JP2002533470A5 - - Google Patents
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- Publication number
- JP2002533470A5 JP2002533470A5 JP2000591054A JP2000591054A JP2002533470A5 JP 2002533470 A5 JP2002533470 A5 JP 2002533470A5 JP 2000591054 A JP2000591054 A JP 2000591054A JP 2000591054 A JP2000591054 A JP 2000591054A JP 2002533470 A5 JP2002533470 A5 JP 2002533470A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- nucleoside
- hydroxymethyl
- amino
- alkyl
- 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
- 150000001875 compounds Chemical class 0.000 description 25
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 8
- 239000002777 nucleoside Substances 0.000 description 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 7
- 150000003833 nucleoside derivatives Chemical class 0.000 description 7
- 208000036142 Viral infection Diseases 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 230000009385 viral infection Effects 0.000 description 5
- -1 Carbonyl Chemical group 0.000 description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- 208000031886 HIV Infections Diseases 0.000 description 2
- 208000037357 HIV infectious disease Diseases 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- WHBIGIKBNXZKFE-UHFFFAOYSA-N delavirdine Chemical compound CC(C)NC1=CC=CN=C1N1CCN(C(=O)C=2NC3=CC=C(NS(C)(=O)=O)C=C3C=2)CC1 WHBIGIKBNXZKFE-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical group C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 description 2
- 229940042402 non-nucleoside reverse transcriptase inhibitor Drugs 0.000 description 2
- 239000002726 nonnucleoside reverse transcriptase inhibitor Substances 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 0 CN(C1*(*)CC1)c1nc(N)nc2c1nc[n]2C1OC(CO*)OC1 Chemical compound CN(C1*(*)CC1)c1nc(N)nc2c1nc[n]2C1OC(CO*)OC1 0.000 description 1
- QAGYKUNXZHXKMR-UHFFFAOYSA-N CPD000469186 Natural products CC1=C(O)C=CC=C1C(=O)NC(C(O)CN1C(CC2CCCCC2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-UHFFFAOYSA-N 0.000 description 1
- BXZVVICBKDXVGW-NKWVEPMBSA-N Didanosine Chemical compound O1[C@H](CO)CC[C@@H]1N1C(NC=NC2=O)=C2N=C1 BXZVVICBKDXVGW-NKWVEPMBSA-N 0.000 description 1
- XPOQHMRABVBWPR-UHFFFAOYSA-N Efavirenz Natural products O1C(=O)NC2=CC=C(Cl)C=C2C1(C(F)(F)F)C#CC1CC1 XPOQHMRABVBWPR-UHFFFAOYSA-N 0.000 description 1
- 229940122313 Nucleoside reverse transcriptase inhibitor Drugs 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 229940124158 Protease/peptidase inhibitor Drugs 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- NCDNCNXCDXHOMX-UHFFFAOYSA-N Ritonavir Natural products C=1C=CC=CC=1CC(NC(=O)OCC=1SC=NC=1)C(O)CC(CC=1C=CC=CC=1)NC(=O)C(C(C)C)NC(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-UHFFFAOYSA-N 0.000 description 1
- XNKLLVCARDGLGL-JGVFFNPUSA-N Stavudine Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1C=C[C@@H](CO)O1 XNKLLVCARDGLGL-JGVFFNPUSA-N 0.000 description 1
- WREGKURFCTUGRC-POYBYMJQSA-N Zalcitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)CC1 WREGKURFCTUGRC-POYBYMJQSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229960005319 delavirdine Drugs 0.000 description 1
- 229960002656 didanosine Drugs 0.000 description 1
- 239000001177 diphosphate Substances 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000002651 drug therapy Methods 0.000 description 1
- 229960003804 efavirenz Drugs 0.000 description 1
- XPOQHMRABVBWPR-ZDUSSCGKSA-N efavirenz Chemical compound C([C@]1(C2=CC(Cl)=CC=C2NC(=O)O1)C(F)(F)F)#CC1CC1 XPOQHMRABVBWPR-ZDUSSCGKSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229960001936 indinavir Drugs 0.000 description 1
- CBVCZFGXHXORBI-PXQQMZJSSA-N indinavir Chemical group C([C@H](N(CC1)C[C@@H](O)C[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H]2C3=CC=CC=C3C[C@H]2O)C(=O)NC(C)(C)C)N1CC1=CC=CN=C1 CBVCZFGXHXORBI-PXQQMZJSSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229960001627 lamivudine Drugs 0.000 description 1
