RU2480456C2 - Фенилпиразольные производные - Google Patents

Фенилпиразольные производные Download PDF

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Publication number
RU2480456C2
RU2480456C2 RU2010123924/04A RU2010123924A RU2480456C2 RU 2480456 C2 RU2480456 C2 RU 2480456C2 RU 2010123924/04 A RU2010123924/04 A RU 2010123924/04A RU 2010123924 A RU2010123924 A RU 2010123924A RU 2480456 C2 RU2480456 C2 RU 2480456C2
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RU
Russia
Prior art keywords
phenyl
alkyl
propoxy
methylpyrrolidin
halogen
Prior art date
Application number
RU2010123924/04A
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English (en)
Russian (ru)
Other versions
RU2010123924A (ru
Inventor
Тосио Накамура
Макото ТАЦУЗУКИ
Даи НОЗАВА
Томоко ТАМИТА
Сейдзи МАСУДА
Хироси ОХТА
Сухеи КАСИВА
Ая ФУДЗИНО
Сигеюки ТАКИ
Тосихару СИМАЗАКИ
Original Assignee
Тайсо Фармасьютикал Ко., Лтд.
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Application filed by Тайсо Фармасьютикал Ко., Лтд. filed Critical Тайсо Фармасьютикал Ко., Лтд.
Publication of RU2010123924A publication Critical patent/RU2010123924A/ru
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Publication of RU2480456C2 publication Critical patent/RU2480456C2/ru

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/02—Nasal agents, e.g. decongestants
    • 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
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/08—Antiepileptics; Anticonvulsants
    • 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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • 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
    • A61P25/20—Hypnotics; Sedatives
    • 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
    • A61P25/24—Antidepressants
    • 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
    • A61P25/28—Drugs 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • 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
    • A61P37/08—Antiallergic 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
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D231/38—Nitrogen atoms
    • C07D231/40—Acylated on said nitrogen atom
    • 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
    • C07D401/14—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 three or more hetero rings
    • 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
    • C07D403/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • 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
    • C07D403/12—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 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
    • C07D413/02—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
    • C07D413/04—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 directly linked by a ring-member-to-ring-member bond
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Diabetes (AREA)
  • Psychiatry (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Pulmonology (AREA)
  • Pain & Pain Management (AREA)
  • Endocrinology (AREA)
  • Emergency Medicine (AREA)
  • Child & Adolescent Psychology (AREA)
  • Hospice & Palliative Care (AREA)
  • Immunology (AREA)
  • Anesthesiology (AREA)
  • Otolaryngology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
RU2010123924/04A 2007-11-13 2008-11-13 Фенилпиразольные производные RU2480456C2 (ru)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
JP2007-294040 2007-11-13
JP2007294040 2007-11-13
JP2008153736 2008-06-12
JP2008-153736 2008-06-12
PCT/JP2008/070712 WO2009063953A1 (ja) 2007-11-13 2008-11-13 フェニルピラゾール誘導体

Publications (2)

Publication Number Publication Date
RU2010123924A RU2010123924A (ru) 2011-12-20
RU2480456C2 true RU2480456C2 (ru) 2013-04-27

Family

ID=40638800

Family Applications (1)

Application Number Title Priority Date Filing Date
RU2010123924/04A RU2480456C2 (ru) 2007-11-13 2008-11-13 Фенилпиразольные производные

Country Status (24)

Country Link
US (3) US7888354B2 (enExample)
EP (1) EP2221298B1 (enExample)
JP (2) JP4543344B2 (enExample)
KR (1) KR101571176B1 (enExample)
CN (1) CN101855211B (enExample)
AU (1) AU2008321823B2 (enExample)
BR (1) BRPI0820432B8 (enExample)
CA (1) CA2705502C (enExample)
CY (1) CY1114877T1 (enExample)
DK (1) DK2221298T3 (enExample)
ES (1) ES2436146T3 (enExample)
HR (1) HRP20131060T1 (enExample)
IL (2) IL205509A (enExample)
MX (1) MX2010005225A (enExample)
MY (1) MY173546A (enExample)
NZ (1) NZ585661A (enExample)
PH (1) PH12012501917A1 (enExample)
PL (1) PL2221298T3 (enExample)
PT (1) PT2221298E (enExample)
RS (1) RS53125B (enExample)
RU (1) RU2480456C2 (enExample)
SI (1) SI2221298T1 (enExample)
WO (1) WO2009063953A1 (enExample)
ZA (1) ZA201003111B (enExample)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2618228C2 (ru) * 2011-12-08 2017-05-03 Тайсо Фармасьютикал Ко., Лтд. Производное фенилпиррола
RU2666730C2 (ru) * 2012-12-07 2018-09-12 Кемосентрикс, Инк. Диазольные лактамы

