018-10-17 | Enanta Pharmaceuticals, Inc. | Bile acid analogs as fxr/tgr5 agonists and methods of use thereof |
| US10208081B2 (en) | 2014-11-26 | 2019-02-19 | Enanta Pharmaceuticals, Inc. | Bile acid derivatives as FXR/TGR5 agonists and methods of use thereof |
| US11578097B2 (en) | 2014-11-26 | 2023-02-14 | Enanta Pharmaceuticals, Inc. | Tetrazole derivatives of bile acids as FXR/TGR5 agonists and methods of use thereof |
| EP3256134A4 (en) | 2015-02-11 | 2018-10-03 | Enanta Pharmaceuticals, Inc. | Bile acid analogs as fxr/tgr5 agonists and methods of use thereof |
| WO2016161003A1 (en) | 2015-03-31 | 2016-10-06 | Enanta Phamraceuticals, Inc. | Bile acid derivatives as fxr/tgr5 agonists and methods of use thereof |
| JP2018519246A (ja) * | 2015-04-28 | 2018-07-19 | ジエンス ハンセン ファーマセウティカル グループ カンパニー リミテッド | コール酸誘導体、及びその製造方法及び医薬用途 |
| US10323060B2 (en) | 2016-02-23 | 2019-06-18 | Enanta Pharmaceuticals, Inc. | Benzoic acid derivatives of bile acid as FXR/TGR5 agonists and methods of use thereof |
| CA3252823A1 (en) | 2016-06-13 | 2025-02-25 | Gilead Sciences, Inc. | Substituted tert-butyl-3-(2-chloro-phenyl)-3-hydroxyazetidine-1-carboxylate compounds |
| MX385718B (es) | 2016-06-13 | 2025-03-18 | Gilead Sciences Inc | Compuestos moduladores de fxr (nr1h4). |
| IT201600068742A1 (it) * | 2016-07-01 | 2018-01-01 | Bar Pharmaceuticals Soc A Responsabilita Limitata | Derivati dell'acido iodesossicolico e loro uso |
| CN106237332A (zh) * | 2016-08-11 | 2016-12-21 | 河南大学 | 核受体fxr在肝癌干细胞靶向治疗中的应用 |
| CN110121347A (zh) | 2016-11-29 | 2019-08-13 | 英安塔制药有限公司 | 制备磺酰脲胆汁酸衍生物的方法 |
| US10472386B2 (en) | 2017-02-14 | 2019-11-12 | Enanta Pharmaceuticals, Inc. | Bile acid derivatives as FXR agonists and methods of use thereof |
| PT3600309T (pt) | 2017-03-28 | 2022-10-03 | Gilead Sciences Inc | Combinações terapêuticas para o tratamento de doenças hepáticas |
| BR112019020780A2 (pt) | 2017-04-07 | 2020-04-28 | Enanta Pharm Inc | processo para preparação de derivados de ácido biliar de carbamato de sulfonila |
| US11028111B2 (en) | 2017-12-19 | 2021-06-08 | Xi' An Biocare Pharma Ltd. | Compound for treating metabolic diseases and preparation method and use thereof |
| IT201800005598A1 (it) | 2018-05-22 | 2019-11-22 | Ossadiazoli come antagonisti del recettore fxr | |
| EP3911647B1 (en) | 2019-01-15 | 2023-12-13 | Gilead Sciences, Inc. | Isoxazole compound as fxr agonist and pharmaceutical compositions comprising same |
| CA3233305A1 (en) | 2019-02-19 | 2020-08-27 | Gilead Sciences, Inc. | Solid forms of fxr agonists |
| CN112409435B (zh) * | 2019-08-23 | 2023-07-18 | 深圳云合医药科技合伙企业(有限合伙) | 胆汁酸衍生物及其组合物和应用 |
| US20220378766A1 (en) * | 2021-05-25 | 2022-12-01 | Louis Habash | Modulating expression level of a gene encoding an uncoupling protein by treating a human subject with a nitroxide |
| US20230128120A1 (en) * | 2021-10-21 | 2023-04-27 | University Of Washington | Omega muricholic acid as a pregnane x receptor ligand for treating hepato-intestinal diseases |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4235871A (en) | 1978-02-24 | 1980-11-25 | Papahadjopoulos Demetrios P | Method of encapsulating biologically active materials in lipid vesicles |
| US4501728A (en) | 1983-01-06 | 1985-02-26 | Technology Unlimited, Inc. | Masking of liposomes from RES recognition |
| US5019369A (en) | 1984-10-22 | 1991-05-28 | Vestar, Inc. | Method of targeting tumors in humans |
| WO1987002367A2 (en) | 1985-10-18 | 1987-04-23 | The Upjohn Company | Cyclic hydrocarbons with an aminoalkyl sidechain |