- JTEGQNOMFQHVDC-NKWVEPMBSA-N lamivudine Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)SC1 JTEGQNOMFQHVDC-NKWVEPMBSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000004712 monophosphates Chemical class 0.000 description 1
- 229960000884 nelfinavir Drugs 0.000 description 1
- QAGYKUNXZHXKMR-HKWSIXNMSA-N nelfinavir Chemical compound CC1=C(O)C=CC=C1C(=O)N[C@H]([C@H](O)CN1[C@@H](C[C@@H]2CCCC[C@@H]2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-HKWSIXNMSA-N 0.000 description 1
- 229960000689 nevirapine Drugs 0.000 description 1
- 229940127073 nucleoside analogue Drugs 0.000 description 1
- 125000003835 nucleoside group Chemical group 0.000 description 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229960000311 ritonavir Drugs 0.000 description 1
- NCDNCNXCDXHOMX-XGKFQTDJSA-N ritonavir Chemical compound N([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1SC=NC=1)CC=1C=CC=CC=1)C(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-XGKFQTDJSA-N 0.000 description 1
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 description 1
- 229960001852 saquinavir Drugs 0.000 description 1
- QWAXKHKRTORLEM-UGJKXSETSA-N saquinavir Chemical compound C([C@@H]([C@H](O)CN1C[C@H]2CCCC[C@H]2C[C@H]1C(=O)NC(C)(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)C=1N=C2C=CC=CC2=CC=1)C1=CC=CC=C1 QWAXKHKRTORLEM-UGJKXSETSA-N 0.000 description 1
- 229960001203 stavudine Drugs 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- 235000011178 triphosphate Nutrition 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 229960000523 zalcitabine Drugs 0.000 description 1
- 229960002555 zidovudine Drugs 0.000 description 1
- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11379798P | 1998-12-23 | 1998-12-23 | |
| US60/113,797 | 1998-12-23 | ||
| PCT/CA1999/001229 WO2000039143A2 (en) | 1998-12-23 | 1999-12-22 | Antiviral nucleoside analogues |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002533470A JP2002533470A (ja) | 2002-10-08 |
| JP2002533470A5 true JP2002533470A5 (enExample) | 2007-02-15 |
Family
ID=22351590
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000591054A Pending JP2002533470A (ja) | 1998-12-23 | 1999-12-22 | 抗ウイルス性ヌクレオシド類似体 |
Country Status (27)
| Country | Link |
|---|---|
| US (3) | US6358963B1 (enExample) |
| EP (1) | EP1140937B1 (enExample) |
| JP (1) | JP2002533470A (enExample) |
| KR (1) | KR100653485B1 (enExample) |
| CN (1) | CN1117751C (enExample) |
| AP (1) | AP2001002207A0 (enExample) |
| AT (1) | ATE254126T1 (enExample) |
| AU (1) | AU760875B2 (enExample) |
| BR (1) | BR9916849A (enExample) |
| CA (1) | CA2355712C (enExample) |
| CZ (1) | CZ20012352A3 (enExample) |
| DE (1) | DE69912842T2 (enExample) |
| DK (1) | DK1140937T3 (enExample) |
| EA (1) | EA004767B1 (enExample) |
| ES (1) | ES2209532T3 (enExample) |
| HU (1) | HUP0104827A3 (enExample) |
| ID (1) | ID30477A (enExample) |
| IL (1) | IL143867A0 (enExample) |
| MX (1) | MXPA01006425A (enExample) |
| NO (1) | NO20013163L (enExample) |
| NZ (1) | NZ513094A (enExample) |
| OA (1) | OA11741A (enExample) |
| PT (1) | PT1140937E (enExample) |
| TR (1) | TR200102501T2 (enExample) |
| UY (1) | UY25878A1 (enExample) |
| WO (1) | WO2000039143A2 (enExample) |
| ZA (1) | ZA200105702B (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA004767B1 (ru) * | 1998-12-23 | 2004-08-26 | Шайре Байокем Инк. | Аналоги нуклеозида (варианты) и их применение, комбинация и способ лечения вирусных инфекций, фармацевтическая композиция |
| AU3144801A (en) * | 2000-02-11 | 2001-08-20 | Shire Biochem Inc. | Stereoselective synthesis of nucleoside analogues |
| WO2004009595A1 (en) * | 2002-07-03 | 2004-01-29 | Triangle Pharmaceuticals, Inc. | Combination therapy with 1,3-dioxolanes and inosine monophosphate dehydrogenase inhibitors |
| IL166682A0 (en) | 2002-08-06 | 2006-01-15 | Pharmasset Ltd | Processes for preparing 1,3-dioxolane nucleosides |
| US7706405B2 (en) * | 2002-09-12 | 2010-04-27 | Interdigital Technology Corporation | System for efficient recovery of Node-B buffered data following MAC layer reset |
