JP2004525184A5 - - Google Patents
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- Publication number
- JP2004525184A5 JP2004525184A5 JP2002581419A JP2002581419A JP2004525184A5 JP 2004525184 A5 JP2004525184 A5 JP 2004525184A5 JP 2002581419 A JP2002581419 A JP 2002581419A JP 2002581419 A JP2002581419 A JP 2002581419A JP 2004525184 A5 JP2004525184 A5 JP 2004525184A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- piperazin
- ylmethyl
- quinoline
- amide
- 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 claims 23
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 239000012453 solvate Substances 0.000 claims 8
- 125000005843 halogen group Chemical group 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- -1 hydroxy, amino Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 229940124530 sulfonamide Drugs 0.000 claims 2
- 150000003456 sulfonamides Chemical class 0.000 claims 2
- 208000024891 symptom Diseases 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- NUXLBIXRPWTDPR-UHFFFAOYSA-N 2-(2-fluorophenyl)-3-[(3-oxopiperazin-1-yl)methyl]quinoline-4-carboxylic acid Chemical compound C=1C=CC=C(F)C=1C1=NC2=CC=CC=C2C(C(=O)O)=C1CN1CCNC(=O)C1 NUXLBIXRPWTDPR-UHFFFAOYSA-N 0.000 claims 1
- IFLOZZGCYMGFBK-UHFFFAOYSA-N 2-(4-fluorophenyl)-3-[(3-oxopiperazin-1-yl)methyl]quinoline-4-carboxylic acid Chemical compound C=1C=C(F)C=CC=1C1=NC2=CC=CC=C2C(C(=O)O)=C1CN1CCNC(=O)C1 IFLOZZGCYMGFBK-UHFFFAOYSA-N 0.000 claims 1
- GZAINRLYQOVLRP-UHFFFAOYSA-N 2-[cyano(nitro)amino]-2-oxoacetic acid Chemical compound [N+](=O)([O-])N(C(=O)C(=O)O)C#N GZAINRLYQOVLRP-UHFFFAOYSA-N 0.000 claims 1
- WQCHHMUICZGFAS-UHFFFAOYSA-N 2-phenyl-n-(2-phenylpropan-2-yl)-3-(piperazin-1-ylmethyl)quinoline-4-carboxamide Chemical compound C=1C=CC=CC=1C(C)(C)NC(=O)C(C1=CC=CC=C1N=C1C=2C=CC=CC=2)=C1CN1CCNCC1 WQCHHMUICZGFAS-UHFFFAOYSA-N 0.000 claims 1
- JIIFVNDMAANPOP-NRFANRHFSA-N 2-phenyl-n-[(1s)-1-phenylethyl]-3-(piperazin-1-ylmethyl)quinoline-4-carboxamide Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(=O)C(C1=CC=CC=C1N=C1C=2C=CC=CC=2)=C1CN1CCNCC1 JIIFVNDMAANPOP-NRFANRHFSA-N 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- JFHYQPLKCXUQBU-UHFFFAOYSA-N 3-[(3-oxopiperazin-1-yl)methyl]-2-[4-(trifluoromethyl)phenyl]quinoline-4-carboxylic acid Chemical compound C=1C=C(C(F)(F)F)C=CC=1C1=NC2=CC=CC=C2C(C(=O)O)=C1CN1CCNC(=O)C1 JFHYQPLKCXUQBU-UHFFFAOYSA-N 0.000 claims 1
- CVSSIQTWROPMMS-UHFFFAOYSA-N 3-[(3-oxopiperazin-1-yl)methyl]-2-phenyl-7-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound C=1C=CC=CC=1C1=NC2=CC(C(F)(F)F)=CC=C2C(C(=O)O)=C1CN1CCNC(=O)C1 CVSSIQTWROPMMS-UHFFFAOYSA-N 0.000 claims 1
