MX336477B - Derivado de aminoacido. - Google Patents

Derivado de aminoacido.

Info

Publication number
MX336477B
MX336477B MX2011002945A MX2011002945A MX336477B MX 336477 B MX336477 B MX 336477B MX 2011002945 A MX2011002945 A MX 2011002945A MX 2011002945 A MX2011002945 A MX 2011002945A MX 336477 B MX336477 B MX 336477B
Authority
MX
Mexico
Prior art keywords
amino acid
acid derivative
respect
analgesic activity
model animals
Prior art date
Application number
MX2011002945A
Other languages
English (en)
Other versions
MX2011002945A (es
Inventor
Tomohiro Ookubo
Ko Nakamura
Hiroyoshi Nanba
Hiroyuki Yoshida
Yoshitaka Nakazawa
Original Assignee
Nippon Zoki Pharmaceutical Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Nippon Zoki Pharmaceutical Co filed Critical Nippon Zoki Pharmaceutical Co
Publication of MX2011002945A publication Critical patent/MX2011002945A/es
Publication of MX336477B publication Critical patent/MX336477B/es

Links

Classifications

    • 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
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
    • A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P23/00—Anaesthetics
    • 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
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • 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
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/49—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/57—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
    • C07C279/14—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
    • C07C323/59—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton with acylated amino groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
    • C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
    • C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
    • C07D207/452—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide with hydrocarbon radicals, substituted by hetero atoms, directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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
    • C07D307/84—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D307/85—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
    • C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
    • C07D311/12—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 3 and unsubstituted in position 7
    • 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
    • C07D405/06—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 carbon chain containing only aliphatic carbon atoms
    • 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

Landscapes

  • 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)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Neurology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Epidemiology (AREA)
  • Neurosurgery (AREA)
  • Anesthesiology (AREA)
  • Indole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pyrane Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Furan Compounds (AREA)

Abstract

La presente invención se refiere a un derivado de aminoácido novedoso que tiene una excelente actividad analgésica. El derivado de aminoácido es un compuesto novedoso el cual exhibe una excelente actividad analgésica no únicamente con respecto a animales de un modelo de dolor nociceptivo, sino también con respecto a animales de un modelo de dolor neuropático y es extremadamente útil como agente médico para el tratamiento de varias condiciones dolorosas que exhiben un dolor agudo o crónico o un dolor neuropático.
MX2011002945A 2008-09-18 2009-09-17 Derivado de aminoacido. MX336477B (es)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2008239282 2008-09-18
PCT/JP2009/066217 WO2010032771A1 (ja) 2008-09-18 2009-09-17 アミノ酸誘導体

Publications (2)

Publication Number Publication Date
MX2011002945A MX2011002945A (es) 2011-06-16
MX336477B true MX336477B (es) 2016-01-21

Family

ID=42039593

Family Applications (1)

Application Number Title Priority Date Filing Date
MX2011002945A MX336477B (es) 2008-09-18 2009-09-17 Derivado de aminoacido.

Country Status (16)

Country Link
US (1) US9150510B2 (es)
EP (1) EP2345635B1 (es)
JP (1) JP5213961B2 (es)
KR (1) KR101375682B1 (es)
CN (1) CN102216260B (es)
AU (1) AU2009293750C1 (es)
BR (1) BRPI0919200A2 (es)
CA (1) CA2737431C (es)
HK (1) HK1159074A1 (es)
IL (1) IL211721A (es)
MX (1) MX336477B (es)
NZ (1) NZ591837A (es)
RU (1) RU2499790C2 (es)
TW (1) TWI447097B (es)
WO (1) WO2010032771A1 (es)
ZA (1) ZA201102450B (es)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5210405B2 (ja) * 2010-03-17 2013-06-12 日本臓器製薬株式会社 アミノ酸誘導体を含有する医薬及び該誘導体の製造方法
CN102126981A (zh) * 2010-12-02 2011-07-20 天津工业大学 一类含有l-氨基酸基团的手性单体
CN109526961B (zh) * 2018-11-28 2021-03-30 华南农业大学 苯丙烯酸化合物在预防和/或治疗植物病害中的应用
JP2023505233A (ja) * 2019-12-05 2023-02-08 フラッグシップ パイオニアリング イノベーションズ ブイ， インコーポレイテッド アシル化された活性薬剤並びに代謝異常及び非アルコール性脂肪性肝疾患の治療のためのそれらの使用の方法
US20210388142A1 (en) * 2020-06-16 2021-12-16 Johnson & Johnson Vision Care, Inc. Amino acid-based polymerizable compounds and ophthalmic devices prepared therefrom