| WO2004048590A1 (en) * | 2002-11-18 | 2004-06-10 | Shire Biochem Inc. | Stereoselective process for the production of dioxolane nucleoside analogues |
| DE10335061B4 (de) * | 2003-07-31 | 2005-11-17 | Wacker-Chemie Gmbh | Verfahren zur Herstellung von OH-geschützten [4-(2,6-damino-9H-purin-9-yl)-1,3-dioxolan-2-yl]methanol-Derivaten |
| KR101157468B1 (ko) * | 2004-02-03 | 2012-07-06 | 에모리 유니버시티 | 1,3-디옥솔란 뉴클레오시드 제조방법 |
| US7322412B2 (en) * | 2004-08-30 | 2008-01-29 | Halliburton Energy Services, Inc. | Casing shoes and methods of reverse-circulation cementing of casing |
| EP2105412B1 (de) * | 2008-03-20 | 2011-07-13 | Befesa Salzschlacke Gmbh | Hochtonerdehaltiger Rohstoff und Verfahren zur Herstellung |
| WO2012048455A1 (zh) * | 2010-10-12 | 2012-04-19 | 武汉大学 | 一种抗病毒透皮吸收贴片及其制备方法 |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4000137A (en) | 1975-06-10 | 1976-12-28 | American Home Products Corporation | Antitumor derivatives of periodate-oxidized nucleosides |
| US4041037A (en) | 1975-06-10 | 1977-08-09 | American Home Products Corporation | Antitumor derivatives of periodate-oxidized cytidine |
| JPS5668674A (en) | 1979-11-08 | 1981-06-09 | Shionogi & Co Ltd | 5-fluorouracil derivative |
| JPS5738774A (en) | 1980-08-19 | 1982-03-03 | Chugai Pharmaceut Co Ltd | Uracil derivative and its preparation |
| US4479942A (en) | 1981-08-10 | 1984-10-30 | Fujisawa Pharmaceutical Co., Ltd. | Tetrahydrofurnancarboxylic acid derivatives, processes for preparation thereof and pharmaceutical compositions thereof |
| IL86007A0 (en) * | 1987-04-09 | 1988-09-30 | Wellcome Found | 6-substituted purine nucleosides,their preparation and pharmaceutical compositions containing them |
| HU198933B (en) | 1987-11-02 | 1989-12-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing new xanthine derivatives and pharmaceutical compositions comprising same as active ingredient |
| NZ228645A (en) | 1988-04-11 | 1991-09-25 | Iaf Biochem Int | 1,3-dioxolane derivatives substituted in the 5th position by a purine or pyrimidine radical; treatment of viral infections |
| US5041449A (en) | 1988-04-11 | 1991-08-20 | Iaf Biochem International, Inc. | 4-(nucleoside base)-substituted-1,3-dioxolanes useful for treatment of retroviral infections |
| US5047407A (en) | 1989-02-08 | 1991-09-10 | Iaf Biochem International, Inc. | 2-substituted-5-substituted-1,3-oxathiolanes with antiviral properties |
| US5270315A (en) | 1988-04-11 | 1993-12-14 | Biochem Pharma Inc. | 4-(purinyl bases)-substituted-1,3-dioxlanes |
| US4987224A (en) | 1988-08-02 | 1991-01-22 | University Of Georgia Research Foundation, Inc. | Method of preparation of 2',3'-dideoxynucleosides |
| WO1994014802A1 (en) | 1989-02-08 | 1994-07-07 | Biochem Pharma Inc. | Process for preparing substituted 1,3-oxathiolanes with antiviral properties |
| PT95516A (pt) * | 1989-10-06 | 1991-08-14 | Wellcome Found | Processo para a preparacao de derivados de 2',3'-didesoxi nucleosidos 6-substituidos |
| US5276151A (en) | 1990-02-01 | 1994-01-04 | Emory University | Method of synthesis of 1,3-dioxolane nucleosides |
| US5204466A (en) | 1990-02-01 | 1993-04-20 | Emory University | Method and compositions for the synthesis of bch-189 and related compounds |
| US5700937A (en) | 1990-02-01 | 1997-12-23 | Emory University | Method for the synthesis, compositions and use of 2'-deoxy-5-fluoro-3'-thiacytidine and related compounds |
| US6642245B1 (en) | 1990-02-01 | 2003-11-04 | Emory University | Antiviral activity and resolution of 2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane |
| GB9009861D0 (en) | 1990-05-02 | 1990-06-27 | Glaxo Group Ltd | Chemical compounds |
| CA2095613C (en) | 1990-11-13 | 2001-01-02 | Bernard Belleau | Substituted 1, 3-oxathiolanes and substituted 1, 3-dithiolanes with antiviral properties |
| WO1992010496A1 (en) | 1990-12-05 | 1992-06-25 | University Of Georgia Research Foundation, Inc. | ENANTIOMERICALLY PURE β-L-(-)-1,3-OXATHIOLANE NUCLEOSIDES |