- XKBUSWBSGIWEQN-VWLOTQADSA-N 3-[(3-oxopiperazin-1-yl)methyl]-2-phenyl-n-[(1s)-1-phenylpropyl]quinoline-4-carboxamide Chemical compound N([C@@H](CC)C=1C=CC=CC=1)C(=O)C(C1=CC=CC=C1N=C1C=2C=CC=CC=2)=C1CN1CCNC(=O)C1 XKBUSWBSGIWEQN-VWLOTQADSA-N 0.000 claims 1
- DUJALBZYHPPJIB-SANMLTNESA-N 3-[(4-benzyl-3-oxopiperazin-1-yl)methyl]-n-[(1s)-1-cyclohexylethyl]-2-phenylquinoline-4-carboxamide Chemical compound N([C@@H](C)C1CCCCC1)C(=O)C(C1=CC=CC=C1N=C1C=2C=CC=CC=2)=C1CN(CC1=O)CCN1CC1=CC=CC=C1 DUJALBZYHPPJIB-SANMLTNESA-N 0.000 claims 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- ZKUWYZFLWYJWRM-FQEVSTJZSA-N 6-chloro-n-[(1s)-1-cyclohexylethyl]-2-phenyl-3-(piperazin-1-ylmethyl)quinoline-4-carboxamide Chemical compound N([C@@H](C)C1CCCCC1)C(=O)C(C1=CC(Cl)=CC=C1N=C1C=2C=CC=CC=2)=C1CN1CCNCC1 ZKUWYZFLWYJWRM-FQEVSTJZSA-N 0.000 claims 1
- JWFULDDAJMQUFY-IBGZPJMESA-N 7-chloro-n-[(1s)-1-cyclohexylethyl]-3-[(3-oxopiperazin-1-yl)methyl]-2-phenylquinoline-4-carboxamide Chemical compound N([C@@H](C)C1CCCCC1)C(=O)C(C1=CC=C(Cl)C=C1N=C1C=2C=CC=CC=2)=C1CN1CCNC(=O)C1 JWFULDDAJMQUFY-IBGZPJMESA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004990 dihydroxyalkyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- IAROSRSCHWUJPN-UHFFFAOYSA-N n-(2-cyclohexylpropan-2-yl)-2-phenyl-3-(piperazin-1-ylmethyl)quinoline-4-carboxamide Chemical compound C1CCCCC1C(C)(C)NC(=O)C(C1=CC=CC=C1N=C1C=2C=CC=CC=2)=C1CN1CCNCC1 IAROSRSCHWUJPN-UHFFFAOYSA-N 0.000 claims 1
- SUCQKPUTZDUCKO-OAQYLSRUSA-N n-[(1r)-1-cyclohexylethyl]-2-phenyl-3-(piperazin-1-ylmethyl)quinoline-4-carboxamide Chemical compound N([C@H](C)C1CCCCC1)C(=O)C(C1=CC=CC=C1N=C1C=2C=CC=CC=2)=C1CN1CCNCC1 SUCQKPUTZDUCKO-OAQYLSRUSA-N 0.000 claims 1
- FRLOMTKENUJIBA-FQEVSTJZSA-N n-[(1s)-1-(3-hydroxyphenyl)ethyl]-2-phenyl-3-(piperazin-1-ylmethyl)quinoline-4-carboxamide Chemical compound N([C@@H](C)C=1C=C(O)C=CC=1)C(=O)C(C1=CC=CC=C1N=C1C=2C=CC=CC=2)=C1CN1CCNCC1 FRLOMTKENUJIBA-FQEVSTJZSA-N 0.000 claims 1
- IYFXEBXJKPDKKE-NRFANRHFSA-N n-[(1s)-1-(3-methoxyphenyl)ethyl]-2-phenyl-3-(piperazin-1-ylmethyl)quinoline-4-carboxamide Chemical compound COC1=CC=CC([C@H](C)NC(=O)C=2C3=CC=CC=C3N=C(C=2CN2CCNCC2)C=2C=CC=CC=2)=C1 IYFXEBXJKPDKKE-NRFANRHFSA-N 0.000 claims 1
- PEWFAHXSQSTDSV-FQEVSTJZSA-N n-[(1s)-1-(4-hydroxyphenyl)ethyl]-2-phenyl-3-(piperazin-1-ylmethyl)quinoline-4-carboxamide Chemical compound N([C@@H](C)C=1C=CC(O)=CC=1)C(=O)C(C1=CC=CC=C1N=C1C=2C=CC=CC=2)=C1CN1CCNCC1 PEWFAHXSQSTDSV-FQEVSTJZSA-N 0.000 claims 1
- ACKMAOFGHHZZPA-NRFANRHFSA-N n-[(1s)-1-(4-methoxyphenyl)ethyl]-2-phenyl-3-(piperazin-1-ylmethyl)quinoline-4-carboxamide Chemical compound C1=CC(OC)=CC=C1[C@H](C)NC(=O)C(C1=CC=CC=C1N=C1C=2C=CC=CC=2)=C1CN1CCNCC1 ACKMAOFGHHZZPA-NRFANRHFSA-N 0.000 claims 1
