JP5746972B2 - ホスホジエステラーゼ10阻害剤としてのピラジン化合物 - Google Patents

ホスホジエステラーゼ10阻害剤としてのピラジン化合物 Download PDF

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JP5746972B2
JP5746972B2 JP2011536567A JP2011536567A JP5746972B2 JP 5746972 B2 JP5746972 B2 JP 5746972B2 JP 2011536567 A JP2011536567 A JP 2011536567A JP 2011536567 A JP2011536567 A JP 2011536567A JP 5746972 B2 JP5746972 B2 JP 5746972B2
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benzo
pyrazin
alkyl
phenyl
yloxy
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JP2012508776A (ja
JP2012508776A5 (https=
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アレン,ジエニフアー・アール
ブルボー,マシユー・ピー
チエン,ニン
フー,エツサ
クンツ,ロクサーヌ
ラムフエルト,シヤノン
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アムジエン・インコーポレーテツド
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic 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
    • C07D403/12Heterocyclic 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 chain containing hetero atoms as chain links
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/4965Non-condensed pyrazines
    • A61K31/497Non-condensed pyrazines containing further heterocyclic rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/14Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/14Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16Anti-Parkinson drugs
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/18Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/24Antidepressants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/28Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/30Drugs for disorders of the nervous system for treating abuse or dependence
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/30Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/36Opioid-abuse
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/04Anorexiants; Antiobesity agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/08Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic 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
    • C07D401/14Heterocyclic 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 three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D407/00Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/14Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic 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
    • C07D417/14Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic 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
    • C07D471/02Heterocyclic 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
    • C07D471/04Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Psychiatry (AREA)
  • Diabetes (AREA)
  • Addiction (AREA)
  • Hematology (AREA)
  • Psychology (AREA)
  • Obesity (AREA)
  • Emergency Medicine (AREA)
  • Child & Adolescent Psychology (AREA)
  • Endocrinology (AREA)
  • Pain & Pain Management (AREA)
  • Hospice & Palliative Care (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
JP2011536567A 2008-11-14 2009-11-16 ホスホジエステラーゼ10阻害剤としてのピラジン化合物 Expired - Fee Related JP5746972B2 (ja)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US11456708P 2008-11-14 2008-11-14
US61/114,567 2008-11-14
US16621209P 2009-04-02 2009-04-02
US61/166,212 2009-04-02
PCT/US2009/064637 WO2010057121A1 (en) 2008-11-14 2009-11-16 Pyrazine compounds as phosphodiesterase 10 inhibitors

Publications (3)

Publication Number Publication Date
JP2012508776A JP2012508776A (ja) 2012-04-12
JP2012508776A5 JP2012508776A5 (https=) 2014-12-04
JP5746972B2 true JP5746972B2 (ja) 2015-07-08

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JP2011536567A Expired - Fee Related JP5746972B2 (ja) 2008-11-14 2009-11-16 ホスホジエステラーゼ10阻害剤としてのピラジン化合物

Country Status (30)

