JP2012502099A - Ｃ型肝炎の治療のための化合物 - Google Patents

Ｃ型肝炎の治療のための化合物 Download PDF

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Publication number
JP2012502099A
JP2012502099A JP2011526911A JP2011526911A JP2012502099A JP 2012502099 A JP2012502099 A JP 2012502099A JP 2011526911 A JP2011526911 A JP 2011526911A JP 2011526911 A JP2011526911 A JP 2011526911A JP 2012502099 A JP2012502099 A JP 2012502099A
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Japan
Prior art keywords
solvent
alkyl
phenyl
hydrogen
fluorophenyl
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Pending
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JP2011526911A
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English (en)
Japanese (ja)
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JP2012502099A5 (OSRAM
Inventor
リチャード・プラシット
ジョン・エフ・カドウ
ジョン・エイ・ベンダー
ブレット・アール・ベノ
キャサリン・エイ・グラント−ヤング
イン・ハン
ピヤセナ・ヘワワサム
アンドリュー・ニッケル
カイル・イー・パーセラ
カプ−スン・イェウン
ルイス・エス・チュパク
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Bristol Myers Squibb Co
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Bristol Myers Squibb Co
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Publication of JP2012502099A publication Critical patent/JP2012502099A/ja
Publication of JP2012502099A5 publication Critical patent/JP2012502099A5/ja
Pending legal-status Critical Current

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    • 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
    • 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
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
    • 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
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
    • C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
    • C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered

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  • 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)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Virology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Indole Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
JP2011526911A 2008-09-11 2009-09-02 Ｃ型肝炎の治療のための化合物 Pending JP2012502099A (ja)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US9600408P 2008-09-11 2008-09-11
US61/096,004 2008-09-11
PCT/US2009/055648 WO2010030538A2 (en) 2008-09-11 2009-09-02 Compounds for the treatment of hepatitis c

Publications (2)

Publication Number Publication Date
JP2012502099A true JP2012502099A (ja) 2012-01-26
JP2012502099A5 JP2012502099A5 (OSRAM) 2012-10-11

Family

ID=41203516

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2011526911A Pending JP2012502099A (ja) 2008-09-11 2009-09-02 Ｃ型肝炎の治療のための化合物

Country Status (10)

Country Link
US (2) US8198449B2 (OSRAM)
EP (1) EP2331502B1 (OSRAM)
JP (1) JP2012502099A (OSRAM)
KR (1) KR20110056537A (OSRAM)
CN (2) CN102209711B (OSRAM)
AR (1) AR073586A1 (OSRAM)
AU (1) AU2009291993A1 (OSRAM)
MX (1) MX2011002471A (OSRAM)
TW (1) TW201014855A (OSRAM)
WO (1) WO2010030538A2 (OSRAM)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2016500705A (ja) * 2012-11-05 2016-01-14 バイエル・ファルマ・アクティエンゲゼルシャフト アミノ置換イミダゾ［１，２−ａ］ピリジンカルボキサミドおよびその使用
JP2016540745A (ja) * 2013-11-12 2016-12-28 ダウ アグロサイエンシィズ エルエルシー 化合物をフッ素化するための方法
JP2017529401A (ja) * 2014-09-26 2017-10-05 チャーンジョウ インシュヨン ファーマシューティカル カンパニー，リミティド Ｎｓ４ｂ阻害剤としてのベンゾフラン類似体

