EA028818B1 - Производные амидов в качестве антагонистов рецептора к лизофосфатидной кислоте - Google Patents

Производные амидов в качестве антагонистов рецептора к лизофосфатидной кислоте Download PDF

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Publication number
EA028818B1
EA028818B1 EA201690390A EA201690390A EA028818B1 EA 028818 B1 EA028818 B1 EA 028818B1 EA 201690390 A EA201690390 A EA 201690390A EA 201690390 A EA201690390 A EA 201690390A EA 028818 B1 EA028818 B1 EA 028818B1
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EA
Eurasian Patent Office
Prior art keywords
methyl
benzoic acid
benzamido
fluorophenoxy
methoxyphenoxy
Prior art date
Application number
EA201690390A
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English (en)
Russian (ru)
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EA201690390A1 (ru
Inventor
Уильям Баффхэм
Ханна Кэннинг
Ричард Дейвенпорт
Уильям Фарнаби
Стивен Мэк
Алка Пармар
Сьюзанн Райт
Original Assignee
Такеда Фармасьютикал Компани Лимитед
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Publication of EA201690390A1 publication Critical patent/EA201690390A1/ru
Publication of EA028818B1 publication Critical patent/EA028818B1/ru

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • 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
    • 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
    • A61K31/275—Nitriles; Isonitriles
    • A61K31/277—Nitriles; Isonitriles having a ring, e.g. verapamil
    • 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
    • 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
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • 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
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • 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
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/46—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring 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
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/52—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • 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
    • C07C255/54—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and etherified hydroxy groups bound to the carbon skeleton
    • 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/04—Systems containing only non-condensed rings with a four-membered ring

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pain & Pain Management (AREA)
  • Vascular Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Cardiology (AREA)
  • Rheumatology (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Peptides Or Proteins (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EA201690390A 2013-08-20 2014-08-20 Производные амидов в качестве антагонистов рецептора к лизофосфатидной кислоте EA028818B1 (ru)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB1314926.5A GB201314926D0 (en) 2013-08-20 2013-08-20 Novel Compounds
PCT/GB2014/052558 WO2015025164A1 (en) 2013-08-20 2014-08-20 Amide derivatives as lysophosphatidic acid receptor antagonists

Publications (2)

Publication Number Publication Date
EA201690390A1 EA201690390A1 (ru) 2016-08-31
EA028818B1 true EA028818B1 (ru) 2018-01-31

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EA201690390A EA028818B1 (ru) 2013-08-20 2014-08-20 Производные амидов в качестве антагонистов рецептора к лизофосфатидной кислоте

Country Status (24)

Country Link
US (3) US9464060B2 (enExample)
EP (1) EP3036215A1 (enExample)
JP (1) JP6422974B2 (enExample)
KR (1) KR20160045797A (enExample)
CN (1) CN105473548B (enExample)
AR (1) AR097403A1 (enExample)
AU (1) AU2014310404B2 (enExample)
CA (1) CA2921742A1 (enExample)
CL (1) CL2016000387A1 (enExample)
CR (1) CR20160084A (enExample)
EA (1) EA028818B1 (enExample)
GB (1) GB201314926D0 (enExample)
HK (1) HK1225712A1 (enExample)
IL (1) IL243780A0 (enExample)
MA (1) MA38854B1 (enExample)
MX (1) MX2016001896A (enExample)
PE (1) PE20160284A1 (enExample)
PH (1) PH12016500322A1 (enExample)
SG (1) SG11201601250TA (enExample)
TN (1) TN2016000061A1 (enExample)
TW (1) TW201536722A (enExample)
UY (1) UY35708A (enExample)
WO (1) WO2015025164A1 (enExample)
ZA (1) ZA201600753B (enExample)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB201314926D0 (en) 2013-08-20 2013-10-02 Takeda Pharmaceutical Novel Compounds
EP3870292A4 (en) 2018-10-26 2022-11-09 The Research Foundation for The State University of New York COMBINATION OF SEROTONIN-SPECIFIC RESUPPUT INHIBITOR AND SEROTONIN 1A RECEPTOR PARTIAL AGONIST TO REDUCE L-DOPA-INDUCED DYSKINESIA
MX2022001264A (es) 2019-07-30 2022-02-22 Taisho Pharmaceutical Co Ltd Compuesto de urea para antagonizar el receptor del acido lisofosfatidico tipo 1.
JP7431961B2 (ja) 2019-11-15 2024-02-15 ギリアード サイエンシーズ， インコーポレイテッド Ｌｐａ受容体アンタゴニストとしてのトリアゾールカルバメートピリジルスルホンアミド及びその使用
TWI838626B (zh) 2020-06-03 2024-04-11 美商基利科學股份有限公司 Lpa受體拮抗劑及其用途
CA3185689A1 (en) 2020-06-03 2021-12-09 Gilead Sciences, Inc. Lpa receptor antagonists and uses thereof
CN117295717A (zh) 2021-05-11 2023-12-26 吉利德科学公司 Lpa受体拮抗剂及其用途
JP7709612B2 (ja) 2021-12-08 2025-07-16 ギリアード サイエンシーズ， インコーポレイテッド Ｌｐａ受容体アンタゴニスト及びそれらの使用
WO2024252334A1 (en) * 2023-06-06 2024-12-12 Gpcr Therapeutics, Inc. Gpcr inhibitors and uses thereof

