JP2005537255A5 - - Google Patents
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- Publication number
- JP2005537255A5 JP2005537255A5 JP2004519472A JP2004519472A JP2005537255A5 JP 2005537255 A5 JP2005537255 A5 JP 2005537255A5 JP 2004519472 A JP2004519472 A JP 2004519472A JP 2004519472 A JP2004519472 A JP 2004519472A JP 2005537255 A5 JP2005537255 A5 JP 2005537255A5
- Authority
- JP
- Japan
- Prior art keywords
- oxy
- benzofuran
- spiro
- hydroxypropyl
- chloro
- 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.)
- Pending
Links
- -1 cyano, hydroxyl Chemical group 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000000668 atmospheric pressure chemical ionisation mass spectrometry Methods 0.000 description 9
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- KZKMLWNOMSOSNT-LMOVPXPDSA-N 2-[(2s)-3-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-2-hydroxypropoxy]-4-hydroxybenzoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C([C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1)OC1=CC(O)=CC=C1C(O)=O KZKMLWNOMSOSNT-LMOVPXPDSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- JXHYCCGOZUGBFD-UHFFFAOYSA-N benzoic acid;hydrochloride Chemical compound Cl.OC(=O)C1=CC=CC=C1 JXHYCCGOZUGBFD-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
- XCUAIINAJCDIPM-XVFCMESISA-N N(4)-hydroxycytidine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=NO)C=C1 XCUAIINAJCDIPM-XVFCMESISA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- XTKDAFGWCDAMPY-UHFFFAOYSA-N azaperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2N=CC=CC=2)CC1 XTKDAFGWCDAMPY-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- FRCSGPIZMKPBKK-NRFANRHFSA-N n-(2-acetamidoethyl)-2-[(2s)-3-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-2-hydroxypropoxy]-4-hydroxybenzamide Chemical compound CC(=O)NCCNC(=O)C1=CC=C(O)C=C1OC[C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1 FRCSGPIZMKPBKK-NRFANRHFSA-N 0.000 description 1
- DAKZISABEDGGSV-UHFFFAOYSA-N n-(2-aminoethyl)acetamide Chemical compound CC(=O)NCCN DAKZISABEDGGSV-UHFFFAOYSA-N 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 description 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0202133A SE0202133D0 (sv) | 2002-07-08 | 2002-07-08 | Novel compounds |
| PCT/SE2003/001185 WO2004005295A1 (en) | 2002-07-08 | 2003-07-07 | Novel tricyclic spiropiperidines or spiropyrrolidines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005537255A JP2005537255A (ja) | 2005-12-08 |
| JP2005537255A5 true JP2005537255A5 (https=) | 2006-08-31 |
Family
ID=20288470
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004519472A Pending JP2005537255A (ja) | 2002-07-08 | 2003-07-07 | 新規三環式スピロピペリジンまたはスピロピロリジン |
Country Status (25)
| Country | Link |
|---|---|
| US (2) | US7449475B2 (https=) |
| EP (1) | EP1521757B1 (https=) |
| JP (1) | JP2005537255A (https=) |
| CN (2) | CN1974574A (https=) |
| AR (1) | AR040475A1 (https=) |
| AT (1) | ATE385235T1 (https=) |
| AU (1) | AU2003243122B2 (https=) |
| BR (1) | BR0312560A (https=) |
| CA (1) | CA2492122A1 (https=) |
| CY (1) | CY1107915T1 (https=) |
| DE (1) | DE60318948T2 (https=) |
| DK (1) | DK1521757T3 (https=) |
| ES (1) | ES2298575T3 (https=) |
| IS (1) | IS7662A (https=) |
| MX (1) | MXPA05000278A (https=) |
| NO (1) | NO20050635L (https=) |
| NZ (1) | NZ537259A (https=) |
| PL (1) | PL374877A1 (https=) |
| PT (1) | PT1521757E (https=) |
| RU (1) | RU2320664C2 (https=) |
| SE (1) | SE0202133D0 (https=) |
| TW (1) | TW200413386A (https=) |
| UA (1) | UA77809C2 (https=) |
| WO (1) | WO2004005295A1 (https=) |
| ZA (1) | ZA200500024B (https=) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE0202133D0 (sv) | 2002-07-08 | 2002-07-08 | Astrazeneca Ab | Novel compounds |