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EP2493889B1 (en) 2009-10-30 2017-09-06 Janssen Pharmaceutica, N.V. IMIDAZO[1,2-b]PYRIDAZINE DERIVATIVES AND THEIR USE AS PDE10 INHIBITORS
EP2496578A4 (en) 2009-11-05 2013-08-21 Univ Notre Dame Du Lac IMIDAZO [1,2-A] PYRIDINE COMPOUNDS, THEIR SYNTHESIS AND METHODS OF USE THEREOF
FR2953520B1 (fr) * 2009-12-04 2011-11-25 Sanofi Aventis Derives de diphenyl-pyrazolopyridines, leur preparation et leur application en therapeutique
US8324212B2 (en) * 2010-02-25 2012-12-04 Bristol-Myers Squibb Company Compounds for the treatment of hepatitis C
AR080754A1 (es) 2010-03-09 2012-05-09 Janssen Pharmaceutica Nv Derivados de imidazo (1,2-a) pirazina y su uso como inhibidores de pde10
EP2545050B1 (en) * 2010-03-10 2014-08-13 Bristol-Myers Squibb Company Compounds for the treatment of hepatitis c
US8354410B2 (en) 2010-03-11 2013-01-15 Bristol-Meyers Squibb Company Compounds for the treatment of hepatitis C
AR082453A1 (es) * 2010-04-21 2012-12-12 Novartis Ag Compuestos de furopiridina, composiciones farmaceuticas que los contienen y usos de los mismos
US8445497B2 (en) 2010-06-30 2013-05-21 Bristol-Myers Squibb Company Compounds for the treatment of hepatitis C
WO2012051659A1 (en) * 2010-10-20 2012-04-26 Biota Scientific Management Pty Ltd Viral polymerase inhibitors
SG189985A1 (en) 2010-10-26 2013-06-28 Presidio Pharmaceuticals Inc Inhibitors of hepatitis c virus
EP2655362A1 (en) 2010-12-22 2013-10-30 Abbvie Inc. Hepatitis c inhibitors and uses thereof
MX344600B (es) 2011-06-27 2016-12-20 Janssen Pharmaceutica Nv Derivados de 1-aril-4-metil-[1,2,4]triazolo[4,3-a]quinoxalina.
WO2013030750A1 (en) 2011-09-01 2013-03-07 Lupin Limited Antiviral compounds
US9303020B2 (en) 2012-02-08 2016-04-05 Bristol-Myers Squibb Company Compounds for the treatment of hepatitis C
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US9120775B2 (en) 2012-04-11 2015-09-01 Biota Scientific Management Pty Ltd Viral polymerase inhibitors
WO2013163466A1 (en) * 2012-04-25 2013-10-31 Presidio Pharmaceuticals, Inc. Inhibitors of hepatitis c virus
CN102690264B (zh) * 2012-06-20 2014-07-02 泰山医学院 2-苯基-3-取代咪唑并[1,2-a]吡啶类衍生物及其制备方法
