JP7248209B2 - 3’-デオキシアデノシン-5’-o-[フェニル(ベンジルオシキ-l-アラニニル)]ホスフェート(nuc-7738)の合成 - Google Patents

3’-デオキシアデノシン-5’-o-[フェニル(ベンジルオシキ-l-アラニニル)]ホスフェート(nuc-7738)の合成 Download PDF

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JP7248209B2
JP7248209B2 JP2019569336A JP2019569336A JP7248209B2 JP 7248209 B2 JP7248209 B2 JP 7248209B2 JP 2019569336 A JP2019569336 A JP 2019569336A JP 2019569336 A JP2019569336 A JP 2019569336A JP 7248209 B2 JP7248209 B2 JP 7248209B2
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JP2020523381A (ja
JP2020523381A5 (enExample
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ラクシュミー ナラシンハ ラーオ ダムマラパテ ヴェンカタ
ブスハン コタラ マニ
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ニューカナ パブリック リミテッド カンパニー
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/16—Purine radicals
    • C07H19/20—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C07H1/02—Phosphorylation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • C07H19/10—Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/16—Purine radicals
    • C07H19/20—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
    • C07H19/207—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids the phosphoric or polyphosphoric acids being esterified by a further hydroxylic compound, e.g. flavine adenine dinucleotide or nicotinamide-adenine dinucleotide
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
JP2019569336A 2017-06-14 2018-06-14 3’-デオキシアデノシン-5’-o-[フェニル(ベンジルオシキ-l-アラニニル)]ホスフェート(nuc-7738)の合成 Active JP7248209B2 (ja)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB1709471.5 2017-06-14
GBGB1709471.5A GB201709471D0 (en) 2017-06-14 2017-06-14 Diastereoselective synthesis of hosphate derivatives
PCT/GB2018/051641 WO2018229495A1 (en) 2017-06-14 2018-06-14 Synthesis of 3'-deoxyadenosine-5'-0-[phenyl(benzyloxy-l-alaninyl)]phosphate (nuc-7738)

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JP2020523381A JP2020523381A (ja) 2020-08-06
JP2020523381A5 JP2020523381A5 (enExample) 2021-07-26
JP7248209B2 true JP7248209B2 (ja) 2023-03-29

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JP2019569336A Active JP7248209B2 (ja) 2017-06-14 2018-06-14 3’-デオキシアデノシン-5’-o-[フェニル(ベンジルオシキ-l-アラニニル)]ホスフェート(nuc-7738)の合成
JP2019569286A Active JP7279991B2 (ja) 2017-06-14 2018-06-14 ホスフェート誘導体の合成
JP2023076006A Active JP7525687B2 (ja) 2017-06-14 2023-05-02 ホスフェート誘導体の合成
JP2024114519A Pending JP2024138523A (ja) 2017-06-14 2024-07-18 ホスフェート誘導体の合成
JP2025266864A Pending JP2026034703A (ja) 2017-06-14 2025-12-19 ホスフェート誘導体の合成

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JP2019569286A Active JP7279991B2 (ja) 2017-06-14 2018-06-14 ホスフェート誘導体の合成
JP2023076006A Active JP7525687B2 (ja) 2017-06-14 2023-05-02 ホスフェート誘導体の合成
JP2024114519A Pending JP2024138523A (ja) 2017-06-14 2024-07-18 ホスフェート誘導体の合成
JP2025266864A Pending JP2026034703A (ja) 2017-06-14 2025-12-19 ホスフェート誘導体の合成

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US (4) US11897913B2 (enExample)
EP (3) EP3638684B1 (enExample)
JP (5) JP7248209B2 (enExample)
KR (2) KR102695300B1 (enExample)
CN (3) CN117486959A (enExample)
AU (3) AU2018284131B2 (enExample)
BR (1) BR112019026747A2 (enExample)
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CL (1) CL2019003632A1 (enExample)
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GB (1) GB201709471D0 (enExample)
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MA (1) MA49379A (enExample)
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NZ (2) NZ759692A (enExample)
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2023095954A (ja) * 2017-06-14 2023-07-06 ニューカナ パブリック リミテッド カンパニー ホスフェート誘導体の合成

