TWI453197B - 可用作抗菌劑之氟吡啶酮衍生物 - Google Patents

可用作抗菌劑之氟吡啶酮衍生物 Download PDF

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Publication number
TWI453197B
TWI453197B TW101107363A TW101107363A TWI453197B TW I453197 B TWI453197 B TW I453197B TW 101107363 A TW101107363 A TW 101107363A TW 101107363 A TW101107363 A TW 101107363A TW I453197 B TWI453197 B TW I453197B
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TW
Taiwan
Prior art keywords
fluoro
methyl
methylsulfonyl
butanamine
mmol
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TW101107363A
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English (en)
Chinese (zh)
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TW201249798A (en
Inventor
Matthew Frank Brown
Ye Che
Michael Joseph Melnick
Justin Montgomery
Mark Stephen Plummer
Loren Price
Usa Reilly
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Pfizer
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Publication of TW201249798A publication Critical patent/TW201249798A/zh
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • 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
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/69—Two or more oxygen atoms
    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D401/10—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 carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
TW101107363A 2011-03-07 2012-03-05 可用作抗菌劑之氟吡啶酮衍生物 TWI453197B (zh)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US201161449825P 2011-03-07 2011-03-07

Publications (2)

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TW201249798A TW201249798A (en) 2012-12-16
TWI453197B true TWI453197B (zh) 2014-09-21

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US (2) US8624034B2 (enExample)
EP (1) EP2683689B1 (enExample)
JP (1) JP5620020B2 (enExample)
KR (1) KR101593288B1 (enExample)
CN (2) CN103443079B (enExample)
AP (1) AP3336A (enExample)
AR (1) AR085615A1 (enExample)
AU (1) AU2012226473B8 (enExample)
BR (1) BR112013022536B1 (enExample)
CA (1) CA2828337C (enExample)
CL (1) CL2013002417A1 (enExample)
CO (1) CO6761338A2 (enExample)
CR (1) CR20130403A (enExample)
CU (1) CU20130117A7 (enExample)
DO (1) DOP2013000200A (enExample)
EA (1) EA024782B1 (enExample)
EC (1) ECSP13012928A (enExample)
ES (1) ES2626457T3 (enExample)
GE (1) GEP20156370B (enExample)
GT (1) GT201300213A (enExample)
HK (1) HK1209734A1 (enExample)
IL (1) IL228100A0 (enExample)
MA (1) MA34963B1 (enExample)
MX (1) MX341977B (enExample)
NI (1) NI201300077A (enExample)
PE (1) PE20140397A1 (enExample)
PH (1) PH12013501780A1 (enExample)
SG (1) SG192766A1 (enExample)
TN (1) TN2013000353A1 (enExample)
TW (1) TWI453197B (enExample)
UA (1) UA107423C2 (enExample)
UY (1) UY33936A (enExample)
WO (1) WO2012120397A1 (enExample)
ZA (1) ZA201306515B (enExample)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8722686B2 (en) 2008-09-19 2014-05-13 Pfizer Inc. Hydroxamic acid derivatives useful as antibacterial agents
PL2512474T3 (pl) 2009-12-16 2015-03-31 Pfizer N-przyłączone pochodne kwasu hydroksamowego użyteczne jako środki przeciwbakteryjne
GEP20156370B (en) 2011-03-07 2015-09-25 Pfizer Fluoro-pyridinone derivatives useful as antibacterial agents
EP2694488B1 (en) 2011-04-08 2014-11-12 Pfizer Inc Isoxazole derivatives useful as antibacterial agents
EP2694481B1 (en) * 2011-04-08 2015-12-30 Pfizer Inc Imidazole, pyrazole, and triazole derivatives useful as antibacterial agents
AR097617A1 (es) 2013-09-13 2016-04-06 Actelion Pharmaceuticals Ltd Derivados antibacterianos del 2h-indazol
WO2015085238A1 (en) * 2013-12-05 2015-06-11 The Regents Of The University Of California, A California Corporation Inhibitors of lpxc
JP6407288B2 (ja) 2013-12-19 2018-10-17 イドーシア ファーマシューティカルズ リミテッドＩｄｏｒｓｉａ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｌｔｄ 抗菌性１ｈ−インダゾール及び１ｈ−インドール誘導体
AR099612A1 (es) 2014-03-04 2016-08-03 Actelion Pharmaceuticals Ltd Derivados antibacterianos de 1,2-dihidro-3h-pirrolo[1,2-c]imidazol-3-ona
EP3134401B1 (en) 2014-04-22 2018-06-13 Novartis AG Isoxazoline hydroxamic acid derivatives as lpxc inhibitors
EP3143007B1 (en) 2014-05-16 2018-07-11 Idorsia Pharmaceuticals Ltd Antibacterial quinazoline-4(3h)-one derivatives
JP6195684B2 (ja) 2014-06-03 2017-09-13 アクテリオン ファーマシューティカルズ リミテッドＡｃｔｅｌｉｏｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｌｔｄ ピラゾール化合物及びｔ型カルシウムチャンネルブロッカーとしてのそれらの使用
WO2016079688A1 (en) 2014-11-19 2016-05-26 Actelion Pharmaceuticals Ltd Antibacterial benzothiazole derivatives
CU24443B1 (es) 2014-12-16 2019-10-04 Novartis Ag COMPUESTOS DE ISOXAZOL DE ÁCIDO HIDROXÁMICO COMO INHIBIDORES DE LpxC
CN104876883B (zh) * 2015-06-05 2017-11-28 安徽联创生物医药股份有限公司 抗失眠药物苏沃雷生中间体的合成方法
AR105646A1 (es) * 2015-08-11 2017-10-25 Actelion Pharmaceuticals Ltd Agentes antibacterianos de 1,2-dihidro-3h-pirrolo[1,2-c]imidazol-3-ona sustituida
AR105889A1 (es) 2015-09-03 2017-11-22 Actelion Pharmaceuticals Ltd Compuestos antibacterianos 1,2-dihidro-3h-pirrolo[1,2-c]imidazol-3-ona sustituidos
HRP20201524T1 (hr) 2016-06-14 2021-03-05 Novartis Ag Kristalni oblik (r)-4-(5-(ciklopropiletinil) izoksazol-3 -il)-n-hidroksi-2-metil-2-(metilsufonil) butanamid kao antibakterijsko sredstvo
LT3554490T (lt) 2016-12-16 2022-04-25 Idorsia Pharmaceuticals Ltd Farmacinis derinys, apimantis t tipo kalcio kanalo blokatorių
CA3050348A1 (en) 2017-02-06 2018-08-09 Idorsia Pharmaceuticals Ltd A novel process for the synthesis of 1-aryl-1-trifluoromethylcyclopropanes
MX2020009584A (es) * 2018-03-15 2020-10-05 Pfizer Fosfatos y boronatos de piridinona y pirimidinona utiles como agentes antibacterianos.
US11981696B2 (en) 2018-03-15 2024-05-14 Pfizer Inc. Fluoro-pyridinone phosphates and boronates useful as antibacterial agents
CN110699312B (zh) * 2019-11-28 2022-08-12 西北农林科技大学 一种猪种布鲁氏菌bi-1基因缺失菌株及其构建方法和应用

