FI119246B - Menetelmä (2R-3S)-(4-asetoksi-2alfa-bentsoyylioksi-5beta,20-epoksi-1,7beta,10beta-trihydroksi-9-oksotaks-11-en-13alfa-yyli)-3-tert-butoksikarbonyyliamino-3-fenyyli-2-hydroksipropionaatin trihydraatinvalmistamiseksi - Google Patents
Menetelmä (2R-3S)-(4-asetoksi-2alfa-bentsoyylioksi-5beta,20-epoksi-1,7beta,10beta-trihydroksi-9-oksotaks-11-en-13alfa-yyli)-3-tert-butoksikarbonyyliamino-3-fenyyli-2-hydroksipropionaatin trihydraatinvalmistamiseksi Download PDFInfo
- Publication number
- FI119246B FI119246B FI970069A FI970069A FI119246B FI 119246 B FI119246 B FI 119246B FI 970069 A FI970069 A FI 970069A FI 970069 A FI970069 A FI 970069A FI 119246 B FI119246 B FI 119246B
- Authority
- FI
- Finland
- Prior art keywords
- acetoxy
- epoxy
- benzoyloxy
- trihydroxy
- phenyl
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- 238000000034 method Methods 0.000 title claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 9
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
- 238000002425 crystallisation Methods 0.000 claims description 6
- 230000008025 crystallization Effects 0.000 claims description 6
- 150000004684 trihydrates Chemical class 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- ZVAFCKLQJCZGAP-WDEREUQCSA-N (2r,3s)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H]([C@@H](O)C(O)=O)C1=CC=CC=C1 ZVAFCKLQJCZGAP-WDEREUQCSA-N 0.000 abstract 1
- PSSVSAXRAMDXPH-DELBANIYSA-N O.O.O.C(C)(C)(C)OC(=O)N[C@H]([C@H](C(=O)O)O)C1=CC=CC=C1 Chemical compound O.O.O.C(C)(C)(C)OC(=O)N[C@H]([C@H](C(=O)O)O)C1=CC=CC=C1 PSSVSAXRAMDXPH-DELBANIYSA-N 0.000 abstract 1
- 239000013078 crystal Substances 0.000 description 5
- 239000006188 syrup Substances 0.000 description 5
- 235000020357 syrup Nutrition 0.000 description 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000008213 purified water Substances 0.000 description 3
- 229960005070 ascorbic acid Drugs 0.000 description 2
- 235000010323 ascorbic acid Nutrition 0.000 description 2
- 239000011668 ascorbic acid Substances 0.000 description 2
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 2
- VJKGUHZEQQUQNR-UHFFFAOYSA-N phenyl 2-hydroxypropanoate Chemical compound CC(O)C(=O)OC1=CC=CC=C1 VJKGUHZEQQUQNR-UHFFFAOYSA-N 0.000 description 2
- GOTMYRUZLYVSPC-UHFFFAOYSA-N 2-hydroxy-2-isocyanato-3-phenylpropanoic acid Chemical compound C(=O)=NC(C(=O)O)(CC1=CC=CC=C1)O GOTMYRUZLYVSPC-UHFFFAOYSA-N 0.000 description 1
- SZLGBSFWUHJZCR-UHFFFAOYSA-N CCCCOC(=O)OC(=O)C(CC1=CC=CC=C1)(N)O Chemical compound CCCCOC(=O)OC(=O)C(CC1=CC=CC=C1)(N)O SZLGBSFWUHJZCR-UHFFFAOYSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- XLXNTFYJBJTCLB-UHFFFAOYSA-N O.O.O.NC(C(=O)O)(CC1=CC=CC=C1)O Chemical compound O.O.O.NC(C(=O)O)(CC1=CC=CC=C1)O XLXNTFYJBJTCLB-UHFFFAOYSA-N 0.000 description 1
- XSXNTSQHYJRTEB-UHFFFAOYSA-N O.O.O.OC(C(=O)OC1=CC=CC=C1)C Chemical compound O.O.O.OC(C(=O)OC1=CC=CC=C1)C XSXNTSQHYJRTEB-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000719 anti-leukaemic effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000003780 keratinization Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/14—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Epidemiology (AREA)
- Epoxy Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9408479A FR2722191B1 (fr) | 1994-07-08 | 1994-07-08 | Procede de preparation du trihydrate du (2r,3s)-3-tertbutoxycarbonylamino-2-hydroxy-3-phenylpropionate de 4-acetoxy2alpha-benzoyloxy-5beta,20epoxy-1,7beta,10beta trihydroxy-9-oxo-tax-11-en-13alpha-yle |
| FR9408479 | 1994-07-08 | ||
