CA2847339C - Piperazine-substituted benzothiophene derivatives as antipsychotic agents - Google Patents

Piperazine-substituted benzothiophene derivatives as antipsychotic agents Download PDF

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Publication number
CA2847339C
CA2847339C CA2847339A CA2847339A CA2847339C CA 2847339 C CA2847339 C CA 2847339C CA 2847339 A CA2847339 A CA 2847339A CA 2847339 A CA2847339 A CA 2847339A CA 2847339 C CA2847339 C CA 2847339C
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group
alkyl group
thiophen
benzo
quinolin
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CA2847339A
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English (en)
French (fr)
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CA2847339A1 (en
Inventor
Hiroshi Yamashita
Yohji Sakurai
Motoyuki Miyamoto
Yuichi Nakamura
Hideaki Kuroda
Takuya MINOWA
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Otsuka Pharmaceutical Co Ltd
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Otsuka Pharmaceutical Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • A61K31/495—Heterocyclic 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
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • 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
    • A61K31/495—Heterocyclic 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
    • A61K31/50—Pyridazines; Hydrogenated pyridazines
    • A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
    • 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
    • A61K31/495—Heterocyclic 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
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
    • 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
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • 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
    • A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
    • A61K31/541—Non-condensed thiazines containing further heterocyclic rings
    • 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
    • A61K31/66—Phosphorus compounds
    • A61K31/675—Phosphorus compounds having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
    • 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
    • A61K31/695—Silicon compounds
    • 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
    • A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
    • 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
    • A61P25/04—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
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/06—Antimigraine agents
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • 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
    • A61P25/22—Anxiolytics
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Pain & Pain Management (AREA)
  • Psychiatry (AREA)
  • Hospice & Palliative Care (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Child & Adolescent Psychology (AREA)
  • Anesthesiology (AREA)
  • Otolaryngology (AREA)
  • Psychology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
CA2847339A 2011-09-08 2012-09-07 Piperazine-substituted benzothiophene derivatives as antipsychotic agents Active CA2847339C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201161532393P 2011-09-08 2011-09-08
US61/532,393 2011-09-08
PCT/JP2012/073556 WO2013035892A1 (en) 2011-09-08 2012-09-07 Piperazine- substituted benzothiophene derivatives as antipsychotic agents

Publications (2)

Publication Number Publication Date
CA2847339A1 CA2847339A1 (en) 2013-03-14
CA2847339C true CA2847339C (en) 2020-03-10

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
CA2847339A Active CA2847339C (en) 2011-09-08 2012-09-07 Piperazine-substituted benzothiophene derivatives as antipsychotic agents

Country Status (31)

Country Link
US (10) US9260420B2 (enExample)
EP (1) EP2753617B9 (enExample)
JP (1) JP6193848B2 (enExample)
KR (1) KR101998441B1 (enExample)
CN (1) CN103781783B (enExample)
AR (1) AR087809A1 (enExample)
AU (1) AU2012305212B2 (enExample)
BR (1) BR112014005235B1 (enExample)
CA (1) CA2847339C (enExample)
CO (1) CO6930362A2 (enExample)
CY (1) CY1118753T1 (enExample)
DK (1) DK2753617T3 (enExample)
EA (1) EA028160B1 (enExample)
ES (1) ES2572934T3 (enExample)
HR (1) HRP20160824T2 (enExample)
HU (1) HUE027746T2 (enExample)
IL (1) IL231116B (enExample)
JO (1) JO3227B1 (enExample)
MX (1) MX359515B (enExample)
MY (1) MY196864A (enExample)
PH (1) PH12014500496A1 (enExample)
PL (1) PL2753617T3 (enExample)
PT (1) PT2753617T (enExample)
RS (1) RS54894B9 (enExample)
SG (2) SG10201601731RA (enExample)
SI (1) SI2753617T1 (enExample)
SM (1) SMT201600205B (enExample)
TW (1) TWI568728B (enExample)
UA (1) UA112993C2 (enExample)
WO (1) WO2013035892A1 (enExample)
ZA (1) ZA201401433B (enExample)