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100022605A1 (en) * 2005-12-15 2010-01-28 Vicuron Pharmaceuticals Inc. N-hydroxyamide derivatives possessing antibacterial activity
WO2010017060A1 (en) * 2008-08-04 2010-02-11 Schering Corporation Urea derivatives as antibacterial agents
WO2011073845A1 (en) * 2009-12-16 2011-06-23 Pfizer Inc. N-linked hydroxamic acid derivatives useful as antibacterial agents

Family Cites Families (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4769461A (en) 1986-09-16 1988-09-06 American Home Products Corporation Quinolinyl benzene hydroxamic acids as anti-inflammatory/antiallergic agents
US5110831A (en) 1990-11-30 1992-05-05 Du Pont Merck Pharmaceutical Company Vinylogous hydroxamic acids and derivatives thereof as 5-lipoxygenase inhibitors
CN1298299A (zh) 1998-02-07 2001-06-06 英国生物技术药物有限公司 抗菌剂
GB9925470D0 (en) 1999-10-27 1999-12-29 Smithkline Beecham Plc Novel compounds
JPWO2002074298A1 (ja) 2001-03-21 2004-07-08 小野薬品工業株式会社 Ｉｌ−６産生阻害剤
ES2180456B1 (es) 2001-07-20 2004-05-01 Laboratorios S.A.L.V.A.T., S.A. Isoxazoles sustituidos y su utilizacion como antibioticos.
ES2334990T3 (es) * 2002-02-14 2010-03-18 Pharmacia Corporation Piridinonas sustituidas como moduladores de p38 map quinasa.
SG159388A1 (en) 2003-01-08 2010-03-30 Chiron Corp Antibacterial agents
GB0302431D0 (en) 2003-01-30 2003-03-05 Glaxo Group Ltd Novel compounds
WO2006063281A2 (en) 2004-12-10 2006-06-15 Emory University 2' and 3' - substituted cyclobutyl nucleoside analogs for the treatment of viral infections and abnormal cellular proliferation
WO2006118155A1 (ja) 2005-04-27 2006-11-09 Ishihara Sangyo Kaisha, Ltd. ビフェニル誘導体又はその塩、並びにそれらを有効成分として含有する農園芸用殺菌剤
WO2006124897A2 (en) 2005-05-13 2006-11-23 Lexicon Genetics Incorporated Methods and compositions for improving cognition
WO2008045671A1 (en) 2006-10-06 2008-04-17 Janssen Pharmaceutica, N.V. Matrix metalloprotease inhibitors
US7879911B2 (en) 2007-02-01 2011-02-01 Johnson Alan T Hydroxamic acid derivatives of phenoxy-acetic acids and analogs useful as therapeutic agents for treating anthrax poisoning
JP5227304B2 (ja) 2007-02-28 2013-07-03 大正製薬株式会社 新規なヒドロキサム酸誘導体
WO2008115262A2 (en) 2007-03-20 2008-09-25 Curis, Inc. Hsp90 inhibitors containing a zinc binding moiety
CN101239978A (zh) * 2008-03-05 2008-08-13 南方医科大学 一种咪唑并吡啶类化合物
JP5455913B2 (ja) 2008-08-27 2014-03-26 大正製薬株式会社 ナフチリジン−ｎ−オキシドを有する新規ヒドロキサム酸誘導体
US8372885B2 (en) 2008-09-17 2013-02-12 Novartis Ag Organic compounds and their uses
US8722686B2 (en) 2008-09-19 2014-05-13 Pfizer Inc. Hydroxamic acid derivatives useful as antibacterial agents
WO2010100475A1 (en) 2009-03-02 2010-09-10 Astrazeneca Ab Hydroxamic acid derivatives as gram-negative antibacterial agents
WO2010147975A1 (en) * 2009-06-16 2010-12-23 Schering Corporation Gamma secretase modulators
WO2010147969A2 (en) * 2009-06-16 2010-12-23 Schering Corporation Gamma secretase modulators
GEP20156370B (en) 2011-03-07 2015-09-25 Pfizer Fluoro-pyridinone derivatives useful as antibacterial agents
EP2694488B1 (en) 2011-04-08 2014-11-12 Pfizer Inc Isoxazole derivatives useful as antibacterial agents
EP2694481B1 (en) 2011-04-08 2015-12-30 Pfizer Inc Imidazole, pyrazole, and triazole derivatives useful as antibacterial agents

