TWI560184B - New isoindoline or isoquinoline compounds, a process for their preparation and pharmaceutical compositions containing them - Google Patents

New isoindoline or isoquinoline compounds, a process for their preparation and pharmaceutical compositions containing them

Info

Publication number
TWI560184B
TWI560184B TW103125161A TW103125161A TWI560184B TW I560184 B TWI560184 B TW I560184B TW 103125161 A TW103125161 A TW 103125161A TW 103125161 A TW103125161 A TW 103125161A TW I560184 B TWI560184 B TW I560184B
Authority
TW
Taiwan
Prior art keywords
preparation
pharmaceutical compositions
compositions containing
isoquinoline compounds
new isoindoline
Prior art date
Application number
TW103125161A
Other languages
English (en)
Chinese (zh)
Other versions
TW201504228A (zh
Inventor
James Edward Paul Davidson
James Brooke Murray
I-Jen Chen
Claire Walmsley
Mark Dodsworth
Johannes W G Meissner
Paul Brough
Imre Fejes
Janos Tatai
Miklos Nyerges
Andras Kotschy
Zoltan Szlavik
Olivier Geneste
Tiran Arnaud Le
Diguarher Thierry Le
Jean-Michel Henlin
Jerome-Benoit Starck
Anne-Francoise Guillouzic
Nanteuil Guillaume De
Original Assignee
Servier Lab
Vernalis R&D Ltd
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 Servier Lab, Vernalis R&D Ltd filed Critical Servier Lab
Publication of TW201504228A publication Critical patent/TW201504228A/zh
Application granted granted Critical
Publication of TWI560184B publication Critical patent/TWI560184B/zh

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic 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
    • C07D401/02Heterocyclic 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
    • C07D401/04Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic 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
    • C07D401/14Heterocyclic 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic 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
    • A61K31/47Quinolines; Isoquinolines
    • A61K31/472Non-condensed isoquinolines, e.g. papaverine
    • A61K31/4725Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495Heterocyclic 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
    • A61K31/496Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495Heterocyclic 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
    • A61K31/4965Non-condensed pyrazines
    • A61K31/497Non-condensed pyrazines containing further heterocyclic rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535Heterocyclic 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
    • A61K31/53751,4-Oxazines, e.g. morpholine
    • A61K31/53771,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/66Phosphorus compounds
    • A61K31/675Phosphorus compounds having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61NELECTROTHERAPY; MAGNETOTHERAPY; RADIATION THERAPY; ULTRASOUND THERAPY
    • A61N5/00Radiation therapy
    • A61N5/10X-ray therapy; Gamma-ray therapy; Particle-irradiation therapy
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • A61P35/02Antineoplastic agents specific for leukemia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/02Immunomodulators
    • A61P37/06Immunosuppressants, e.g. drugs for graft rejection
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic 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
    • C07D405/14Heterocyclic 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 three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic 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
    • C07D417/14Heterocyclic 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 three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6561Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
    • C07F9/65616Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system having three or more than three double bonds between ring members or between ring members and non-ring members, e.g. purine or analogs

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Immunology (AREA)
  • Biomedical Technology (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Pathology (AREA)
  • Radiology & Medical Imaging (AREA)
  • Transplantation (AREA)
  • Hematology (AREA)
  • Oncology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Indole Compounds (AREA)
TW103125161A 2013-07-23 2014-07-22 New isoindoline or isoquinoline compounds, a process for their preparation and pharmaceutical compositions containing them TWI560184B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR1357276A FR3008977A1 (fr) 2013-07-23 2013-07-23 Nouveaux derives d'isoindoline ou d'isoquinoline, leur procede de preparation et les compositions pharmaceutiques qui les contiennent

Publications (2)

Publication Number Publication Date
TW201504228A TW201504228A (zh) 2015-02-01
TWI560184B true TWI560184B (en) 2016-12-01

Family

ID=49911606

Family Applications (1)

Application Number Title Priority Date Filing Date
TW103125161A TWI560184B (en) 2013-07-23 2014-07-22 New isoindoline or isoquinoline compounds, a process for their preparation and pharmaceutical compositions containing them

Country Status (49)