- DQYRFBCPAJIZCP-FQEVSTJZSA-N n-[(1s)-1-cyclohexylethyl]-3-[(2-oxopiperazin-1-yl)methyl]-2-phenylquinoline-4-carboxamide Chemical compound N([C@@H](C)C1CCCCC1)C(=O)C(C1=CC=CC=C1N=C1C=2C=CC=CC=2)=C1CN1CCNCC1=O DQYRFBCPAJIZCP-FQEVSTJZSA-N 0.000 claims 1
- PNHQPBUQYXNCBZ-IBGZPJMESA-N n-[(1s)-1-cyclohexylethyl]-3-[(3-oxopiperazin-1-yl)methyl]-2-phenyl-6-(trifluoromethyl)quinoline-4-carboxamide Chemical compound N([C@@H](C)C1CCCCC1)C(=O)C(C1=CC(=CC=C1N=C1C=2C=CC=CC=2)C(F)(F)F)=C1CN1CCNC(=O)C1 PNHQPBUQYXNCBZ-IBGZPJMESA-N 0.000 claims 1
- HSGBITFGUJIXDH-FQEVSTJZSA-N n-[(1s)-1-cyclohexylethyl]-3-[(3-oxopiperazin-1-yl)methyl]-2-phenylquinoline-4-carboxamide Chemical compound N([C@@H](C)C1CCCCC1)C(=O)C(C1=CC=CC=C1N=C1C=2C=CC=CC=2)=C1CN1CCNC(=O)C1 HSGBITFGUJIXDH-FQEVSTJZSA-N 0.000 claims 1
- MPMGBYSOQNAFLN-SFHVURJKSA-N n-[(1s)-1-cyclohexylethyl]-3-[(3-oxopiperazin-1-yl)methyl]-2-thiophen-2-ylquinoline-4-carboxamide Chemical compound N([C@@H](C)C1CCCCC1)C(=O)C(C1=CC=CC=C1N=C1C=2SC=CC=2)=C1CN1CCNC(=O)C1 MPMGBYSOQNAFLN-SFHVURJKSA-N 0.000 claims 1
- JECPAFXTVHXXJS-FQEVSTJZSA-N n-[(1s)-1-cyclohexylethyl]-6-fluoro-2-phenyl-3-(piperazin-1-ylmethyl)quinoline-4-carboxamide Chemical compound N([C@@H](C)C1CCCCC1)C(=O)C(C1=CC(F)=CC=C1N=C1C=2C=CC=CC=2)=C1CN1CCNCC1 JECPAFXTVHXXJS-FQEVSTJZSA-N 0.000 claims 1
- UBDDQHDOCWVJLR-IBGZPJMESA-N n-[(1s)-1-cyclohexylethyl]-6-fluoro-3-[(3-oxopiperazin-1-yl)methyl]-2-phenylquinoline-4-carboxamide Chemical compound N([C@@H](C)C1CCCCC1)C(=O)C(C1=CC(F)=CC=C1N=C1C=2C=CC=CC=2)=C1CN1CCNC(=O)C1 UBDDQHDOCWVJLR-IBGZPJMESA-N 0.000 claims 1
- RCBHNAIJPNNROD-IBGZPJMESA-N n-[(1s)-1-cyclohexylethyl]-7-fluoro-3-[(3-oxopiperazin-1-yl)methyl]-2-phenylquinoline-4-carboxamide Chemical compound N([C@@H](C)C1CCCCC1)C(=O)C(C1=CC=C(F)C=C1N=C1C=2C=CC=CC=2)=C1CN1CCNC(=O)C1 RCBHNAIJPNNROD-IBGZPJMESA-N 0.000 claims 1
- UNZWYDXOJKALCE-IBGZPJMESA-N n-[(1s)-1-cyclohexylethyl]-8-fluoro-3-[(3-oxopiperazin-1-yl)methyl]-2-phenylquinoline-4-carboxamide Chemical compound N([C@@H](C)C1CCCCC1)C(=O)C(C1=CC=CC(F)=C1N=C1C=2C=CC=CC=2)=C1CN1CCNC(=O)C1 UNZWYDXOJKALCE-IBGZPJMESA-N 0.000 claims 1
- ZMSCZDVVVBSCSB-LJAQVGFWSA-N n-[(1s)-2-methyl-1-phenylpropyl]-3-[(3-oxopiperazin-1-yl)methyl]-2-phenylquinoline-4-carboxamide Chemical compound N([C@@H](C(C)C)C=1C=CC=CC=1)C(=O)C(C1=CC=CC=C1N=C1C=2C=CC=CC=2)=C1CN1CCNC(=O)C1 ZMSCZDVVVBSCSB-LJAQVGFWSA-N 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0109123.0A GB0109123D0 (en) | 2001-04-11 | 2001-04-11 | Novel compounds |
| GB0205649A GB0205649D0 (en) | 2002-03-11 | 2002-03-11 | Novel compounds |
| PCT/EP2002/004070 WO2002083664A1 (en) | 2001-04-11 | 2002-04-11 | 3-substituted quinoline-4-carboxamide derivatives as nk-3 and nk-2 receptor antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004525184A JP2004525184A (ja) | 2004-08-19 |