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100022605A1 (en) * 2005-12-15 2010-01-28 Vicuron Pharmaceuticals Inc. N-hydroxyamide derivatives possessing antibacterial activity
WO2010017060A1 (en) * 2008-08-04 2010-02-11 Schering Corporation Urea derivatives as antibacterial agents
WO2011073845A1 (en) * 2009-12-16 2011-06-23 Pfizer Inc. N-linked hydroxamic acid derivatives useful as antibacterial agents

Also Published As

Publication number Publication date
AU2012226473B8 (en) 2015-10-15
WO2012120397A1 (en) 2012-09-13
AR085615A1 (es) 2013-10-16
PH12013501780A1 (en) 2019-07-03
UY33936A (es) 2012-10-31
MX341977B (es) 2016-09-07
CL2013002417A1 (es) 2013-12-13
KR20130131459A (ko) 2013-12-03
AU2012226473B2 (en) 2015-06-11
US20140057919A1 (en) 2014-02-27
HK1191951A1 (en) 2014-08-08
SG192766A1 (en) 2013-09-30
AU2012226473A1 (en) 2013-09-05
EA024782B1 (ru) 2016-10-31
TN2013000353A1 (fr) 2015-01-20
MX2013010276A (es) 2013-10-01
US20120232083A1 (en) 2012-09-13
IL228100A0 (en) 2013-09-30
GT201300213A (es) 2014-06-06
CN104529883A (zh) 2015-04-22
CR20130403A (es) 2013-09-18
CA2828337A1 (en) 2012-09-13
NI201300077A (es) 2014-01-07
EA201391072A1 (ru) 2014-02-28
HK1209734A1 (en) 2016-04-08
TW201249798A (en) 2012-12-16
CN103443079A (zh) 2013-12-11
CU20130117A7 (es) 2013-10-29
CO6761338A2 (es) 2013-09-30
JP5620020B2 (ja) 2014-11-05
ES2626457T3 (es) 2017-07-25
CN103443079B (zh) 2015-06-03
EP2683689A1 (en) 2014-01-15
MA34963B1 (fr) 2014-03-01
NZ614205A (en) 2014-06-27
EP2683689B1 (en) 2017-04-12
KR101593288B1 (ko) 2016-02-11
US8779148B2 (en) 2014-07-15
UA107423C2 (en) 2014-12-25
ECSP13012928A (es) 2013-11-29
AP2013007074A0 (en) 2013-08-31
PE20140397A1 (es) 2014-03-28
BR112013022536A2 (pt) 2016-11-29
DOP2013000200A (es) 2014-06-15
US8624034B2 (en) 2014-01-07
CA2828337C (en) 2016-05-03
AP3336A (en) 2015-07-31
ZA201306515B (en) 2014-05-28
GEP20156370B (en) 2015-09-25
BR112013022536B1 (pt) 2020-05-26
JP2014507464A (ja) 2014-03-27

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