Country Link
US (3) US9809574B2 (enExample)
EP (1) EP3024826B1 (enExample)
JP (1) JP6395829B2 (enExample)
KR (1) KR102008431B1 (enExample)
CN (2) CN109456324B (enExample)
AP (1) AP2016008989A0 (enExample)
AR (1) AR097009A1 (enExample)
AU (1) AU2014295101B2 (enExample)
BR (1) BR112016001080B1 (enExample)
CA (1) CA2919572C (enExample)
CL (1) CL2016000148A1 (enExample)
CR (1) CR20160030A (enExample)
CU (1) CU24352B1 (enExample)
CY (1) CY1121247T1 (enExample)
DK (1) DK3024826T3 (enExample)
DO (1) DOP2016000009A (enExample)
EA (1) EA032301B1 (enExample)
ES (1) ES2711371T3 (enExample)
FR (1) FR3008977A1 (enExample)
GE (2) GEP20207070B (enExample)
HK (1) HK1218754A1 (enExample)
HR (1) HRP20190277T1 (enExample)
HU (1) HUE041443T2 (enExample)
IL (1) IL243449A0 (enExample)
JO (1) JO3457B1 (enExample)
LT (1) LT3024826T (enExample)
MA (1) MA38801B1 (enExample)
MD (1) MD4793C1 (enExample)
ME (1) ME03346B (enExample)
MX (1) MX365373B (enExample)
MY (1) MY193619A (enExample)
NI (1) NI201600016A (enExample)
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PE (1) PE20160241A1 (enExample)
PH (1) PH12016500034A1 (enExample)
PL (1) PL3024826T3 (enExample)
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RS (1) RS58344B1 (enExample)
RU (1) RU2689305C2 (enExample)
SA (1) SA516370439B1 (enExample)
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SI (1) SI3024826T1 (enExample)
TN (1) TN2016000003A1 (enExample)
TR (1) TR201819155T4 (enExample)
TW (1) TWI560184B (enExample)
UA (1) UA117490C2 (enExample)
UY (1) UY35664A (enExample)
WO (1) WO2015011164A1 (enExample)
ZA (1) ZA201600198B (enExample)

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FR3008977A1 (fr) * 2013-07-23 2015-01-30 Servier Lab Nouveaux derives d'isoindoline ou d'isoquinoline, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
EA037300B1 (ru) 2016-04-20 2021-03-05 Бристол-Маерс Сквибб Компани Замещенные бициклические гетероциклические соединения
AU2019295765B2 (en) 2018-06-27 2024-08-29 Yumanity, Inc. Proteasome activity enhancing compounds
CA3158241A1 (en) * 2019-11-15 2021-05-20 Wuhan Ll Science And Technology Development Co., Ltd. Rock inhibitor and preparation method therefor and use thereof
CN112010796B (zh) * 2020-09-17 2022-04-22 浙江大学 光学活性3-(1,1-二氟-2-氧-2-芳基乙基)异吲哚啉-1-酮衍生物制备方法
US12245355B2 (en) 2021-02-19 2025-03-04 Mevion Medical Systems, Inc. Gantry for a particle therapy system
EP4313964A1 (en) * 2021-03-24 2024-02-07 Les Laboratoires Servier New process for the synthesis of 5-{5-chloro-2-[(3s)-3- [(morpholin-4-yl)methyl]-3,4-dihydroisoquinoline-2(1h )-carbonyl]phenyl}-1,2-dimethyl-1h-pyrrole-3-carboxylic acid derivatives and its application for the production of pharmaceutical compounds
JP2025508803A (ja) 2022-02-24 2025-04-10 レ ラボラトワール セルヴィエ 5-[7-(3,4-ジヒドロ-1h-イソキノリン-2-カルボニル)-1,2,3,4-テトラヒドロイソキノリン-6-イル]-1h-ピロール-3-カルボキサミド誘導体、それを含有する医薬組成物及びアポトーシス促進剤としてのその使用
PE20251072A1 (es) 2022-05-20 2025-04-10 Novartis Ag Conjugados de anticuerpo-farmaco de compuestos antineoplasicos y metodos de uso de los mismos
KR20250149173A (ko) * 2023-03-31 2025-10-15 미쓰이 가가쿠 가부시키가이샤 카바메이트 화합물
TW202540186A (zh) 2023-11-22 2025-10-16 瑞士商諾華公司 抗cd7抗體藥物結合物及其使用方法
PY24103486A (es) 2023-11-22 2025-06-06 Servier Lab Conjugados de anticuerpo anti-cd74-fármaco y métodos de uso de los mismos

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WO2012162365A1 (en) * 2011-05-25 2012-11-29 Bristol-Myers Squibb Company Substituted sulfonamides useful as antiapoptotic bcl inhibitors