| EP1661889A4 (en) * | 2003-09-05 | 2009-08-05 | Ono Pharmaceutical Co | ANTAGONIST OF THE CHEMOKINE RECEPTOR AND ITS USE FOR MEDICAL PURPOSES |
| US20070021498A1 (en) * | 2004-10-14 | 2007-01-25 | Nafizal Hossain | Novel tricyclic spiroderivatives as modulators of chemokine receptor activity |
| SE0302755D0 (sv) * | 2003-10-17 | 2003-10-17 | Astrazeneca Ab | Novel compounds |
| SE0302811D0 (sv) * | 2003-10-23 | 2003-10-23 | Astrazeneca Ab | Novel compounds |
| SE0303090D0 (sv) * | 2003-11-20 | 2003-11-20 | Astrazeneca Ab | Novel compounds |
| SE0303280D0 (sv) * | 2003-12-05 | 2003-12-05 | Astrazeneca Ab | Novel compounds |
| SE0303541D0 (sv) | 2003-12-22 | 2003-12-22 | Astrazeneca Ab | New compounds |
| TWI350168B (en) | 2004-05-07 | 2011-10-11 | Incyte Corp | Amido compounds and their use as pharmaceuticals |
| US8071624B2 (en) | 2004-06-24 | 2011-12-06 | Incyte Corporation | N-substituted piperidines and their use as pharmaceuticals |
| KR101411167B1 (ko) | 2005-04-13 | 2014-06-23 | 아스텍스 테라퓨틱스 리미티드 | 하이드록시벤즈아미드 유도체 및 ｈｓｐ90 억제제로서의이의 용도 |
| WO2007028638A1 (en) | 2005-09-09 | 2007-03-15 | Euro-Celtique S.A. | Fused and spirocycle compounds and the use thereof |
| JP5315590B2 (ja) * | 2006-02-14 | 2013-10-16 | Ｊｎｃ株式会社 | 液晶化合物、液晶組成物および液晶表示素子 |
| US7754725B2 (en) | 2006-03-01 | 2010-07-13 | Astex Therapeutics Ltd. | Dihydroxyphenyl isoindolymethanones |
| BRPI0714463A2 (pt) * | 2006-07-19 | 2013-04-02 | Astrazeneca Ab | compostos de espiropiperidina tricÍclicos, sua sÍntese e seus usos como moduladores de atividade receptora de quimiocina |
| JP5410285B2 (ja) | 2006-10-12 | 2014-02-05 | アステックス、セラピューティックス、リミテッド | 医薬化合物 |
| WO2008044041A1 (en) | 2006-10-12 | 2008-04-17 | Astex Therapeutics Limited | Pharmaceutical combinations |
| JP5528807B2 (ja) | 2006-10-12 | 2014-06-25 | アステックス、セラピューティックス、リミテッド | 複合薬剤 |
| JP5518478B2 (ja) | 2006-10-12 | 2014-06-11 | アステックス、セラピューティックス、リミテッド | 医薬化合物 |
| EP2073802A1 (en) | 2006-10-12 | 2009-07-01 | Astex Therapeutics Limited | Pharmaceutical combinations |
| GB0620259D0 (en) | 2006-10-12 | 2006-11-22 | Astex Therapeutics Ltd | Pharmaceutical compounds |
| CA2674237C (en) | 2006-12-28 | 2015-11-24 | Rigel Pharmaceuticals, Inc. | N-substituted-heterocycloalkyloxybenzamide compounds and methods of use |
| US20110136843A1 (en) * | 2007-02-23 | 2011-06-09 | Tomas Eriksson | Novel Combination of Compounds to be Used in the Treatment of Airway Diseases, Especially Chronic Obstructive Pulmonary Disease (COPD) and Asthma |
| WO2008103126A1 (en) * | 2007-02-23 | 2008-08-28 | Astrazeneca Ab | Novel combination of compounds to be used in the treatment of airway diseases, especially chronic obstructive pulmonary disease (copd) and asthma |
| WO2008121066A1 (en) * | 2007-03-30 | 2008-10-09 | Astrazeneca Ab | Novel tricyclic spiropiperidines or spiropyrrolidines and their use as modulators of chemokine receptors |
| TW200904423A (en) * | 2007-06-20 | 2009-02-01 | Glaxo Group Ltd | Spiroindolines as modulators of chemokine receptors |
| WO2009011654A1 (en) * | 2007-07-17 | 2009-01-22 | Astrazeneca Ab | Process for the preparation of cyclic spiropiperidines |
| WO2009011655A1 (en) * | 2007-07-17 | 2009-01-22 | Astrazeneca Ab | Splropiperidine compounds, a process of their preparation, pharmaceutical compositions containing them, and their use in the treatment of airway diseases, inflammatory diseases, copd or asthma |
| US8536198B2 (en) * | 2007-07-24 | 2013-09-17 | Bristol-Myers Squibb Company | Piperidine derivatives as modulators of chemokine receptor activity |
| JP2010536779A (ja) * | 2007-08-14 | 2010-12-02 | グラクソ グループ リミテッド | ケモカイン受容体のモジュレーターとしてのスピロインデンおよびスピロインダン |
| WO2009061881A1 (en) * | 2007-11-07 | 2009-05-14 | Glaxo Group Limited | Spirodihydrobenzofurans as modulators of chemokine receptors |