| PCT/FR1995/000910 WO1996001815A1 (fr) | 1994-07-08 | 1995-07-07 | PROCEDE DE PREPARATION DU TRIHYDRATE DU (2R,3S)-3-TERT-BUTOXYCARBONYLAMINO-2-HYDROXY-3-PHENYLPROPIONATE DE 4-ACETOXY-2α-BENZOYLOXY-5β,20-EPOXY-1,7β,10β-TRIHYDROXY-9-OXO-TAX-11-EN-13α-YLE |
| FR9500910 | 1995-07-07 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI970069L FI970069L (fi) | 1997-01-07 |
| FI970069A0 FI970069A0 (fi) | 1997-01-07 |
| FI119246B true FI119246B (fi) | 2008-09-15 |
Family
ID=9465183
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI970069A FI119246B (fi) | 1994-07-08 | 1997-01-07 | Menetelmä (2R-3S)-(4-asetoksi-2alfa-bentsoyylioksi-5beta,20-epoksi-1,7beta,10beta-trihydroksi-9-oksotaks-11-en-13alfa-yyli)-3-tert-butoksikarbonyyliamino-3-fenyyli-2-hydroksipropionaatin trihydraatinvalmistamiseksi |
Country Status (38)
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| JP2001523103A (ja) | 1997-04-28 | 2001-11-20 | ローヌ−プーラン・ロレ・エス・アー | 腫瘍治療用血管形成アンタゴニストのアデノウイルスによる腫瘍内送達 |
| SE510650C2 (sv) * | 1997-05-30 | 1999-06-14 | Astra Ab | Ny förening |
| FR2794771B1 (fr) | 1999-06-11 | 2001-08-10 | Aventis Pharma Sa | Adenovirus recombinants codant pour le transporteur specifique de l'iode (nis) |
| US6266619B1 (en) * | 1999-07-20 | 2001-07-24 | Halliburton Energy Services, Inc. | System and method for real time reservoir management |
| US6853921B2 (en) | 1999-07-20 | 2005-02-08 | Halliburton Energy Services, Inc. | System and method for real time reservoir management |
| GB9920548D0 (en) * | 1999-08-31 | 1999-11-03 | Rhone Poulenc Rorer Sa | Treatment of hepatocellular carcinoma |
| US6891050B2 (en) * | 2001-08-10 | 2005-05-10 | Dabur India Limited | Process for the preparation of taxanes such as paclitaxel, docetaxel and structurally similar analogs |
| US6881852B2 (en) * | 2002-02-05 | 2005-04-19 | Dabur India Limited | Process of purification of paclitaxel and docetaxel |
| US7247738B2 (en) * | 2002-05-07 | 2007-07-24 | Dabur India Limited | Method of preparation of anticancer taxanes using 3-[(substituted-2-trialkylsilyl) ethoxycarbonyl]-5-oxazolidine carboxylic acids |
| US6900342B2 (en) * | 2002-05-10 | 2005-05-31 | Dabur India Limited | Anticancer taxanes such as paclitaxel, docetaxel and their structural analogs, and a method for the preparation thereof |
| US6838569B2 (en) * | 2002-12-16 | 2005-01-04 | Dabur India Limited | Process for preparation of paclitaxel trihydrate and docetaxel trihydrate |
| US7584165B2 (en) * | 2003-01-30 | 2009-09-01 | Landmark Graphics Corporation | Support apparatus, method and system for real time operations and maintenance |
| US8703982B2 (en) | 2003-03-17 | 2014-04-22 | Phyton Holdings Llc | Purification of taxanes |
| CN1268619C (zh) * | 2003-05-08 | 2006-08-09 | 上海迪赛诺化学制药有限公司 | 多烯紫杉醇三水化合物的制备方法 |
| FR2859996B1 (fr) * | 2003-09-19 | 2006-02-03 | Aventis Pharma Sa | Solvat acetonique du dimethoxy docetaxel et son procede de preparation |
| ATE427943T1 (de) | 2003-12-12 | 2009-04-15 | Quiral Quimica Do Brasil | Verfahren zur herstellung von wasserfreien und hydratisierten pharmazeutischen wirkstoffen (apis); aus diesen hergestellte stabile pharmazeutische zusammensetzungen und anwendungen fur diese zusammensetzungen |
| US7142986B2 (en) * | 2005-02-01 | 2006-11-28 | Smith International, Inc. | System for optimizing drilling in real time |
| CN100420681C (zh) * | 2005-04-29 | 2008-09-24 | 上海奥锐特国际贸易有限公司 | 多烯紫杉醇三水物的制备方法 |
| JP5368093B2 (ja) * | 2005-08-31 | 2013-12-18 | アブラクシス バイオサイエンス， エルエルシー | 増大した安定性を有する難水溶性薬剤の組成物および調製の方法 |