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100113776A1 (en) * 2006-12-14 2010-05-06 Taisho Pharmaceutical Co.,Ltd. Pyrazole derivative
CN101855211B (zh) * 2007-11-13 2013-06-12 大正制药株式会社 苯基吡唑衍生物
JP5740838B2 (ja) * 2009-05-12 2015-07-01 大正製薬株式会社 フェニルピラゾール誘導体
WO2013100054A1 (ja) 2011-12-27 2013-07-04 大正製薬株式会社 フェニルトリアゾール誘導体
WO2013151982A1 (en) 2012-04-03 2013-10-10 Arena Pharmaceuticals, Inc. Methods and compounds useful in treating pruritus, and methods for identifying such compounds
WO2014111356A1 (en) * 2013-01-17 2014-07-24 F. Hoffmann-La Roche Ag Oxytocin receptor agonists for the treatment of cns diseases
IL261998B2 (en) 2016-04-07 2023-03-01 Chemocentryx Inc Reducing your burden by giving ccr1 antagonists in combination with pd-1 inhibitors or pd-l1 inhibitors

Citations (1)

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RU2128172C1 (ru) * 1992-02-05 1999-03-27 Фудзисава Фармасьютикал Ко., Лтд. Производные пиразола или их фармацевтически приемлемые соли

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CZ2003686A3 (cs) 2000-08-08 2003-08-13 Ortho Mcneil Pharmaceutical, Inc. Neimidazolové aryloxypiperidiny
US6316475B1 (en) 2000-11-17 2001-11-13 Abbott Laboratories Aminoalkoxybiphenylcarboxamides as histamine-3 receptor ligands and their therapeutic applications
JP4612990B2 (ja) * 2001-03-16 2011-01-12 アボット・ラボラトリーズ ヒスタミン−３受容体リガンドとしての新規アミンおよびそれらの治療的適用
US7595316B2 (en) 2003-06-27 2009-09-29 Banyu Pharmaceutical Co., Ltd. Heteroaryloxy nitrogenous saturated heterocyclic derivative
JP2007531753A (ja) 2004-03-31 2007-11-08 ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ 非イミダゾール系複素環式化合物
GB0408083D0 (en) 2004-04-08 2004-05-12 Glaxo Group Ltd Novel compounds
FR2870846B1 (fr) 2004-05-25 2006-08-04 Sanofi Synthelabo Derives de tetrahydroisoquinolylsulfonamides, leur preparation et leur utilisation en therapeutique
SE0401971D0 (sv) 2004-08-02 2004-08-02 Astrazeneca Ab Piperidne derivatives
EP1784400B1 (en) 2004-08-23 2015-01-14 Eli Lilly And Company Histamine h3 receptor agents, preparation and therapeutic uses
BRPI0518222A (pt) 2004-10-19 2008-11-04 Hoffmann La Roche composto, processo para a sua manufatura, composições farmacêuticas que os compreendem, método para o tratamento e/ou prevenção de enfermidades que estão associadas com a modulação de receptores de h3 e utilização dos mesmos
WO2006046131A1 (en) 2004-10-29 2006-05-04 Pfizer Products Inc. Tetralin histamine-3 receptor antagonists
WO2006059778A1 (ja) 2004-12-01 2006-06-08 Banyu Pharmaceutical Co., Ltd. 置換ピリドン誘導体
BRPI0518841A2 (pt) 2004-12-07 2008-12-09 Glaxo Group Ltd derivados de indenila e uso destes para o tratamento de transtornos neurolàgicos
CA2602336A1 (en) * 2005-03-31 2006-10-05 Ucb Pharma S.A. Compounds comprising an oxazole or thiazole moiety, processes for making them, and their uses
CN101151244B (zh) 2005-04-01 2014-09-03 伊莱利利公司 组胺h3受体活性剂、制备和治疗用途
DE102005033448A1 (de) * 2005-07-18 2007-01-25 Josef Gail Druckgas-Zylinderläufermotor
GB0514811D0 (en) * 2005-07-19 2005-08-24 Glaxo Group Ltd Compounds
GB0514812D0 (en) 2005-07-19 2005-08-24 Glaxo Group Ltd Compounds
DK1988777T3 (da) * 2006-02-09 2012-01-16 Athersys Inc Pyrazoler til behandling af fedme og andre cns-lidelser
US20100113776A1 (en) 2006-12-14 2010-05-06 Taisho Pharmaceutical Co.,Ltd. Pyrazole derivative
EP2134673A1 (en) * 2007-04-12 2009-12-23 DSM Fine Chemicals Austria Nfg GmbH & Co KG Improved process for preparing o-chloromethylphenylglyoxylic esters, improved process for preparing (e)-2-(2-chloromethylphenyl)-2-alkoximinoacetic esters, and novel intermediates for their preparation
CN101855211B (zh) * 2007-11-13 2013-06-12 大正制药株式会社 苯基吡唑衍生物