| JP2004525184A5 true JP2004525184A5 (enExample) | 2005-12-22 |
Family
ID=26245967
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002581419A Pending JP2004525184A (ja) | 2001-04-11 | 2002-04-11 | Ｎｋ−３およびｎｋ−２受容体アンタゴニストとしての３−置換キノリン−４−カルボキサミド誘導体 |
| JP2002581418A Pending JP2004525183A (ja) | 2001-04-11 | 2002-04-11 | Ｎｋ−３およびｎｋ−２受容体アンタゴニストとしてのキノリン−４−カルボキサミド誘導体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002581418A Pending JP2004525183A (ja) | 2001-04-11 | 2002-04-11 | Ｎｋ−３およびｎｋ−２受容体アンタゴニストとしてのキノリン−４−カルボキサミド誘導体 |
Country Status (7)
| Country | Link |
|---|---|
| US (5) | US20040152726A1 (enExample) |
| EP (3) | EP1377567B1 (enExample) |
| JP (2) | JP2004525184A (enExample) |
| AT (2) | ATE318266T1 (enExample) |
| DE (2) | DE60209362T2 (enExample) |
| ES (2) | ES2259096T3 (enExample) |
| WO (2) | WO2002083663A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITMI20031292A1 (it) * | 2003-06-25 | 2004-12-26 | Nikem Research Srl | Derivati biciclici nk-2 antagonisti selettivi. |
| US20070060593A1 (en) * | 2003-06-25 | 2007-03-15 | Kerns Jeffrey K | 4-Carboxamido quinoline derivatives for use as nk-2 and nk-3 |
| AU2005238388B2 (en) | 2004-04-28 | 2011-08-25 | Takeda Pharmaceutical Company Limited | Fused quinoline derivative and use thereof |
| GB0417702D0 (en) * | 2004-08-09 | 2004-09-08 | Merck Sharp & Dohme | New uses |
| GB0425076D0 (en) * | 2004-11-12 | 2004-12-15 | Smithkline Beecham Corp | Novel compounds |
| AU2006253054A1 (en) * | 2005-06-03 | 2006-12-07 | Astrazeneca Ab | Quinoline derivatives as NK3 anatgonists |
| MX2007015607A (es) * | 2005-06-23 | 2008-02-25 | Astrazeneca Ab | Esteres de quinolin 3-sulfonato como moduladores del receptor de nk3. |
| GB0515580D0 (en) | 2005-07-29 | 2005-09-07 | Merck Sharp & Dohme | Therapeutic compounds |
| AR057130A1 (es) | 2005-09-21 | 2007-11-14 | Astrazeneca Ab | Quinolinas de alquilsulfoxido y una composicion farmaceutica |
| EP1940795A1 (en) * | 2005-09-21 | 2008-07-09 | AstraZeneca AB | N-oxo-heterocycle and n-oxo-alkyl quinoline-4-carboxamides as nk-3 receptor ligands |
| AU2008231384B2 (en) * | 2007-03-23 | 2011-09-15 | Amgen Inc. | Heterocyclic compounds and their use |
| WO2008153027A1 (ja) * | 2007-06-11 | 2008-12-18 | Takeda Pharmaceutical Company Limited | ピロロキノリン誘導体およびその用途 |
| PE20091093A1 (es) | 2007-12-03 | 2009-08-25 | Takeda Pharmaceutical | Compuesto heterociclico que contiene nitrogeno y su uso |
| WO2009128262A1 (ja) * | 2008-04-15 | 2009-10-22 | 武田薬品工業株式会社 | キノロン誘導体およびその用途 |
| PL2342182T3 (pl) * | 2008-09-15 | 2013-04-30 | H Lundbeck As | Pochodne izochinolinonu jako antagoniści NK3 |
| US8242134B2 (en) | 2008-09-15 | 2012-08-14 | H. Lundbeck A/S | Isoquinolinone derivatives as NK3 antagonists |