| US4837028A (en) | 1986-12-24 | 1989-06-06 | Liposome Technology, Inc. | Liposomes with enhanced circulation time |
| IT1222395B (it) * | 1987-07-30 | 1990-09-05 | Pierrel Spa | Composizione farmaceutica per somministrazione intranasale comprendente l'ormone ghrh,un agonista colinergico e/o un sale biliare |
| IT1219733B (it) * | 1988-06-28 | 1990-05-24 | Istituto Chemioterapico Di Lod | Derivato dell' acido ursodesossicolico |
| JPH0637392B2 (ja) * | 1988-11-25 | 1994-05-18 | 健二 片桐 | 胆汁うっ滞改善剤 |
| IT1229570B (it) | 1989-04-17 | 1991-09-04 | Giuliani Spa | Derivati fluorurati di acidi biliari, loro preparazione e composizioni farmaceutiche che li contengono. |
| IT1264131B1 (it) * | 1993-04-16 | 1996-09-16 | D R Drug Research Srl | Derivato dell'acido iodesossicolico |
| US6551623B1 (en) * | 1993-09-09 | 2003-04-22 | Lorus Therapeutics Inc. | Immunomodulating compositions from bile |
| GB9320597D0 (en) * | 1993-10-06 | 1993-11-24 | Proteus Molecular Design | Improvements in and realting to vaccines |
| IT1299270B1 (it) * | 1998-05-15 | 2000-02-29 | Moreno Paolini | Acidi biliari come induttori del sistema citocromo p450-dipendente, in particolare ad attivita' anticolestatica |
| DE69940958D1 (de) | 1998-12-23 | 2009-07-16 | Glaxo Group Ltd | Bestimmungsmethode fur liganden der nuklearen rezeptoren |
| US20020132223A1 (en) * | 1999-03-26 | 2002-09-19 | City Of Hope | Methods for modulating activity of the FXR nuclear receptor |
| WO2002094865A1 (en) * | 2001-05-24 | 2002-11-28 | Smithkline Beecham Corporation | Nonhuman pregnane x receptor sequences for use in comparative pharmacology |
| US7595311B2 (en) | 2002-05-24 | 2009-09-29 | Exelixis, Inc. | Azepinoindole derivatives as pharmaceutical agents |
| JP2008509912A (ja) | 2004-08-10 | 2008-04-03 | エグゼリクシス， インコーポレイテッド | 医薬品としての複素環化合物 |
| CN101395170A (zh) * | 2006-02-14 | 2009-03-25 | 英特塞普特药品公司 | 用于预防或治疗fxr介导的疾病或状态的作为fxr配体的胆汁酸衍生物 |
| US7932244B2 (en) * | 2006-06-27 | 2011-04-26 | Intercept Pharmaceuticals, Inc. | Bile acid derivatives as FXR ligands for the prevention or treatment of FXR-mediated diseases or conditions |
| WO2011022838A1 (en) | 2009-08-25 | 2011-03-03 | British Columbia Cancer Agency Branch | Polyhydroxylated bile acids for treatment of biliary disorders |
| US20110071100A1 (en) * | 2008-05-05 | 2011-03-24 | Tiltan Pharma Ltd. | Sulfobetaines for cancer, obesity, macular degeneration, neurodegenerative diseases |
| WO2010014836A2 (en) | 2008-07-30 | 2010-02-04 | Intercept Pharmaceuticals, Inc. | Tgr5 modulators and methods of use thereof |
| CN101891791B (zh) * | 2009-05-22 | 2012-10-03 | 中国科学院上海应用物理研究所 | 一种标记胆汁酸衍生物及其参照化合物、制备方法和应用 |
-
2014
- 2014-08-01 BR BR112016002268-8A patent/BR112016002268B1/pt not_active IP Right Cessation
- 2014-08-01 CN CN201480054322.2A patent/CN105593237B/zh not_active Expired - Fee Related
- 2014-08-01 WO PCT/US2014/049460 patent/WO2015017813A2/en not_active Ceased
- 2014-08-01 AU AU2014296023A patent/AU2014296023B2/en not_active Ceased
- 2014-08-01 US US14/909,263 patent/US9540415B2/en not_active Expired - Fee Related
- 2014-08-01 EP EP14752716.2A patent/EP3027637B1/en active Active
- 2014-08-01 JP JP2016531936A patent/JP6556129B2/ja not_active Expired - Fee Related
- 2014-08-01 CN CN201910393592.0A patent/CN110437297B9/zh not_active Expired - Fee Related
- 2014-08-01 CA CA2920017A patent/CA2920017C/en active Active
- 2014-08-01 NZ NZ716568A patent/NZ716568A/en not_active IP Right Cessation
-
2016
- 2016-12-06 US US15/371,032 patent/US10233209B2/en active Active
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