HK1206250A1 (en) 2012-06-26 2016-01-08 Janssen Pharmaceutica Nv Combinations comprising pde 2 inhibitors such as 1-aryl-4-methyl-[1,2,4] triazolo [4,3-a] quinoxaline compounds and ped 10 inhibitors for use in the treatment of neurological or metabolic disorders
CN104411314B (zh) 2012-07-09 2017-10-20 詹森药业有限公司 磷酸二酯酶10的抑制剂
US8796305B2 (en) 2012-11-05 2014-08-05 Bayer Pharma Aktiengesellschaft Carboxy-substituted imidazo[1,2-a]pyridinecarboxamides and their use
US8778964B2 (en) 2012-11-05 2014-07-15 Bayer Pharma Aktiengesellschaft Hydroxy-substituted imidazo[1,2-a]-pyridinecarboxamides and their use
US9126998B2 (en) 2012-11-05 2015-09-08 Bayer Pharma AG Amino-substituted imidazo[1,2-a]pyridinecarboxamides and their use
US8871754B2 (en) 2012-11-19 2014-10-28 Irm Llc Compounds and compositions for the treatment of parasitic diseases
DK2925757T3 (en) 2012-11-19 2018-01-15 Novartis Ag Compounds and compositions for the treatment of parasitic diseases
US8962651B2 (en) * 2013-03-13 2015-02-24 Bristol-Myers Squibb Company Compounds for the treatment of hepatitis C
ES2625744T3 (es) 2013-06-04 2017-07-20 Bayer Pharma Aktiengesellschaft Imidazo[1,2-a]piridinas sustituidas con 3-arilo y su uso
CA2939793A1 (en) 2014-02-19 2015-08-27 Bayer Pharma Aktiengesellschaft 3-(pyrimidine-2-yl)imidazo[1,2-a]pyridines
AR099820A1 (es) * 2014-03-21 2016-08-17 Bristol Myers Squibb Co Ciano que contiene compuestos de azabenzofuran para el tratamiento de la hepatitis c
US9920036B2 (en) * 2014-03-21 2018-03-20 Bristol-Myers Squibb Company Cyanoamino (aza)benzofuran compounds for the treatment of hepatitis C
WO2015140199A1 (de) 2014-03-21 2015-09-24 Bayer Pharma Aktiengesellschaft Cyano-substituierte imidazo[1,2-a]pyridincarboxamide und ihre verwendung
EP3137463A1 (de) 2014-05-02 2017-03-08 Bayer Pharma Aktiengesellschaft Enantiomere des n-(2-amino-5-fluor-2-methylpentyl)-8-[(2,6-difluorbenzyl)oxy]-2-methylimidazo[1,2-a]pyridin-3-carboxamids sowie der di- and tri-fluor-derivate zur behandlung von kardiovaskulären erkrankungen
EP3180346A1 (en) * 2014-08-05 2017-06-21 Bristol-Myers Squibb Company Furopyridine compounds for the treatment of hepatitis c
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Title