| TR200801337T1 (tr) * | 2005-08-31 | 2008-07-21 | Abraxis Bioscience, Llc. | Suda zayıf çözülebilen farmasötik ajanlar ve antimikrobiyal ajanlar içeren kompozisyonlar. |
| TW200730518A (en) * | 2005-10-12 | 2007-08-16 | Sicor Inc | Crystalline forms of docetaxel and processes for their preparation |
| KR100995390B1 (ko) | 2006-01-02 | 2010-11-19 | 주식회사 삼양제넥스 | 무정형, 무수결정형 또는 수화 결정형 도세탁셀의 제조방법 |
| MX2008009308A (es) * | 2006-01-20 | 2008-10-03 | Landmark Graphics Corp | Administracion del sistema de produccion dinamica. |
| AU2007226937A1 (en) * | 2006-03-21 | 2007-09-27 | Dr. Reddy's Laboratories Ltd. | Docetaxel polymorphs and processes |
| NZ576355A (en) * | 2006-10-20 | 2012-04-27 | Scinopharm Singapore Pte Ltd | Process for making crystalline anhydrous docetaxel |
| KR100868116B1 (ko) | 2007-04-09 | 2008-11-10 | 한미약품 주식회사 | 도세탁셀·모노프로필렌글라이콜 내포화합물 및 이의제조방법 |
| KR100878455B1 (ko) | 2007-04-10 | 2009-01-13 | 한미약품 주식회사 | 안정한 무수결정형 도세탁셀 및 이의 제조방법 |
| WO2009006590A2 (en) * | 2007-07-04 | 2009-01-08 | Dr. Reddy's Laboratories Ltd. | Docetaxel process and polymorphs |
| EP2080763A1 (en) * | 2008-01-18 | 2009-07-22 | INDENA S.p.A. | Crystalline form I of ortataxel |
| DK2080764T3 (da) * | 2008-01-18 | 2012-09-24 | Indena Spa | Faste former af ortataxel |
| PL388144A1 (pl) | 2009-05-29 | 2010-12-06 | Przedsiębiorstwo Produkcyjno-Wdrożeniowe Ifotam Spółka Z Ograniczoną Odpowiedzialnością | Solwaty (2R,3S)-3-tert-butoksykarbonylamino-2-hydroksy-3-fenylopropionianu 4-acetoksy-2α-benzoiloksy -5β,20-epoksy-1,7β,10β-trihydroksy-9-okso-taks-11-en-13α-ylu, sposób ich otrzymywania i zastosowanie |
| EP2330100B1 (en) | 2009-11-04 | 2017-01-11 | Emcure Pharmaceuticals Limited | An improved process for preparation of taxane derivatives |
| BR112012028037A2 (pt) | 2010-05-03 | 2016-08-02 | Teikoku Pharma Usa Inc | formulação de pró-emulsão líquida de taxano não aquosa, métodos para administrar um taxano a um paciente e para fabricar uma formulação de pró-emulsão de taxano, composição de emulsão de taxano, e, kit |
| WO2012160568A1 (en) * | 2011-05-23 | 2012-11-29 | Shilpa Medicare Limited | Process for preparing docetaxel trihydrate polymorph |
| ES2704632T3 (es) | 2011-09-08 | 2019-03-19 | Univ New York | Virus de herpes simplex oncolítico y sus usos terapéuticos |
| WO2013096455A1 (en) | 2011-12-20 | 2013-06-27 | Dana-Farber Cancer Institute, Inc. | Methods for diagnosing and treating oncogenic kras-associated cancer |
| LT2833905T (lt) | 2012-04-04 | 2018-07-10 | Halozyme, Inc. | Derinių terapija su hialuronidaze ir į naviką nukreiptu taksanu |
| CA2874521A1 (en) | 2012-05-24 | 2013-11-28 | Dana-Farber Cancer Institute, Inc. | Targeting the glutamine to pyruvate pathway for treatment of oncogenic kras-associated cancer |
| US20150285802A1 (en) | 2012-07-18 | 2015-10-08 | Dana-Farber Cancer Institute, Inc. | Methods for treating, preventing and predicting risk of developing breast cancer |
| JO3685B1 (ar) | 2012-10-01 | 2020-08-27 | Teikoku Pharma Usa Inc | صيغ التشتيت الجسيمي للتاكسين غير المائي وطرق استخدامها |
| EP2968406A4 (en) | 2013-03-14 | 2016-10-26 | Icahn School Med Mount Sinai | WITH AUTOLOGOUS TUMORLYSAT-LOADED DENDRITIC CELL VACCINE FOR THE TREATMENT OF LIVER CANCER |
| US10130590B2 (en) | 2013-10-01 | 2018-11-20 | Dana-Farber Cancer Institute, Inc. | Methods of treating cancer with atovaquone-related compounds |
| WO2015149006A2 (en) | 2014-03-27 | 2015-10-01 | Dana-Farber Cancer Institute, Inc. | Compositions and methods for modulating ncoa4-mediated autophagic targeting of ferritin |
