AR076460A1 - Antagonistas del receptor cxcr3 - Google Patents
Antagonistas del receptor cxcr3Info
- Publication number
- AR076460A1 AR076460A1 ARP100101401A ARP100101401A AR076460A1 AR 076460 A1 AR076460 A1 AR 076460A1 AR P100101401 A ARP100101401 A AR P100101401A AR P100101401 A ARP100101401 A AR P100101401A AR 076460 A1 AR076460 A1 AR 076460A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- alkoxy
- cycloalkyl
- nr9r10
- heteroaryl
- Prior art date
Links
- 102100028990 C-X-C chemokine receptor type 3 Human genes 0.000 title 1
- 101000916050 Homo sapiens C-X-C chemokine receptor type 3 Proteins 0.000 title 1
- 239000005557 antagonist Substances 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 8
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 150000002367 halogens Chemical class 0.000 abstract 4
- 125000001072 heteroaryl group Chemical group 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 3
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 abstract 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000000304 alkynyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 125000004043 oxo group Chemical group O=* 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 abstract 1
- -1 -S (O) mCH3 Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 abstract 1
- 208000037765 diseases and disorders Diseases 0.000 abstract 1
- 125000005553 heteroaryloxy group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Abstract
Y sales farmacéuticamente aceptables de Ios mismos, en la que R1 a R6, A, B, X, Y y n son como se definen en la presente. Composiciones farmacéuticas que comprenden estos compuestos, a métodos para usar estos compuestos en el tratamiento de diversas enfermedades y trastornos. Reivindicacion 1: Un compuesto caracterizado porque tiene la formula (1): en la que: A es C o N; B es C o N; X es -NHC(O)-, -N(CH3)C(O)-, -NH- o está ausente; Y es -C(O)NH- o -NHC(O)-; R1 es H, -CN, halogeno, -CF3, -OCF3, alquilo C1-3, alcoxi C1-3, -S(O)mCH3, amino, mono- o dimetilamino, -NHC(O)alquilo C1-3, -NO2 -C(O)NH2, -C(O)NHalquilo C1-3 o -C(O)alquilo C1-3; R2 es arilo, heteroarilo o cicloalquilo C3-10, cada uno opcionalmente sustituido con de uno a tres R7; R3 es heteroarilo, heterociclilo, arilo o cicloalquilo C3-10, cada uno opcionalmente sustituido con de uno a tres R8; R4 es H o alquilo C1-6; cada uno de R5 y R6 se selecciona independientemente entre H, alquilo C1-2 y fenilo; o R5 y R6 pueden unirse para formar un puente etilo; R7 es -OH, oxo, hidroxialquilo C1-6, halogeno, -(CH2)m-CN, nitro, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-10, alcoxi C1-6, fenoxi, heteroariloxi, alcoxicarbonilo C1-6, carboxilo, -C(O)alquilo C1-6, -(CH2)m-NR9R10, -S(O)malquilo C1-6, -NHS(O)2alquhlo C1-6, NR9C(O)alquilo C1-6, -S(O)2NR9R10, -C(O)NR9R10 heterociclilo, heteroarilo, fenilo o bencilo, donde cada alquilo, alquenilo, alquinilo o alcoxi está opcionalmente parcial o totalmente halogenado y cada heterociclo, heteroarilo, fenilo o bencilo de dicho R7 está opcionalmente sustituido con de uno a tres alquilo C1-6, alcoxi C1-6(CH2)m, halogeno, -CN, -CF3, acilo C1-6, -NR9R10, -C(O)NR9R10, -OH, hidroxialquilo C1-6 o -S(O)malquilo C1-6; R8 es alquilo C1-6, alquenilo C2-6, alquinilo C2-6, carboxilo, cicloalquilo C3-10, alcoxi C1-6, halogeno, oxo o fenilo, donde cada alquilo, alquenilo, alquinilo, cicloalquilo o alcoxi está opcionalmente parcial o totalmente halogenado; R9 y R10 se seleccionan independientemente entre hidrogeno, alquilo C1-6, acilo C1-6, cicloalquilo C3-10, hidroxialquilo C1-6, alquil C1-6-alcoxi C1-6, alquilsulfonilo C1-6 y alcoxicarbonilo C1-6; m es 0-2; n es 1 o 2; -------- es un enlace sencillo si A es N o un enlace sencillo o doble enlace si A es C; o una sal farmacéuticamente aceptable del mismo.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17286909P | 2009-04-27 | 2009-04-27 | |
| US31735110P | 2010-03-25 | 2010-03-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR076460A1 true AR076460A1 (es) | 2011-06-15 |
Family
ID=42272001
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP100101401A AR076460A1 (es) | 2009-04-27 | 2010-04-26 | Antagonistas del receptor cxcr3 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8362249B2 (es) |
| EP (1) | EP2424858B1 (es) |
| JP (1) | JP5741574B2 (es) |
| AR (1) | AR076460A1 (es) |
| TW (1) | TW201103933A (es) |
| UY (1) | UY32574A (es) |
| WO (1) | WO2010126851A1 (es) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2330894B8 (en) | 2008-09-03 | 2017-04-19 | BioMarin Pharmaceutical Inc. | Compositions including 6-aminohexanoic acid derivatives as hdac inhibitors |