JPN5011012619; ＥＬＳＮＥＲ　Ｊ: 'ＢＩＣＹＣＬＩＣ　ＭＥＬＡＴＯＮＩＮ　ＲＥＣＥＰＴＯＲ　ＡＧＯＮＩＳＴＳ　ＣＯＮＴＡＩＮＩＮＧ　Ａ　ＲＩＮＧ-ＪＵＮＣＴＩＯＮ　ＮＩＴＲＯＧＥＮ：　以下備考' ＢＩＯＯＲＧＡＮＩＣ　＆　ＭＥＤＩＣＩＮＡＬ　ＣＨＥＭＩＳＴＲＹ Ｖ１４　Ｎ６, 20060315, Ｐ１９４９-１９５８, ＥＬＳＥＶＩＥＲ　ＳＣＩＥＮＣＥ　ＬＴＤ *
JPN5011012620; ＫＡＫＥＨＩ，　ＡＫＩＫＡＺＵ: 'ＰＲＥＰＡＲＡＴＩＯＮ　ＯＦ　ＮＥＷ　ＮＩＴＲＯＧＥＮ-ＢＲＩＤＧＥＤ　ＨＥＴＥＲＯＣＹＣＬＥＳ．　ＸＩＶ．　ＦＵＲＴＨＥＲ　ＩＮＶＥＳＴＩＧＡＴＩＯＮ　以下備考' ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ Ｖ３５　Ｎ１, 1987, Ｐ１５６-１６９ *
JPN5011012621; ＭＩＫＩ，　ＹＡＳＵＹＯＳＨＩ: 'ＡＣＩＤ-ＣＡＴＡＬＹＺＥＤ　ＲＥＡＣＴＩＯＮＳ　ＯＦ　３-（ＨＹＤＲＯＸＹＭＥＴＨＹＬ）-　ＡＮＤ　３-（１-ＨＹＤＲＯＸＹＥＴＨＹＬ）ＰＹＲＡＺＯＬＯ［１，５-ａ］ＰＹＲＩＤＩＮＥＳ' ＪＯＵＲＮＡＬ　ＯＦ　ＨＥＴＥＲＯＣＹＣＬＩＣ　ＣＨＥＭＩＳＴＲＹ Ｖ２６　Ｎ６, 1989, Ｐ１７３９-１７４５ *
JPN5011012622; ＤＩ　ＣＨＩＡＣＣＨＩＯ，　ＡＮＮＡ: 'ＲＥＳＥＡＲＣＨ　ＯＮ　ＨＥＴＥＲＯＣＹＣＬＩＣ　ＣＯＭＰＯＵＮＤＳ，　ＰＡＲＴ　４０．　２-ＰＨＥＮＹＬＩＭＩＤＡＺＯ［１，２-ａ］ＰＹＲＩＤＩＮＥ-以下備考' ＡＲＣＨＩＶ　ＤＥＲ　ＰＨＡＲＭＡＺＩＥ Ｖ３３１　Ｎ９, 1998, Ｐ２７３-２７８ *
JPN5011012623; ＫＡＴＡＧＩＲＩ，　ＮＯＢＵＹＡ: 'ＳＴＵＤＩＥＳ　ＯＦ　ＫＥＴＥＮＥ　ＡＮＤ　ＩＴＳ　ＤＥＲＩＶＡＴＩＶＥＳ．　ＰＡＲＴ　１１９［１］．　ＲＥＡＣＴＩＯＮＳ　ＯＦ　ＨＡＬＯＫＥＴＥＮＥＳ　以下備考' ＪＯＵＲＮＡＬ　ＯＦ　ＨＥＴＥＲＯＣＹＣＬＩＣ　ＣＨＥＭＩＳＴＲＹ Ｖ２１　Ｎ２, 1984, Ｐ４０７-４１２ *
JPN5011012624; ＡＢＩＧＮＥＮＴＥ　Ｅ: 'ＲＥＳＥＡＲＣＨ　ＯＮ　ＨＥＴＥＲＯＣＹＣＬＩＣ　ＣＯＭＰＯＵＮＤＳ．　ＸＸＩＩＩ．　ＰＨＥＮＹＬ　ＤＥＲＩＶＡＴＩＶＥＳ　ＯＦ　ＦＵＳＥＤ　ＩＭＩＤＡＺＯＬＥ　ＳＹＳＴＥＭＳ' ＪＯＵＲＮＡＬ　ＯＦ　ＨＥＴＥＲＯＣＹＣＬＩＣ　ＣＨＥＭＩＳＴＲＹ Ｖ２６, 19891101, Ｐ１８７５-１８８０, ＷＩＬＥＹ-ＢＬＡＣＫＷＥＬＬ　ＰＵＢＬＩＳＨＩＮＧ，　ＩＮＣ *
JPN5011012625; ＴＲＡＰＡＮＩ　Ｇ: 'ＳＹＮＴＨＥＳＩＳ　ＡＮＤ　ＢＩＮＤＩＮＧ　ＡＦＦＩＮＩＴＹ　ＯＦ　２-ＰＨＥＮＹＬＩＭＩＤＡＺＯ［１，２-ａ］ＰＹＲＩＤＩＮＥ　ＤＥＲＩＶＡＴＩＶＥＳ　以下備考' ＪＯＵＲＮＡＬ　ＯＦ　ＭＥＤＩＣＩＮＡＬ　ＣＨＥＭＩＳＴＲＹ Ｖ４０, 19970101, Ｐ３１０９-３１１８, ＡＭＥＲＩＣＡＮ　ＣＨＥＭＩＣＡＬ　ＳＯＣＩＥＴＹ *
JPN7014000590; ＳＴＮ　ＯＮ　ＴＨＥ　ＷＥＢ，　ＦＩＬＥ　ＲＥＧＩＳＴＲＹ，　ＲＮ＝１０２７１８０-２０-６，９５９５７７-６８-５，８８７５９０-０５-８，８７３９４３-８２-９ *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2016500705A (ja) * 2012-11-05 2016-01-14 バイエル・ファルマ・アクティエンゲゼルシャフト アミノ置換イミダゾ［１，２−ａ］ピリジンカルボキサミドおよびその使用
JP2016540745A (ja) * 2013-11-12 2016-12-28 ダウ アグロサイエンシィズ エルエルシー 化合物をフッ素化するための方法
JP2017529401A (ja) * 2014-09-26 2017-10-05 チャーンジョウ インシュヨン ファーマシューティカル カンパニー，リミティド Ｎｓ４ｂ阻害剤としてのベンゾフラン類似体
US10100027B2 (en) 2014-09-26 2018-10-16 Changzhou Yinsheng Pharmaceutical Co., Ltd. Benzofuran analogue as NS4B inhibitor

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US20100063068A1 (en) 2010-03-11
KR20110056537A (ko) 2011-05-30
WO2010030538A2 (en) 2010-03-18
US20120232099A1 (en) 2012-09-13
MX2011002471A (es) 2011-04-05
US8198449B2 (en) 2012-06-12
CN102209711B (zh) 2014-06-18
AU2009291993A1 (en) 2010-03-18
TW201014855A (en) 2010-04-16
AR073586A1 (es) 2010-11-17
EP2331502A2 (en) 2011-06-15
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