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2569185T3 (es) 2011-03-01 2016-05-09 Nucana Biomed Limited Derivados de fosforamidato de 5-fluoro-2'-desoxiuridina para uso en el tratamiento del cáncer
EA033046B1 (ru) 2014-06-25 2019-08-30 НУКАНА ПиЭлСи Состав, содержащий пролекарство гемцитабина
HRP20191461T1 (hr) 2014-11-28 2019-11-15 NuCana plc Novi 2' i/ili 5' derivati 3'-deoksi adenozina supstituirani aminokiselinskim esterom fosforamidata, kao antikancerogenog spoja
CA3007347C (en) 2015-12-11 2020-08-04 NuCana plc Diastereoselective synthesis of phosphate derivatives and of the gemcitabine prodrug nuc-1031
GB201522764D0 (en) 2015-12-23 2016-02-03 Nucana Biomed Ltd Formulations of phosphate derivatives
GB201609600D0 (en) 2016-06-01 2016-07-13 Nucuna Biomed Ltd Cancer treatments
GB201715011D0 (en) 2017-09-18 2017-11-01 Nucana Biomed Ltd Floxuridine synthesis
CN112409421A (zh) * 2020-12-01 2021-02-26 上海兆维科技发展有限公司 一种3’-磷酸酯核苷的制备方法
KR20250012582A (ko) 2022-05-12 2025-01-24 뉴카나 피엘씨 암 치료
CN120584123A (zh) 2022-12-07 2025-09-02 努卡那有限公司 核苷衍生物nuc-3373的合成

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008533191A (ja) 2005-03-21 2008-08-21 ユニバーシティ、カレッジ、カーディフ、コンサルタンツ、リミテッド 癌の治療における使用のためのヌクレオシド化合物のホスホルアミデート誘導体
JP2020523378A (ja) 2017-06-14 2020-08-06 ニューカナ パブリック リミテッド カンパニー ホスフェート誘導体の合成