Country Link
US (4) US8053438B2 (https=)
EP (1) EP2364308B1 (https=)
JP (1) JP5746972B2 (https=)
KR (1) KR20110083746A (https=)
CN (1) CN102300860B (https=)
AR (1) AR074358A1 (https=)
AU (1) AU2009313768B2 (https=)
BR (1) BRPI0922095A2 (https=)
CA (1) CA2742993C (https=)
CL (1) CL2011001094A1 (https=)
CO (1) CO6382157A2 (https=)
CR (1) CR20110326A (https=)
CY (1) CY1113680T1 (https=)
DK (1) DK2364308T3 (https=)
EA (1) EA019206B1 (https=)
ES (1) ES2397218T3 (https=)
HR (1) HRP20130054T1 (https=)
IL (1) IL212687A0 (https=)
MA (1) MA32889B1 (https=)
MX (1) MX2011005100A (https=)
NZ (1) NZ592508A (https=)
PE (1) PE20110581A1 (https=)
PL (1) PL2364308T3 (https=)
PT (1) PT2364308E (https=)
RS (1) RS52598B (https=)
SI (1) SI2364308T1 (https=)
SM (1) SMT201200061B (https=)
TN (1) TN2011000221A1 (https=)
TW (1) TWI396689B (https=)
WO (1) WO2010057121A1 (https=)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9156812B2 (en) 2008-06-04 2015-10-13 Bristol-Myers Squibb Company Crystalline form of 6-[(4S)-2-methyl-4-(2-naphthyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]pyridazin-3-amine
ES2397934T3 (es) * 2008-12-17 2013-03-12 Amgen Inc. Compuestos de aminopiridina y carboxipiridina como inhibidores de fosfodiesterasa 10
NZ594851A (en) 2009-02-05 2013-10-25 Takeda Pharmaceutical Pyridazinone compounds
US8815894B2 (en) 2009-05-12 2014-08-26 Bristol-Myers Squibb Company Crystalline forms of (S)-7-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydroisoquinoline and use thereof
AU2010247763B2 (en) * 2009-05-12 2015-12-24 Albany Molecular Research, Inc. 7-([1,2,4,]triazolo[1,5,-a]pyridin-6-yl)-4-(3,4-dichlorophenyl)-1,2,3,4- tetrahydroisoquinoline and use thereof
EA201201160A1 (ru) 2010-02-19 2013-04-30 Бёрингер Ингельхайм Интернациональ Гмбх Трициклические производные пиридина, лекарственные средства, содержащие такие соединения, их применение и способ их получения
US8846713B2 (en) 2010-06-24 2014-09-30 Takeda Pharmaceutical Company Limited Fused heterocyclic compounds as phosphodiesterases (PDEs) inhibitors
US8883788B2 (en) 2010-08-04 2014-11-11 Takeda Pharmaceutical Company Limited Fused heterocyclic ring compound
EP2601192B1 (en) 2010-08-04 2017-03-01 Takeda Pharmaceutical Company Limited Fused heterocyclic compounds
EP2604597B1 (en) 2010-08-10 2017-01-04 Takeda Pharmaceutical Company Limited Heterocyclic compound and use thereof inhibitor of phosphodiesterase 10a
KR20180099933A (ko) 2010-11-19 2018-09-05 리간드 파마슈티칼스 인코포레이티드 복소환 아민 및 이의 용도
CN107141309A (zh) 2011-01-11 2017-09-08 桑诺维恩药品公司 杂芳基化合物及其使用方法
JP5973990B2 (ja) * 2011-03-16 2016-08-23 武田薬品工業株式会社 縮合複素環化合物
TWI570122B (zh) 2011-06-22 2017-02-11 武田藥品工業股份有限公司 稠合雜環化合物之結晶
WO2014036528A2 (en) * 2012-08-31 2014-03-06 Ixchel Pharma, Llc Agents useful for treating obesity, diabetes and related disorders
CN102911135B (zh) * 2012-10-18 2016-01-13 内蒙古工业大学 2-巯基苯并噻唑类衍生物的合成方法
MX2015010041A (es) * 2013-02-05 2015-10-30 Purdue Pharma Lp Formulacion farmaceuticas resistentes a la alteracion.
US9464076B2 (en) 2013-03-15 2016-10-11 Daiichi Sankyo Company, Limited Benzothiophene derivative
WO2015006689A1 (en) 2013-07-12 2015-01-15 University Of South Alabama Treatment and diagnosis of cancer and precancerous conditions using pde10a inhibitors and methods to measure pde10a expression
BR112016006319A2 (pt) 2013-09-27 2017-08-01 Nimbus Iris Inc inibidores de irak e usos dos mesmos
US9657015B2 (en) 2014-07-31 2017-05-23 Boehringer Ingelheim International Gmbh Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity
CN104649882A (zh) * 2015-02-11 2015-05-27 南通恒盛精细化工有限公司 一种磷酸二酯酶抑制剂的中间体制备工艺
US10807983B2 (en) 2015-03-16 2020-10-20 Ligand Pharmaceuticals, Inc. Imidazo-fused heterocycles and uses thereof
SG11201801856XA (en) * 2015-09-18 2018-04-27 Kaken Pharmaceutical Co Ltd Biaryl derivative and medicine containing same
WO2019141259A1 (zh) * 2018-01-19 2019-07-25 苏州信诺维医药科技有限公司 杂环化合物、制备方法及其在医药上的应用
CN109020977B (zh) * 2018-10-26 2020-11-13 安庆奇创药业有限公司 一种Acalabrutinib的制备方法
CN116583577B (zh) 2020-12-17 2025-10-21 默克专利股份有限公司 杂芳族异硫氰酸酯
CN113929598A (zh) * 2021-11-24 2022-01-14 上海吉奉生物科技有限公司 一种(s)-2-叔丁氧羰基氨基-3-(4,4-二氟环己基)丙酸的合成方法
JP2025515208A (ja) * 2022-05-09 2025-05-13 ティーワイケー メディシンズ インコーポレーテッド 多環式化合物およびその使用
CN115894181A (zh) * 2022-09-30 2023-04-04 渭南高新区海泰新型电子材料有限责任公司 一种环己烯基环己基二氟苯类液晶化合物的合成方法