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2128172C1 (ru) * 1992-02-05 1999-03-27 Фудзисава Фармасьютикал Ко., Лтд. Производные пиразола или их фармацевтически приемлемые соли

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2618228C2 (ru) * 2011-12-08 2017-05-03 Тайсо Фармасьютикал Ко., Лтд. Производное фенилпиррола
RU2666730C2 (ru) * 2012-12-07 2018-09-12 Кемосентрикс, Инк. Диазольные лактамы

Also Published As

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US20100267687A1 (en) 2010-10-21
PH12012501917A1 (en) 2014-10-17
PL2221298T3 (pl) 2014-05-30
SI2221298T1 (sl) 2013-12-31
IL205509A0 (en) 2010-12-30
US8183387B2 (en) 2012-05-22
CN101855211B (zh) 2013-06-12
MY173546A (en) 2020-02-04
MX2010005225A (es) 2010-05-27
AU2008321823B2 (en) 2013-03-07
JPWO2009063953A1 (ja) 2011-03-31
EP2221298A4 (en) 2011-09-21
US20110065668A1 (en) 2011-03-17
EP2221298A1 (en) 2010-08-25
DK2221298T3 (da) 2013-11-18
CA2705502C (en) 2016-01-26
IL236083A0 (en) 2015-01-29
RS53125B (sr) 2014-06-30
AU2008321823A1 (en) 2009-05-22
BRPI0820432A2 (pt) 2015-05-26
PT2221298E (pt) 2013-12-03
JP5375639B2 (ja) 2013-12-25
ZA201003111B (en) 2011-08-31
IL205509A (en) 2015-09-24
US7888354B2 (en) 2011-02-15
RU2010123924A (ru) 2011-12-20
WO2009063953A1 (ja) 2009-05-22
EP2221298B1 (en) 2013-11-06
HK1145834A1 (en) 2011-05-06
CA2705502A1 (en) 2009-05-22
IL236083A (en) 2016-12-29
JP4543344B2 (ja) 2010-09-15
CN101855211A (zh) 2010-10-06
ES2436146T3 (es) 2013-12-27
NZ585661A (en) 2012-04-27
US20110065667A1 (en) 2011-03-17
US8193176B2 (en) 2012-06-05
JP2010143943A (ja) 2010-07-01
BRPI0820432B1 (pt) 2020-01-14
CY1114877T1 (el) 2016-12-14
KR101571176B1 (ko) 2015-11-23
HRP20131060T1 (hr) 2013-12-20
KR20100083795A (ko) 2010-07-22
BRPI0820432B8 (pt) 2021-05-25

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