Citations (1)

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Publication number Priority date Publication date Assignee Title
EP1550461A1 (en) * 2002-06-26 2005-07-06 Ono Pharmaceutical Co., Ltd. Remedy for chronic disease

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FR2707641B1 (fr) * 1993-07-16 1995-08-25 Fournier Ind & Sante Composés de l'imidazol-5-carboxamide, leur procédé de préparation leurs intermédiaires et leur utilisation en thérapeutique.
ATE293109T1 (de) 2001-01-31 2005-04-15 Pfizer Prod Inc Nikotinsäureamid-derivate und ihre mimetika als inhibitoren von pde4-isozyms
DE10110749A1 (de) 2001-03-07 2002-09-12 Bayer Ag Substituierte Aminodicarbonsäurederivate
TW200408393A (en) * 2002-10-03 2004-06-01 Ono Pharmaceutical Co Antagonist of lysophosphatidine acid receptor
JP2013501064A (ja) * 2009-08-04 2013-01-10 アミラ ファーマシューティカルス，インコーポレーテッド リゾホスファチジン酸受容体アンタゴニストとしての化合物
PL2481725T3 (pl) 2009-09-25 2015-08-31 Astellas Pharma Inc Podstawiony związek amidowy
GB2474748B (en) * 2009-10-01 2011-10-12 Amira Pharmaceuticals Inc Polycyclic compounds as lysophosphatidic acid receptor antagonists
PH12012500542A1 (en) * 2010-09-24 2012-11-12 Astellas Pharma Inc Substituted amide compound
US8785442B2 (en) * 2011-01-30 2014-07-22 Curegenix, Inc. Compound as antagonist of lysophosphatidic acid receptor, composition, and use thereof
EP2765128A1 (en) * 2013-02-07 2014-08-13 Almirall, S.A. Substituted benzamides with activity towards EP4 receptors
GB201314926D0 (en) * 2013-08-20 2013-10-02 Takeda Pharmaceutical Novel Compounds

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Publication number Priority date Publication date Assignee Title
EP1550461A1 (en) * 2002-06-26 2005-07-06 Ono Pharmaceutical Co., Ltd. Remedy for chronic disease

Non-Patent Citations (5)

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Title
Database registry [Online] Chemical abstracts service, Columbus, OHIO, US; 14 March 2014 (2014-03-14), XP002730139, retrieved from STN Database accession no. 1568813-80-8 abstract *
Database registry [Online] Chemical abstracts service, Columbus, OHIO, US; 21 March 2014 (2014-03-21), XP002730138, retrieved from STN Database accession no. 1571641-85-4 CAS Registry Numbers 1571641-85-4 and 1571236-48-0 *
Database registry [Online] Chemical abstracts service, Columbus, OHIO, US; 25 March 2014 (2014-03-25), XP002730140, retrieved from STN Database accession no. 1573280-07-5 abstract *
Database registry [Online] Chemical abstracts service, Columbus, OHIO, US; 26 March 2014 (2014-03-26), XP002730137, retrieved from STN Database accession no. 1574161-26-4 CAS Registry Numbers 1574161-26-4, 1574158-00-1, 1573850-82-4 and 1573734-63-0 *
Database registry [Online] Chemical abstracts service, columbus, OHIO, US; 28 March 2014 (2014-03-28), XP002730136, retrieved from STN Database accession no. 1575424-65-5 abstract *

Also Published As

Publication number Publication date
MA38854B1 (fr) 2018-05-31
SG11201601250TA (en) 2016-03-30
AR097403A1 (es) 2016-03-09
CL2016000387A1 (es) 2016-12-16
TW201536722A (zh) 2015-10-01
CA2921742A1 (en) 2015-02-26
US20160207880A1 (en) 2016-07-21
KR20160045797A (ko) 2016-04-27
WO2015025164A1 (en) 2015-02-26
US10100018B2 (en) 2018-10-16
JP2016528274A (ja) 2016-09-15
EP3036215A1 (en) 2016-06-29
CN105473548B (zh) 2018-03-23
US20190010129A1 (en) 2019-01-10
AU2014310404B2 (en) 2018-07-12
CR20160084A (es) 2016-05-27
EA201690390A1 (ru) 2016-08-31
MA38854A1 (fr) 2017-07-31
US9464060B2 (en) 2016-10-11
IL243780A0 (en) 2016-04-21
ZA201600753B (en) 2019-07-31
UY35708A (es) 2014-12-31
PH12016500322A1 (en) 2016-05-02
CN105473548A (zh) 2016-04-06
TN2016000061A1 (en) 2017-07-05
GB201314926D0 (en) 2013-10-02
JP6422974B2 (ja) 2018-11-14
US20150057298A1 (en) 2015-02-26
MX2016001896A (es) 2016-05-26
HK1225712A1 (zh) 2017-09-15
AU2014310404A1 (en) 2016-03-10
PE20160284A1 (es) 2016-04-27

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