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4198417A (en) 1979-01-10 1980-04-15 American Hoechst Corporation Phenoxyphenylpiperidines
PT1635828E (pt) 2003-04-04 2008-07-01 Lundbeck & Co As H Derivados de 4-(2-feniloxifenil) piperidina ou de 1,2,3,6-tetrahidropiridina como inibidores da recaptação da serotonina
DE10337942A1 (de) 2003-08-18 2005-03-17 Merck Patent Gmbh Aminobenzimidazolderivate
DE10344223A1 (de) 2003-09-24 2005-04-21 Merck Patent Gmbh 1,3-Benzoxazolylderivate als Kinase-Inhibitoren
DE10349587A1 (de) 2003-10-24 2005-05-25 Merck Patent Gmbh Benzimidazolylderivate
US7470712B2 (en) 2004-01-21 2008-12-30 Bristol-Myers Squibb Company Amino-benzazoles as P2Y1 receptor inhibitors
ATE531705T1 (de) * 2004-05-18 2011-11-15 Schering Corp Substituierte 2-chinolyloxazole geeignet als pde4 inhibitoren
WO2005120514A1 (en) * 2004-06-07 2005-12-22 Pfizer Products Inc. Phosphodiesterase 10 inhibition as treatment for obesity-related and metabolic syndrome-related conditions
US20060183763A1 (en) * 2004-12-31 2006-08-17 Pfizer Inc Novel pyrrolidyl derivatives of heteroaromatic compounds
DE102005016634A1 (de) 2005-04-12 2006-10-19 Merck Patent Gmbh Neuartige Aza-Hetercyclen als Kinase-Inhibitoren
JP2009503073A (ja) 2005-08-02 2009-01-29 アイアールエム・リミテッド・ライアビリティ・カンパニー タンパク質キナーゼ阻害剤としての5−置換チアゾール−2−イルアミノ化合物および組成物
WO2007098169A1 (en) * 2006-02-21 2007-08-30 Amgen Inc. Cinnoline derivatives as phosphodiesterase 10 inhibitors
US7868177B2 (en) 2006-02-24 2011-01-11 Amgen Inc. Multi-cyclic compounds and method of use
JP2009535394A (ja) * 2006-05-02 2009-10-01 ファイザー・プロダクツ・インク Pde10阻害剤としての二環式ヘテロアリール化合物
US20080090834A1 (en) * 2006-07-06 2008-04-17 Pfizer Inc Selective azole pde10a inhibitor compounds
WO2008057280A1 (en) 2006-10-27 2008-05-15 Amgen Inc. Multi-cyclic compounds and methods of use
SI2125786T1 (sl) * 2006-12-21 2011-05-31 Pfizer Prod Inc Sukcinat sol 2-((4-(1-metil-4-(piridin-4-il)-1H-pirazol-3-il)fenoksi)metil)kinolina
ATE523508T1 (de) 2007-10-25 2011-09-15 Astrazeneca Ab Für die behandlung von zellproliferativen erkrankungen geeignete pyridin- und pyrazinderivate
WO2009081259A1 (en) 2007-12-21 2009-07-02 Pfizer Inc. Phenoxy-pyridyl derivatives
MX2010013876A (es) 2008-06-20 2011-03-04 Metabolex Inc Agonistas de arilo grpr119 y sus usos .

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CY1113680T1 (el) 2016-06-22
CO6382157A2 (es) 2012-02-15
TW201030006A (en) 2010-08-16
EA019206B1 (ru) 2014-01-30
CA2742993A1 (en) 2010-05-20
CN102300860B (zh) 2014-08-27
AU2009313768B2 (en) 2013-01-10
HRP20130054T1 (hr) 2013-02-28
SI2364308T1 (sl) 2013-01-31
BRPI0922095A2 (pt) 2019-09-24
EP2364308A1 (en) 2011-09-14
KR20110083746A (ko) 2011-07-20
US8053438B2 (en) 2011-11-08
US20110160202A1 (en) 2011-06-30
TWI396689B (zh) 2013-05-21
CN102300860A (zh) 2011-12-28
RS52598B (sr) 2013-04-30
ES2397218T3 (es) 2013-03-05
IL212687A0 (en) 2011-07-31
PT2364308E (pt) 2013-01-08
JP2012508776A (ja) 2012-04-12
US8247418B2 (en) 2012-08-21
SMT201200061B (it) 2013-01-14
EA201100748A1 (ru) 2011-10-31
PE20110581A1 (es) 2011-09-03
EP2364308B1 (en) 2012-10-24
US20100137278A1 (en) 2010-06-03
CA2742993C (en) 2015-01-20
AR074358A1 (es) 2011-01-12
PL2364308T3 (pl) 2013-03-29
TN2011000221A1 (en) 2012-12-17
MX2011005100A (es) 2011-05-30
WO2010057121A1 (en) 2010-05-20
US20110160182A1 (en) 2011-06-30
US20120277209A1 (en) 2012-11-01
MA32889B1 (fr) 2011-12-01
HK1161251A1 (en) 2012-08-24
DK2364308T3 (da) 2013-02-04
CR20110326A (es) 2011-07-28
US8329700B2 (en) 2012-12-11
NZ592508A (en) 2013-04-26
CL2011001094A1 (es) 2011-11-11
AU2009313768A1 (en) 2010-05-20

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