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US20050070570A1 (en) 2003-06-18 2005-03-31 4Sc Ag Novel potassium channels modulators
US8557812B2 (en) * 2004-08-20 2013-10-15 The Regents Of The University Of Michigan Small molecule inhibitors of anti-apoptotic BCL-2 family members and the uses thereof
CN101039662A (zh) * 2004-08-20 2007-09-19 密执安州立大学董事会 抗-细胞凋亡bcl-2家族成员的小分子抑制剂及其应用
RU2007128987A (ru) * 2005-02-15 2009-03-27 Ново Нордиск А/С (DK) 3,4-дигидро-1н-изохинолин-2-карбоновой кислоты 5-аминопиридин-2-2-иловые эфиры
ES2705599T3 (es) 2007-04-16 2019-03-26 Abbvie Inc Indoles sustituidos en la posición 7 como inhibidores de mcl-1
WO2009073545A2 (en) 2007-11-30 2009-06-11 Maxthera, Inc. Tetrahydro-isoquinoline ppat inhibitors as antibacterial agents
NZ587039A (en) 2008-02-13 2013-01-25 Gilead Connecticut Inc 6-aryl-imidazo[1, 2-a]pyrazine derivatives, method of making, and method of use thereof
US7984530B2 (en) 2008-02-14 2011-07-26 Tory Reynolds Pet waste vacuum system and apparatus, disposable liners therefor, and a method of collecting pet waste using same
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FR2986002B1 (fr) * 2012-01-24 2014-02-21 Servier Lab Nouveaux derives d'indolizine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
FR3008977A1 (fr) * 2013-07-23 2015-01-30 Servier Lab Nouveaux derives d'isoindoline ou d'isoquinoline, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
FR3008979B1 (fr) * 2013-07-23 2015-07-24 Servier Lab Nouveaux derives phosphates, leur procede de preparation et les compositions pharmaceutiques qui les contiennent

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Also Published As

Publication number Publication date
MX365373B (es) 2019-05-31
MX2016000904A (es) 2016-04-25
FR3008977A1 (fr) 2015-01-30
RU2689305C2 (ru) 2019-05-27
PH12016500034B1 (en) 2016-03-28
PT3024826T (pt) 2019-01-28
IL243449A0 (en) 2016-02-29
SG11201600205XA (en) 2016-02-26
DK3024826T3 (en) 2019-03-04
MA38801B1 (fr) 2019-03-29
CA2919572C (en) 2017-06-20
TW201504228A (zh) 2015-02-01
JP6395829B2 (ja) 2018-09-26
CN105431422B (zh) 2019-08-30
ME03346B (me) 2019-10-20
PH12016500034A1 (en) 2016-03-28
HK1218754A1 (zh) 2017-03-10
US9809574B2 (en) 2017-11-07
ES2711371T3 (es) 2019-05-03
AP2016008989A0 (en) 2016-01-31
RU2016106003A (ru) 2017-08-28
NZ716155A (en) 2019-05-31
JO3457B1 (ar) 2020-07-05
EP3024826B1 (en) 2018-11-14
MD4793B1 (ro) 2022-02-28
EP3024826A1 (en) 2016-06-01
MY193619A (en) 2022-10-20
CN105431422A (zh) 2016-03-23
US20160194304A1 (en) 2016-07-07
AU2014295101B2 (en) 2018-05-31
CR20160030A (es) 2016-03-09
MA38801A1 (fr) 2018-05-31
KR102008431B1 (ko) 2019-08-07
SA516370439B1 (ar) 2019-06-27
CY1121247T1 (el) 2020-05-29
US20200262816A1 (en) 2020-08-20
MD20160018A2 (ro) 2016-07-31
NI201600016A (es) 2016-02-11
UA117490C2 (uk) 2018-08-10
SI3024826T1 (sl) 2019-03-29
TN2016000003A1 (en) 2017-07-05
DOP2016000009A (es) 2016-03-15
TR201819155T4 (tr) 2019-01-21
CU24352B1 (es) 2018-07-05
CA2919572A1 (en) 2015-01-29
MD4793C1 (ro) 2022-09-30
US20180002313A1 (en) 2018-01-04
EA201600122A1 (ru) 2016-07-29
CU20160010A7 (es) 2016-06-29
GEAP201914063A (en) 2019-10-25
GEP20207070B (en) 2020-02-25
PL3024826T3 (pl) 2019-05-31
RS58344B1 (sr) 2019-03-29
AR097009A1 (es) 2016-02-10
JP2016525529A (ja) 2016-08-25
HK1222856A1 (en) 2017-07-14
UY35664A (es) 2015-01-30
CL2016000148A1 (es) 2016-08-12
BR112016001080A2 (enExample) 2017-07-25
AU2014295101A1 (en) 2016-02-04
HUE041443T2 (hu) 2019-05-28
LT3024826T (lt) 2019-02-25
US11028070B2 (en) 2021-06-08
WO2015011164A1 (en) 2015-01-29
KR20160033224A (ko) 2016-03-25
PE20160241A1 (es) 2016-04-30
EA032301B1 (ru) 2019-05-31
US10689364B2 (en) 2020-06-23
ZA201600198B (en) 2019-07-31
CN109456324B (zh) 2022-04-22
HRP20190277T1 (hr) 2019-04-05
BR112016001080B1 (pt) 2022-04-05
CN109456324A (zh) 2019-03-12

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