| USRE49686E1 (en) | 2008-09-19 | 2023-10-10 | Takeda Pharmaceutical Company Limited | Nitrogen-containing heterocyclic compound and use of same |
| CN102584852B (zh) * | 2011-12-30 | 2014-08-13 | 厦门大学 | 真菌代谢产物桥南霉素及其制备方法和应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL186665B1 (pl) * | 1994-05-27 | 2004-02-27 | Smithkline Beecham Spa | Pochodne chinoliny jako antagoniści receptorów NKtachykininy, sposób ich wytwarzania, kompozycja farmaceutyczna zawierająca pochodne chinoliny oraz ich zastosowanie |
| EP0876347B1 (en) * | 1995-11-24 | 2005-03-02 | GlaxoSmithKline S.p.A. | Quinoline derivatives |
| AR004735A1 (es) * | 1995-11-24 | 1999-03-10 | Smithkline Beecham Spa | Quinoleina 4-amido sustituida, un procedimiento para su preparacion, una composicion farmaceutica que los contiene y el uso de los mismos para lapreparacion de un medicamento. |
| IL133036A0 (en) * | 1997-05-23 | 2001-03-19 | Smithkline Beecham Spa | Quinoline-4-carboxamide derivatives as nk-2 and nk-3 receptor antagonists |
| BR9915475A (pt) * | 1998-11-20 | 2001-12-18 | Smithkline Beecham Spa | Derivados da quinolina-4-carboxamida comoantagonistas dos receptores de nk-3 e nk-2 |
| GB9825554D0 (en) * | 1998-11-20 | 1999-01-13 | Smithkline Beecham Spa | Novel Compounds |
-
2002
- 2002-04-11 WO PCT/EP2002/004066 patent/WO2002083663A1/en not_active Ceased
- 2002-04-11 EP EP02735247A patent/EP1377567B1/en not_active Expired - Lifetime
- 2002-04-11 DE DE60209362T patent/DE60209362T2/de not_active Expired - Fee Related
- 2002-04-11 ES ES02761911T patent/ES2259096T3/es not_active Expired - Lifetime
- 2002-04-11 EP EP02761911A patent/EP1385839B1/en not_active Expired - Lifetime
- 2002-04-11 AT AT02761911T patent/ATE318266T1/de not_active IP Right Cessation
- 2002-04-11 JP JP2002581419A patent/JP2004525184A/ja active Pending
- 2002-04-11 ES ES02735247T patent/ES2254688T3/es not_active Expired - Lifetime
- 2002-04-11 AT AT02735247T patent/ATE313539T1/de not_active IP Right Cessation
- 2002-04-11 WO PCT/EP2002/004070 patent/WO2002083664A1/en not_active Ceased
- 2002-04-11 EP EP06075240A patent/EP1659120A1/en not_active Withdrawn
- 2002-04-11 JP JP2002581418A patent/JP2004525183A/ja active Pending
- 2002-04-11 US US10/474,542 patent/US20040152726A1/en not_active Abandoned
- 2002-04-11 DE DE60208178T patent/DE60208178T2/de not_active Expired - Fee Related
-
2005
- 2005-04-06 US US11/100,256 patent/US20050176762A1/en not_active Abandoned
-
2006
- 2006-06-28 US US11/426,956 patent/US20060229315A1/en not_active Abandoned
-
2007
- 2007-03-13 US US11/685,380 patent/US20070161647A1/en not_active Abandoned
- 2007-06-26 US US11/768,338 patent/US20070259882A1/en not_active Abandoned
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