| MX2010008375A (es) * | 2008-01-30 | 2011-03-04 | Cephalon Inc Star | Derivados de piperidina espirocíclicos substituidos como ligandos de receptores de histamina-3 (h3). |
| FR2928150A1 (fr) | 2008-02-29 | 2009-09-04 | Vetoquinol Sa Sa | Nouveaux derives 7-substitues de 3-carboxy-oxadiazino-quinolones, leur preparation et leur application comme anti-bacteriens |
| GB0806527D0 (en) | 2008-04-11 | 2008-05-14 | Astex Therapeutics Ltd | Pharmaceutical compounds |
| EP2145891A1 (en) | 2008-07-09 | 2010-01-20 | Vetoquinol S.A. | 9-substituted-5-carboxy-oxadiazino-quinolone derivatives, their preparation and their application as anti-bacterials |
| AR078948A1 (es) * | 2009-11-30 | 2011-12-14 | Lilly Co Eli | Compuestos de espiropiperidina, composicion farmaceutica que lo comprenden y su uso para preparar un medicamento util para tratar la diabetes |
| US10752588B2 (en) | 2014-12-19 | 2020-08-25 | The Broad Institute, Inc. | Dopamine D2 receptor ligands |
| WO2016100940A1 (en) | 2014-12-19 | 2016-06-23 | The Broad Institute, Inc. | Dopamine d2 receptor ligands |
| EP3668840A1 (en) | 2017-08-15 | 2020-06-24 | Inflazome Limited | Novel sulfonamide carboxamide compounds |
| CN115397811B (zh) | 2020-01-20 | 2025-05-23 | 奈奥芬莱有限公司 | 与atp结合位点结合的异吲哚啉衍生物 |
| GB202008201D0 (en) * | 2020-06-01 | 2020-07-15 | Neophore Ltd | Inhibitor compounds |
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| SE0302811D0 (sv) | 2003-10-23 | 2003-10-23 | Astrazeneca Ab | Novel compounds |
| SE0303090D0 (sv) | 2003-11-20 | 2003-11-20 | Astrazeneca Ab | Novel compounds |
| SE0303280D0 (sv) | 2003-12-05 | 2003-12-05 | Astrazeneca Ab | Novel compounds |
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-
2002
- 2002-07-08 SE SE0202133A patent/SE0202133D0/xx unknown
-
2003
- 2003-07-03 TW TW092118200A patent/TW200413386A/zh unknown
- 2003-07-07 CN CNA2006101435561A patent/CN1974574A/zh active Pending
- 2003-07-07 BR BR0312560-2A patent/BR0312560A/pt not_active IP Right Cessation
- 2003-07-07 CA CA002492122A patent/CA2492122A1/en not_active Abandoned
- 2003-07-07 WO PCT/SE2003/001185 patent/WO2004005295A1/en not_active Ceased
- 2003-07-07 JP JP2004519472A patent/JP2005537255A/ja active Pending
- 2003-07-07 RU RU2004137278/04A patent/RU2320664C2/ru not_active IP Right Cessation
- 2003-07-07 PL PL03374877A patent/PL374877A1/xx not_active Application Discontinuation
- 2003-07-07 AU AU2003243122A patent/AU2003243122B2/en not_active Ceased
- 2003-07-07 PT PT03762957T patent/PT1521757E/pt unknown
- 2003-07-07 EP EP03762957A patent/EP1521757B1/en not_active Expired - Lifetime
- 2003-07-07 NZ NZ537259A patent/NZ537259A/en unknown
- 2003-07-07 DK DK03762957T patent/DK1521757T3/da active
- 2003-07-07 DE DE60318948T patent/DE60318948T2/de not_active Expired - Fee Related
- 2003-07-07 MX MXPA05000278A patent/MXPA05000278A/es active IP Right Grant
- 2003-07-07 ES ES03762957T patent/ES2298575T3/es not_active Expired - Lifetime
- 2003-07-07 US US10/520,699 patent/US7449475B2/en not_active Expired - Fee Related
- 2003-07-07 UA UA20041210166A patent/UA77809C2/uk unknown
- 2003-07-07 CN CNB038191466A patent/CN1326858C/zh not_active Expired - Fee Related
- 2003-07-07 AT AT03762957T patent/ATE385235T1/de not_active IP Right Cessation
- 2003-07-08 AR AR20030102463A patent/AR040475A1/es not_active Application Discontinuation
-
2005
- 2005-01-03 ZA ZA200500024A patent/ZA200500024B/xx unknown
- 2005-01-24 IS IS7662A patent/IS7662A/is unknown
- 2005-02-04 NO NO20050635A patent/NO20050635L/no not_active Application Discontinuation
-
2008
- 2008-04-03 CY CY20081100375T patent/CY1107915T1/el unknown
- 2008-11-05 US US12/265,251 patent/US20090062322A1/en not_active Abandoned
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