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SU1066984A1 (ru) 1982-05-31 1984-01-15 Институт Биологической И Медицинской Химии Амн Ссср Способ получени @ -3-/2-фурил/-акрилоильных производных аминокислот или пептидов
JPH0784424B2 (ja) 1987-04-15 1995-09-13 味の素株式会社 チロシン誘導体及びその用途
EP0336356A3 (en) * 1988-04-05 1991-09-25 Abbott Laboratories Derivatives of tryptophan as cck antagonists
EP1490693A1 (en) * 2002-04-04 2004-12-29 Xzillion GmbH & CO.KG Method for characterising analytes
GB2389582A (en) * 2002-06-13 2003-12-17 Bayer Ag Pharmaceutically active carboxamides
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US20080262224A1 (en) * 2004-01-23 2008-10-23 Smithkline Beecham Corporation Method of Preparation of Benzofuran-2-Carboxylic Acid -Amide
KR20050078743A (ko) * 2004-02-02 2005-08-08 재단법인 목암생명공학연구소 로즈마린산의 하이드록실페닐 유도체를 유효성분으로 하는항암용 약학 조성물
US20080269282A1 (en) * 2004-08-02 2008-10-30 Genmedica Therapeutics Sl Compounds for Inhibiting Copper-Containing Amine Oxidases and Uses Thereof
AU2006259630B2 (en) * 2005-06-13 2011-10-27 Cleveland Biolabs, Inc. Methods of protecting against apoptosis using lipopeptides
US20070066646A1 (en) * 2005-08-02 2007-03-22 Genmedica Therapeutics Sl Compounds for Inhibiting Copper-Containing Amine Oxidases and Uses Thereof
EP1940785A2 (en) * 2005-09-08 2008-07-09 SmithKline Beecham Corporation Acyclic 1,4-diamines and uses thereof
JP5246833B2 (ja) 2005-12-16 2013-07-24 独立行政法人産業技術総合研究所 アディポネクチン産生増強剤
KR101378821B1 (ko) * 2006-01-24 2014-03-28 니폰 조키 세야쿠 가부시키가이샤 신규 히스티딘 유도체
DE102006033321A1 (de) 2006-07-17 2008-01-24 Westfälische Wilhelms-Universität Münster Medizinische Verwendung von N-Phenylpropenoyl-Aminosäurederivaten und verwandten Verbindungen
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WO2009039485A1 (en) * 2007-09-20 2009-03-26 University Of Utah Research Foundation Electrochemical deposition of polymers on metal substrates
JP5210405B2 (ja) * 2010-03-17 2013-06-12 日本臓器製薬株式会社 アミノ酸誘導体を含有する医薬及び該誘導体の製造方法

Also Published As

Publication number Publication date
CN102216260B (zh) 2015-07-15
IL211721A (en) 2015-07-30
JP5213961B2 (ja) 2013-06-19
EP2345635A4 (en) 2012-05-30
BRPI0919200A2 (pt) 2015-12-08
HK1159074A1 (en) 2012-07-27
TWI447097B (zh) 2014-08-01
KR20110061581A (ko) 2011-06-09
JPWO2010032771A1 (ja) 2012-02-09
ZA201102450B (en) 2011-12-28
EP2345635B1 (en) 2021-08-25
KR101375682B1 (ko) 2014-03-19
MX2011002945A (es) 2011-06-16
CN102216260A (zh) 2011-10-12
IL211721A0 (en) 2011-06-30
CA2737431C (en) 2016-03-29
RU2011114991A (ru) 2012-10-27
EP2345635A1 (en) 2011-07-20
TW201016645A (en) 2010-05-01
RU2499790C2 (ru) 2013-11-27
WO2010032771A1 (ja) 2010-03-25
AU2009293750B2 (en) 2014-05-22
US20110172442A1 (en) 2011-07-14
CA2737431A1 (en) 2010-03-25
NZ591837A (en) 2013-03-28
AU2009293750A1 (en) 2010-03-25
US9150510B2 (en) 2015-10-06
AU2009293750C1 (en) 2016-02-04

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