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI320783B (en) * 2005-04-14 2010-02-21 Otsuka Pharma Co Ltd Heterocyclic compound
JO3227B1 (ar) * 2011-09-08 2018-03-08 Otsuka Pharma Co Ltd مشتقات بنزو ثيوفين بها استبدال ببرازين كعوامل مضادة للذهان
TW201332572A (zh) * 2011-12-28 2013-08-16 Otsuka Pharma Co Ltd 具有經取代的β-環糊精之藥物製劑
JOP20200109A1 (ar) 2012-04-23 2017-06-16 Otsuka Pharma Co Ltd مستحضر قابل للحقن
TWI562991B (en) * 2012-04-23 2016-12-21 Otsuka Pharma Co Ltd Dihydrate of benzothiophene compound or of a salt thereof, and process for producing the same
JP2014196292A (ja) * 2013-03-07 2014-10-16 大塚製薬株式会社 医薬
CN104447723A (zh) * 2014-11-28 2015-03-25 瑞阳制药有限公司 7-(4-(4-(苯并[b]噻吩基)-1-哌嗪基)丁氧基)-2(1H)-喹啉酮的制备方法
CN104829603A (zh) * 2015-05-19 2015-08-12 杭州新博思生物医药有限公司 A晶型依匹唑派盐酸盐及其制备方法
WO2017162536A1 (en) 2016-03-21 2017-09-28 H. Lundbeck A/S Vortioxetine prodrugs
PL233778B1 (pl) 2016-07-19 2019-11-29 Adamed Spolka Z Ograniczona Odpowiedzialnoscia Sposob wytwarzania brekspiprazolu oraz zastosowanie zwiazkow posrednich w sposobie wytwarzania brekspiprazolu
US10583840B2 (en) * 2016-09-08 2020-03-10 Ford Motor Company Methods and apparatus to monitor an activity level of a driver
CN106699745A (zh) * 2016-12-14 2017-05-24 上海博志研新药物技术有限公司 一种依匹哌唑甲醇合物、晶型a、及其制备方法和应用
US20180265472A1 (en) * 2017-03-17 2018-09-20 Scinopharm Taiwan, Ltd. Process for preparing aripiprazole lauroxil and intermediates thereof
CN107628999B (zh) * 2017-10-25 2019-07-02 苏州华健瑞达医药技术有限公司 阿立哌唑十二烷酸酯的制备方法
CN109988162A (zh) * 2017-12-29 2019-07-09 武汉兴华智慧医药科技有限公司 一种依匹哌唑衍生物及其制备方法
CN110218209B (zh) * 2018-03-02 2022-09-30 上海现代药物制剂工程研究中心有限公司 一种依匹哌唑月桂酸酯的晶型a、其制备方法及应用
CN108947990A (zh) * 2018-07-20 2018-12-07 成都苑东生物制药股份有限公司 一种苯并噻吩类化合物的制备方法
HUE065684T2 (hu) * 2019-01-11 2024-06-28 Alar Pharmaceuticals Inc Ketamin-pamoát és alkalmazása
TW202216676A (zh) * 2020-07-06 2022-05-01 美商塔朵根公司 用於心理疾病或心理強化的有益苯并噻吩組合物
US11229644B1 (en) * 2020-12-31 2022-01-25 Lake O'hara Llc Methods of treating psychiatric disorders in obese patients with brexpiprazole
WO2022176017A1 (ja) * 2021-02-16 2022-08-25 大塚製薬株式会社 非晶質体及び当該非晶質体を含む組成物
CN114044772A (zh) * 2021-11-29 2022-02-15 浙江国邦药业有限公司 一种依匹哌唑合成方法及其中间体
CN116407539B (zh) * 2021-12-30 2025-01-10 上海现代药物制剂工程研究中心有限公司 依匹哌唑甲基脂肪酸酯的用途
CN116410186B (zh) * 2021-12-30 2025-03-04 上海现代药物制剂工程研究中心有限公司 依匹哌唑甲基脂肪酸酯及其制备方法
WO2023186023A1 (zh) * 2022-03-30 2023-10-05 苏州旺山旺水生物医药股份有限公司 一类n-取代的喹啉酮化合物、其制备方法和用途
JP2023173950A (ja) * 2022-05-27 2023-12-07 同仁医薬化工株式会社 経口液剤
TW202438064A (zh) * 2023-02-27 2024-10-01 日商大塚製藥股份有限公司 用於治療心理疾病之經哌𠯤取代之苯并噻吩
AU2024266462A1 (en) * 2023-05-02 2025-08-28 Otsuka Pharmaceutical Co., Ltd. Heterocyclic compound and use thereof