| US5179104A (en) | 1990-12-05 | 1993-01-12 | University Of Georgia Research Foundation, Inc. | Process for the preparation of enantiomerically pure β-D-(-)-dioxolane-nucleosides |
| US5925643A (en) * | 1990-12-05 | 1999-07-20 | Emory University | Enantiomerically pure β-D-dioxolane-nucleosides |
| US5444063A (en) | 1990-12-05 | 1995-08-22 | Emory University | Enantiomerically pure β-D-dioxolane nucleosides with selective anti-Hepatitis B virus activity |
| NZ241625A (en) | 1991-02-22 | 1996-03-26 | Univ Emory | 1,3-oxathiolane derivatives, anti-viral compositions containing such and method of resolving racemic mixture of enantiomers |
| WO1992018517A1 (en) | 1991-04-17 | 1992-10-29 | Yale University | Method of treating or preventing hepatitis b virus |
| GB9109506D0 (en) | 1991-05-02 | 1991-06-26 | Wellcome Found | Therapeutic nucleosides |
| GB9110874D0 (en) | 1991-05-20 | 1991-07-10 | Iaf Biochem Int | Medicaments |
| ZA923640B (en) | 1991-05-21 | 1993-02-24 | Iaf Biochem Int | Processes for the diastereoselective synthesis of nucleosides |
| GB9200150D0 (en) | 1992-01-06 | 1992-02-26 | Wellcome Found | Therapeutic nucleosides |
| US5869461A (en) | 1995-03-16 | 1999-02-09 | Yale University | Reducing toxicity of L-nucleosides with D-nucleosides |
| GB9525606D0 (en) * | 1995-12-14 | 1996-02-14 | Iaf Biochem Int | Method and compositions for the synthesis of dioxolane nucleosides with - configuration |
| US5792773A (en) | 1996-11-15 | 1998-08-11 | Yale University | L-β-dioxolane uridine analog administration for treating Epstein-Barr virus infection |
| EA004767B1 (ru) * | 1998-12-23 | 2004-08-26 | Шайре Байокем Инк. | Аналоги нуклеозида (варианты) и их применение, комбинация и способ лечения вирусных инфекций, фармацевтическая композиция |
-
1999
- 1999-12-22 EA EA200100711A patent/EA004767B1/ru not_active IP Right Cessation
- 1999-12-22 PT PT99960757T patent/PT1140937E/pt unknown
- 1999-12-22 HU HU0104827A patent/HUP0104827A3/hu unknown
- 1999-12-22 DK DK99960757T patent/DK1140937T3/da active
- 1999-12-22 KR KR1020017008068A patent/KR100653485B1/ko not_active Expired - Fee Related
- 1999-12-22 CA CA002355712A patent/CA2355712C/en not_active Expired - Fee Related
- 1999-12-22 TR TR2001/02501T patent/TR200102501T2/xx unknown
- 1999-12-22 WO PCT/CA1999/001229 patent/WO2000039143A2/en not_active Ceased
- 1999-12-22 CN CN99816209A patent/CN1117751C/zh not_active Expired - Fee Related
- 1999-12-22 ID IDW00200101622A patent/ID30477A/id unknown
- 1999-12-22 ES ES99960757T patent/ES2209532T3/es not_active Expired - Lifetime
- 1999-12-22 MX MXPA01006425A patent/MXPA01006425A/es not_active Application Discontinuation
- 1999-12-22 BR BR9916849-9A patent/BR9916849A/pt not_active IP Right Cessation
- 1999-12-22 NZ NZ513094A patent/NZ513094A/en unknown
- 1999-12-22 JP JP2000591054A patent/JP2002533470A/ja active Pending
- 1999-12-22 CZ CZ20012352A patent/CZ20012352A3/cs unknown
- 1999-12-22 DE DE69912842T patent/DE69912842T2/de not_active Expired - Lifetime
- 1999-12-22 EP EP99960757A patent/EP1140937B1/en not_active Expired - Lifetime
- 1999-12-22 AT AT99960757T patent/ATE254126T1/de not_active IP Right Cessation
- 1999-12-22 OA OA1200100171A patent/OA11741A/en unknown
- 1999-12-22 US US09/468,813 patent/US6358963B1/en not_active Expired - Fee Related
- 1999-12-22 AP APAP/P/2001/002207A patent/AP2001002207A0/en unknown
- 1999-12-22 AU AU17657/00A patent/AU760875B2/en not_active Ceased
- 1999-12-22 IL IL14386799A patent/IL143867A0/xx unknown
- 1999-12-23 UY UY25878A patent/UY25878A1/es unknown
-
2001
- 2001-06-22 NO NO20013163A patent/NO20013163L/no not_active Application Discontinuation
- 2001-06-29 US US09/893,605 patent/US6545001B2/en not_active Expired - Fee Related
- 2001-07-11 ZA ZA200105702A patent/ZA200105702B/en unknown
-
2003
- 2003-02-28 US US10/375,121 patent/US20040058893A1/en not_active Abandoned
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