| MA39818A (fr) | 2014-03-30 | 2017-02-08 | Benevir Biopharm Inc | Virus oncolytiques « armés » comprenant un inhibiteur de tap exogène et leurs utilisations thérapeutiques |
| EP3307330B1 (en) | 2015-06-15 | 2021-03-10 | New York University | Method of treatment using oncolytic viruses |
| WO2019222435A1 (en) | 2018-05-16 | 2019-11-21 | Halozyme, Inc. | Methods of selecting subjects for combination cancer therapy with a polymer-conjugated soluble ph20 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2601675B1 (fr) * | 1986-07-17 | 1988-09-23 | Rhone Poulenc Sante | Derives du taxol, leur preparation et les compositions pharmaceutiques qui les contiennent |
| US5229526A (en) * | 1991-09-23 | 1993-07-20 | Florida State University | Metal alkoxides |
-
1994
- 1994-07-08 FR FR9408479A patent/FR2722191B1/fr not_active Expired - Fee Related
-
1995
- 1995-06-22 IL IL11427495A patent/IL114274A/xx not_active IP Right Cessation
- 1995-07-03 UY UY23991A patent/UY23991A1/es not_active IP Right Cessation
- 1995-07-04 DZ DZ950082A patent/DZ1905A1/fr active
- 1995-07-05 TN TNTNSN95071A patent/TNSN95071A1/fr unknown
- 1995-07-05 PE PE1995272899A patent/PE8697A1/es not_active IP Right Cessation
- 1995-07-06 MA MA23945A patent/MA23606A1/fr unknown
- 1995-07-06 IN IN1260DE1995 patent/IN183947B/en unknown
- 1995-07-06 MY MYPI95001895A patent/MY118481A/en unknown
- 1995-07-06 TW TW084106974A patent/TW419473B/zh not_active IP Right Cessation
- 1995-07-06 ZA ZA955646A patent/ZA955646B/xx unknown
- 1995-07-07 KR KR1019970700118A patent/KR100391753B1/ko not_active Expired - Lifetime
- 1995-07-07 AT AT95925022T patent/ATE171702T1/de active
- 1995-07-07 PL PL95318195A patent/PL179876B1/pl unknown
- 1995-07-07 SI SI9530138T patent/SI0770070T1/xx unknown
- 1995-07-07 DK DK95925022T patent/DK0770070T3/da active
- 1995-07-07 WO PCT/FR1995/000910 patent/WO1996001815A1/fr not_active Ceased
- 1995-07-07 AU AU29305/95A patent/AU706519B2/en not_active Expired
- 1995-07-07 CA CA002193531A patent/CA2193531C/fr not_active Expired - Lifetime
- 1995-07-07 US US08/776,333 patent/US6022985A/en not_active Expired - Lifetime
- 1995-07-07 DE DE69505128T patent/DE69505128T2/de not_active Expired - Lifetime
- 1995-07-07 EP EP95925022A patent/EP0770070B1/fr not_active Expired - Lifetime
- 1995-07-07 CZ CZ9735A patent/CZ284695B6/cs not_active IP Right Cessation
- 1995-07-07 RU RU97101875A patent/RU2126397C1/ru active
- 1995-07-07 SK SK6-97A patent/SK280520B6/sk not_active IP Right Cessation
- 1995-07-07 CN CN95193984A patent/CN1067996C/zh not_active Expired - Lifetime
- 1995-07-07 ES ES95925022T patent/ES2121404T3/es not_active Expired - Lifetime
- 1995-07-07 JP JP50415896A patent/JP3753155B2/ja not_active Expired - Fee Related
- 1995-07-07 NZ NZ289455A patent/NZ289455A/en not_active IP Right Cessation
- 1995-07-07 CO CO95029779A patent/CO4410189A1/es unknown
- 1995-07-07 MX MX9700173A patent/MX9700173A/es unknown
- 1995-07-07 BR BR9508789A patent/BR9508789A/pt not_active Application Discontinuation
- 1995-07-07 HU HU9700041A patent/HU220634B1/hu unknown
- 1995-07-07 UA UA97010077A patent/UA51624C2/uk unknown
-
1997
- 1997-01-02 NO NO19970007A patent/NO314500B1/no not_active IP Right Cessation
- 1997-01-07 IS IS4411A patent/IS2032B/is unknown
- 1997-01-07 FI FI970069A patent/FI119246B/fi not_active IP Right Cessation
-
1998
- 1998-01-01 GR GR980400355T patent/GR3027558T3/el unknown
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