Family Cites Families (57)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE279248C (enExample)
US3792039A (en) 1971-12-27 1974-02-12 Miles Lab Poly 2'-fluoro-2'-deoxyuridylic acid
US4500707A (en) * 1980-02-29 1985-02-19 University Patents, Inc. Nucleosides useful in the preparation of polynucleotides
US4357324A (en) 1981-02-24 1982-11-02 The United States Of America As Represented By The Department Of Health And Human Services Prodrug derivatives of 9β-D-arabinofuranosyl-2-fluoroadenine
US4668777A (en) * 1981-03-27 1987-05-26 University Patents, Inc. Phosphoramidite nucleoside compounds
ES2172303T3 (es) 1998-01-23 2002-09-16 Newbiotics Inc Agentes terapeuticos obtenidos por catalisis enzimatica.
US7462605B2 (en) 1998-01-23 2008-12-09 Celmed Oncology (Usa), Inc. Phosphoramidate compounds and methods of use
US6683061B1 (en) 1999-07-22 2004-01-27 Newbiotics, Inc. Enzyme catalyzed therapeutic activation
GB0317009D0 (en) 2003-07-21 2003-08-27 Univ Cardiff Chemical compounds
EP1827460A4 (en) 2004-12-09 2012-03-14 Univ Minnesota NUCLEOSIDE WITH ANTIVIRAL AND ANTI-CANCER EFFECT
CN101287472B (zh) 2005-08-15 2011-10-12 弗·哈夫曼-拉罗切有限公司 抗病毒的4'-取代前核苷酸的氨基磷酸酯类化合物
GB0623493D0 (en) 2006-11-24 2007-01-03 Univ Cardiff Chemical compounds
US7951789B2 (en) * 2006-12-28 2011-05-31 Idenix Pharmaceuticals, Inc. Compounds and pharmaceutical compositions for the treatment of viral infections
US7964580B2 (en) 2007-03-30 2011-06-21 Pharmasset, Inc. Nucleoside phosphoramidate prodrugs
US20090206007A1 (en) 2008-02-20 2009-08-20 Air Products And Chemicals, Inc. Process and apparatus for upgrading coal using supercritical water
BRPI1004575A2 (pt) 2009-01-09 2016-04-05 Inhibitex Inc composto, composição farmacêutica, método de tratamento de infecções virais, método de separação dos diaestereômeros de fósforo
WO2010108140A1 (en) 2009-03-20 2010-09-23 Alios Biopharma, Inc. Substituted nucleoside and nucleotide analogs
TWI576352B (zh) 2009-05-20 2017-04-01 基利法瑪席特有限責任公司 核苷磷醯胺
US8618076B2 (en) 2009-05-20 2013-12-31 Gilead Pharmasset Llc Nucleoside phosphoramidates
AP2012006535A0 (en) 2010-03-31 2012-10-31 Gilead Pharmasset Llc Stereoselective synthesis of phosphorous containing actives
TW201136945A (en) 2010-03-31 2011-11-01 Pharmasset Inc Purine nucleoside phosphoramidate
EA025311B1 (ru) 2010-07-19 2016-12-30 Гайлид Сайэнсиз, Инк. Способы получения диастереомерно чистых фосфорамидатных пролекарств
WO2012040127A1 (en) 2010-09-22 2012-03-29 Alios Biopharma, Inc. Substituted nucleotide analogs
US20120070411A1 (en) 2010-09-22 2012-03-22 Alios Biopharma, Inc. Substituted nucleotide analogs
ES2716158T3 (es) 2010-11-30 2019-06-10 Gilead Pharmasset Llc 2'-spiro-nucleótidos para el tratamiento de hepatitis C
US8772474B2 (en) 2010-12-22 2014-07-08 Alios Biopharma, Inc. Cyclic nucleotide analogs
ES2569185T3 (es) 2011-03-01 2016-05-09 Nucana Biomed Limited Derivados de fosforamidato de 5-fluoro-2'-desoxiuridina para uso en el tratamiento del cáncer
US9556216B2 (en) * 2012-08-31 2017-01-31 Novartis Ag 2′-Ethynyl nucleoside derivatives for treatment of viral infections
AU2013346515B2 (en) 2012-11-16 2017-05-25 NuCana plc Process for preparing nucleoside prodrugs
ES2952714T3 (es) 2013-06-26 2023-11-03 Janssen Pharmaceuticals Inc Nucleósidos sustituidos, nucleótidos y análogos de los mismos
TW201542581A (zh) 2013-09-11 2015-11-16 艾默理大學 核苷酸與核苷治療組成物及其相關用途
CN105829333A (zh) 2013-10-11 2016-08-03 艾丽奥斯生物制药有限公司 取代的核苷、核苷酸及其类似物
JP2017504572A (ja) 2013-11-27 2017-02-09 アイデニクス・ファーマシューティカルズ・エルエルシー 肝臓癌治療のためのヌクレオチド類
CZ307789B6 (cs) 2014-04-15 2019-05-09 Zentiva, K.S. Způsob výroby biologicky účinných fosforamidátových léčiv
EP3131914B1 (en) * 2014-04-16 2023-05-10 Idenix Pharmaceuticals LLC 3'-substituted methyl or alkynyl nucleosides for the treatment of hcv
EA033046B1 (ru) 2014-06-25 2019-08-30 НУКАНА ПиЭлСи Состав, содержащий пролекарство гемцитабина
RS60968B1 (sr) 2014-06-25 2020-11-30 NuCana plc Prolekovi gemcitabina
US9834577B2 (en) 2014-07-22 2017-12-05 Laurus Labs Limited Process for the preparation of gemcitabine-[phenyl(benzoxy-L-alaninyl)] phosphate
EP3572410B1 (en) * 2014-08-25 2022-07-20 Medivir Aktiebolag Dioxolane analogues of uridine for the treatment of cancer
GB201417644D0 (en) 2014-10-06 2014-11-19 Nucana Biomed Ltd Method of separating phosphate diastereoisomers
CN105646629A (zh) 2014-11-25 2016-06-08 广州市恒诺康医药科技有限公司 L-核苷类化合物及其应用
HRP20191461T1 (hr) 2014-11-28 2019-11-15 NuCana plc Novi 2' i/ili 5' derivati 3'-deoksi adenozina supstituirani aminokiselinskim esterom fosforamidata, kao antikancerogenog spoja
WO2016098123A2 (en) * 2014-12-16 2016-06-23 Laurus Labs Private Ltd A recycling process for preparing (s)-2-[(substituted-phenoxy)-phenoxy- phosphorylamino] propionic acid isopropyl ester diastereomers
WO2016145142A1 (en) 2015-03-10 2016-09-15 Emory University Nucleotide and nucleoside therapeutics compositions and uses related thereto
CN107835687A (zh) 2015-05-14 2018-03-23 努卡那有限公司 癌症治疗
CN106543252A (zh) 2015-09-16 2017-03-29 博瑞生物医药(苏州)股份有限公司 核苷氨基磷酸酯类前药的制备方法及其中间体
CN106478753A (zh) 2015-09-16 2017-03-08 博瑞生物医药(苏州)股份有限公司 一种nuc‑1031单一异构体的制备方法和用途
CN106543220A (zh) * 2015-09-16 2017-03-29 博瑞生物医药(苏州)股份有限公司 氨基磷酸酯化合物及其制备方法和晶体
PH12018500691B1 (en) 2015-10-05 2022-08-10 NuCana plc Combination therapy
EP3377512A4 (en) 2015-11-16 2019-09-18 Ichorion Therapeutics, Inc. Nucleic Acid PRODRUGS
CA3007347C (en) * 2015-12-11 2020-08-04 NuCana plc Diastereoselective synthesis of phosphate derivatives and of the gemcitabine prodrug nuc-1031
GB201522764D0 (en) 2015-12-23 2016-02-03 Nucana Biomed Ltd Formulations of phosphate derivatives
SI3393478T1 (sl) 2015-12-23 2020-07-31 NuCana plc Kombinacijska terapija
GB201609600D0 (en) 2016-06-01 2016-07-13 Nucuna Biomed Ltd Cancer treatments
GB201609602D0 (en) * 2016-06-01 2016-07-13 Nucuna Biomed Ltd Chemical compounds
GB201609601D0 (en) 2016-06-01 2016-07-13 Nucana Biomed Ltd Phosphoramidate compounds
GB201713916D0 (en) 2017-08-30 2017-10-11 Nucana Biomed Ltd Treatment regimens