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EA200500342A1 (ru) 2002-09-17 2005-08-25 УОРНЕР-ЛАМБЕРТ КОМПАНИ Эл-Эл-Си Гетероциклические замещённые пиперазины для лечения шизофрении
WO2004060374A1 (en) 2002-12-27 2004-07-22 Otsuka Pharmaceutical Co., Ltd. Carbostyril derivatives and serotonin reuptake inhibitors for treatment of mood disorders
US7160888B2 (en) 2003-08-22 2007-01-09 Warner Lambert Company Llc [1,8]naphthyridin-2-ones and related compounds for the treatment of schizophrenia
US20050254575A1 (en) 2004-05-12 2005-11-17 Nokia Corporation Multiple interoperability points for scalable media coding and transmission
DE102004031052A1 (de) 2004-06-25 2006-01-12 Bühler AG System und Verfahren zur Mahlgut-Charakterisierung in einem Walzenstuhl
US7802705B2 (en) 2004-07-29 2010-09-28 Magie Pression Co., Ltd. Method for forming pleat on fabric composed of polylactic acid yarn, and pleated fabric
JP4315393B2 (ja) * 2005-04-14 2009-08-19 大塚製薬株式会社 複素環化合物
TWI320783B (en) * 2005-04-14 2010-02-21 Otsuka Pharma Co Ltd Heterocyclic compound
WO2006111246A1 (de) 2005-04-18 2006-10-26 Loi Thermprocess Gmbh Industrieofen
JP4540700B2 (ja) * 2006-10-13 2010-09-08 大塚製薬株式会社 医薬
JP2011136906A (ja) 2008-04-18 2011-07-14 Otsuka Pharmaceut Co Ltd 複素環化合物
JP5732453B2 (ja) * 2009-06-25 2015-06-10 アルカーメス ファーマ アイルランド リミテッド Nh酸性化合物のプロドラッグ
PT2445502T (pt) 2009-06-25 2017-09-22 Alkermes Pharma Ireland Ltd Compostos heterocíclicos para o tratamento de distúrbios neurológicos e psicológicos
EP2521711B1 (en) 2010-01-07 2017-08-16 Alkermes Pharma Ireland Limited Quaternary ammonium salt prodrugs
NZ604423A (en) 2010-06-24 2015-01-30 Alkermes Pharma Ireland Ltd Prodrugs of nh-acidic compounds: ester, carbonate, carbamate and phosphonate derivatives
JP6013364B2 (ja) 2010-12-23 2016-10-25 アルカーメス ファーマ アイルランド リミテッド マルチプルapiローディングプロドラッグ
ES2972387T3 (es) 2011-03-18 2024-06-12 Alkermes Pharma Ireland Ltd Composiciones farmacéuticas que comprenden ésteres de sorbitán
JO3227B1 (ar) * 2011-09-08 2018-03-08 Otsuka Pharma Co Ltd مشتقات بنزو ثيوفين بها استبدال ببرازين كعوامل مضادة للذهان

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AU2012305212A1 (en) 2014-04-24
US20170071933A1 (en) 2017-03-16
EP2753617A1 (en) 2014-07-16
MY196864A (en) 2023-05-05
EA028160B1 (ru) 2017-10-31
PH12014500496A1 (en) 2014-04-14
SG10201601731RA (en) 2016-04-28
EP2753617B9 (en) 2017-01-25
US20180092907A1 (en) 2018-04-05
AR087809A1 (es) 2014-04-16
TWI568728B (zh) 2017-02-01
JP6193848B2 (ja) 2017-09-06
US20210052575A1 (en) 2021-02-25
ES2572934T9 (es) 2017-05-08
WO2013035892A1 (en) 2013-03-14
US20150045356A1 (en) 2015-02-12
IL231116A0 (en) 2014-04-30
CY1118753T1 (el) 2017-07-12
MX359515B (es) 2018-10-01
US20160143905A1 (en) 2016-05-26
RS54894B9 (sr) 2019-12-31
ES2572934T3 (es) 2016-06-03
US20180318294A1 (en) 2018-11-08
US20230099694A1 (en) 2023-03-30
US9260420B2 (en) 2016-02-16
AU2012305212B2 (en) 2016-12-08
NZ621837A (en) 2015-06-26
US20200061056A1 (en) 2020-02-27
US20190167672A1 (en) 2019-06-06
BR112014005235B1 (pt) 2022-03-29
JO3227B1 (ar) 2018-03-08
MX2014002254A (es) 2014-04-30
KR101998441B1 (ko) 2019-07-09
KR20140069109A (ko) 2014-06-09
PL2753617T3 (pl) 2016-10-31
ZA201401433B (en) 2015-05-27
SG11201400148QA (en) 2014-03-28
CN103781783A (zh) 2014-05-07
IL231116B (en) 2019-09-26
US9539252B2 (en) 2017-01-10
HK1195550A1 (zh) 2014-11-14
HUE027746T2 (en) 2016-10-28
RS54894B1 (sr) 2016-10-31
DK2753617T3 (en) 2016-07-25
JP2014526435A (ja) 2014-10-06
CO6930362A2 (es) 2014-04-28
HRP20160824T2 (hr) 2017-05-19
SMT201600205B (it) 2016-08-31
CN103781783B (zh) 2016-12-07
EA201490585A1 (ru) 2014-08-29
SI2753617T1 (sl) 2016-08-31
HRP20160824T1 (hr) 2016-08-26
BR112014005235A2 (pt) 2017-04-11
EP2753617B1 (en) 2016-04-13
US20260130904A1 (en) 2026-05-14
UA112993C2 (uk) 2016-11-25
PT2753617T (pt) 2016-07-13
TW201326160A (zh) 2013-07-01
CA2847339A1 (en) 2013-03-14

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