| JP5807971B2 (ja) * | 2009-04-27 | 2015-11-10 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃｘｃｒ３受容体アンタゴニスト |
| JP2011057661A (ja) * | 2009-08-14 | 2011-03-24 | Bayer Cropscience Ag | 殺虫性カルボキサミド類 |
| WO2011084985A1 (en) * | 2010-01-07 | 2011-07-14 | Boehringer Ingelheim International Gmbh | Cxcr3 receptor antagonists |
| CA2828524C (en) | 2011-02-28 | 2020-01-07 | Repligen Corporation | Histone deacetylase inhibitors |
| US10059723B2 (en) | 2011-02-28 | 2018-08-28 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| US8957066B2 (en) | 2011-02-28 | 2015-02-17 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| EP2508511A1 (en) | 2011-04-07 | 2012-10-10 | Laboratoire Biodim | Inhibitors of viral replication, their process of preparation and their therapeutical uses |
| CN104093715B (zh) | 2012-02-02 | 2017-04-26 | 埃科特莱茵药品有限公司 | 4‑(苯并咪唑‑2‑基)‑噻唑化合物及相关氮杂衍生物 |
| JP6503338B2 (ja) | 2013-03-15 | 2019-04-17 | バイオマリン ファーマシューティカル インコーポレイテッド | Ｈｄａｃ阻害剤 |
| WO2014182673A1 (en) * | 2013-05-07 | 2014-11-13 | Arena Pharmaceuticals, Inc. | Modulators of the g protein-coupled mas receptor and the treatment of disorders related thereto |
| WO2014182688A1 (en) * | 2013-05-07 | 2014-11-13 | Arena Pharmaceuticals, Inc. | Modulators of the g protein-coupled mas receptor and the treatment of disorders related thereto |
| US9663529B2 (en) | 2013-07-02 | 2017-05-30 | Bristol-Myers Squibb Company | Tricyclic pyrido-carboxamide derivatives as rock inhibitors |
| JP6434968B2 (ja) | 2013-07-02 | 2018-12-05 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | Ｒｏｃｋ阻害剤としての三環式ピリド−カルボキサミド誘導体 |
| WO2015011099A1 (en) | 2013-07-22 | 2015-01-29 | Actelion Pharmaceuticals Ltd | 1-(piperazin-1-yl)-2-([1,2,4]triazol-1-yl)-ethanone derivatives |
| AR099789A1 (es) | 2014-03-24 | 2016-08-17 | Actelion Pharmaceuticals Ltd | Derivados de 8-(piperazin-1-il)-1,2,3,4-tetrahidro-isoquinolina |
| DK3174868T3 (da) * | 2014-08-01 | 2021-11-08 | Nuevolution As | Forbindelser, der er aktive mod bromodomæner |
| TWI689497B (zh) * | 2014-09-04 | 2020-04-01 | 南北兄弟藥業投資有限公司 | 芳雜環類衍生物及其在藥物中的應用 |
| AR103399A1 (es) * | 2015-01-15 | 2017-05-10 | Actelion Pharmaceuticals Ltd | Derivados de (r)-2-metil-piperazina como moduladores del receptor cxcr3 |
| TR201900680T4 (tr) | 2015-01-15 | 2019-02-21 | Idorsia Pharmaceuticals Ltd | CXCR3 Reseptör modülatörleri olarak hidroksialkil- piperazin türevleri. |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003236500B9 (en) * | 2002-06-12 | 2009-07-02 | Chemocentryx, Inc. | 1-aryl-4-substituted piperazine derivatives for use as CCR1 antagonists for the treatment of inflammation and immune disorders |
| US20050256130A1 (en) * | 2002-06-12 | 2005-11-17 | Chemocentryx, Inc. | Substituted piperazines |
| EP2308848A1 (en) * | 2003-02-03 | 2011-04-13 | Janssen Pharmaceutica NV | Quinoline-derived amide modulators of vanilloid VR1 receptor |
| EA017278B9 (ru) * | 2005-06-22 | 2013-01-30 | Кемосентрикс, Инк. | Соединения азаиндазола и способы применения |
| WO2007100610A2 (en) * | 2006-02-23 | 2007-09-07 | Merck & Co., Inc. | Pyridine, pyrimidine and pyrazine derivatives as cxcr3 receptor modulators |
| JP5286646B2 (ja) * | 2006-04-19 | 2013-09-11 | トヨタ自動車株式会社 | スルホン基含有モノマーの重合方法 |
| EP2009005A4 (en) * | 2006-04-19 | 2010-06-02 | Astellas Pharma Inc | AZOLECARBOXAMIDE DERIVATIVE |
| US20090099201A1 (en) * | 2007-05-22 | 2009-04-16 | David Robert Bolin | Diacylglycerol Acyltransferase Inhibitors |
| JO2972B1 (en) * | 2007-06-08 | 2016-03-15 | جانسين فارماسوتيكا ان. في | Piperidine / piperazine derivatives |
| JP5807971B2 (ja) * | 2009-04-27 | 2015-11-10 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃｘｃｒ３受容体アンタゴニスト |
-
2010
- 2010-04-21 US US12/764,136 patent/US8362249B2/en active Active
- 2010-04-23 UY UY0001032574A patent/UY32574A/es not_active Application Discontinuation
- 2010-04-26 TW TW099113117A patent/TW201103933A/zh unknown
- 2010-04-26 AR ARP100101401A patent/AR076460A1/es unknown
- 2010-04-27 EP EP10715474.2A patent/EP2424858B1/en active Active
- 2010-04-27 WO PCT/US2010/032477 patent/WO2010126851A1/en active Application Filing
- 2010-04-27 JP JP2012507474A patent/JP5741574B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP2424858A1 (en) | 2012-03-07 |
| US8362249B2 (en) | 2013-01-29 |
| WO2010126851A1 (en) | 2010-11-04 |
| TW201103933A (en) | 2011-02-01 |
| UY32574A (es) | 2010-11-30 |
| JP5741574B2 (ja) | 2015-07-01 |
| EP2424858B1 (en) | 2014-05-14 |
| JP2012525335A (ja) | 2012-10-22 |
| US20100273781A1 (en) | 2010-10-28 |
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