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008533191A (ja) 2005-03-21 2008-08-21 ユニバーシティ、カレッジ、カーディフ、コンサルタンツ、リミテッド 癌の治療における使用のためのヌクレオシド化合物のホスホルアミデート誘導体
JP2020523378A (ja) 2017-06-14 2020-08-06 ニューカナ パブリック リミテッド カンパニー ホスフェート誘導体の合成

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2023095954A (ja) * 2017-06-14 2023-07-06 ニューカナ パブリック リミテッド カンパニー ホスフェート誘導体の合成
JP7525687B2 (ja) 2017-06-14 2024-07-30 ニューカナ パブリック リミテッド カンパニー ホスフェート誘導体の合成

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US20200181186A1 (en) 2020-06-11
SG11201911543UA (en) 2020-01-30
US11414452B2 (en) 2022-08-16
MX391332B (es) 2025-03-21
IL302559B2 (en) 2024-09-01
WO2018229495A1 (en) 2018-12-20
AU2022204691A1 (en) 2022-08-04
JP7279991B2 (ja) 2023-05-23
JP2020523381A (ja) 2020-08-06
IL312228B2 (en) 2025-06-01
US20220402962A1 (en) 2022-12-22
CN110753697A (zh) 2020-02-04
IL271159A (en) 2020-01-30
IL312228B1 (en) 2025-02-01
EP3638684C0 (en) 2026-07-08
NZ800534A (en) 2026-03-27
AU2018284131A1 (en) 2020-01-16
EP3638684B1 (en) 2026-07-08
CN110753697B (zh) 2023-10-13
JP7525687B2 (ja) 2024-07-30
ZA201908054B (en) 2026-05-27
GB201709471D0 (en) 2017-07-26
JP2026034703A (ja) 2026-02-27
MX390901B (es) 2025-03-21
CN110785425A (zh) 2020-02-11
AU2024200428C1 (en) 2026-04-30
MX2019014914A (es) 2020-02-13
JP2024138523A (ja) 2024-10-08
CN117486959A (zh) 2024-02-02
US12054511B2 (en) 2024-08-06
PH12019502825A1 (en) 2020-10-26
WO2018229493A3 (en) 2019-02-07
US20250171487A1 (en) 2025-05-29
EP3638685A1 (en) 2020-04-22
JP2023095954A (ja) 2023-07-06
MX2022003822A (es) 2022-05-25
EA201992873A1 (ru) 2020-05-19
MX2019014907A (es) 2020-02-13
KR102920287B1 (ko) 2026-01-30
AU2022204691B2 (en) 2023-11-23
SA519410795B1 (ar) 2023-11-19
KR102695300B1 (ko) 2024-08-16
KR20200016864A (ko) 2020-02-17
IL312228A (en) 2024-06-01
AU2024200428A1 (en) 2024-02-08
WO2018229493A2 (en) 2018-12-20
CA3064177A1 (en) 2018-12-20
MA49379A (fr) 2020-04-22
NZ759692A (en) 2026-03-27
EP4786476A2 (en) 2026-08-05
US20200181190A1 (en) 2020-06-11
EP3638684A2 (en) 2020-04-22
CL2019003632A1 (es) 2020-08-14
AU2024200428B2 (en) 2025-10-16
IL302559B1 (en) 2024-05-01
ES3075652T3 (en) 2026-08-06
JP2020523378A (ja) 2020-08-06
KR20240127483A (ko) 2024-08-22
IL271159B1 (en) 2023-06-01
CN110785425B (zh) 2023-11-21
BR112019026747A2 (pt) 2020-06-30
AU2018284131B2 (en) 2022-04-07
CA3065682A1 (en) 2018-12-20
US11897913B2 (en) 2024-02-13
IL302559A (en) 2023-07-01

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