CA2919572C - Isoindoline or isoquinoline compounds, a process for their preparation and pharmaceutical compositions containing them - Google Patents

Isoindoline or isoquinoline compounds, a process for their preparation and pharmaceutical compositions containing them Download PDF

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Publication number
CA2919572C
CA2919572C CA2919572A CA2919572A CA2919572C CA 2919572 C CA2919572 C CA 2919572C CA 2919572 A CA2919572 A CA 2919572A CA 2919572 A CA2919572 A CA 2919572A CA 2919572 C CA2919572 C CA 2919572C
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CA
Canada
Prior art keywords
tetrahydroisoquinoline
group
methyl
branched
linear
Prior art date
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Application number
CA2919572A
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English (en)
French (fr)
Other versions
CA2919572A1 (en
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
Arnaud Le Tiran
Thierry Le Diguarher
Jean-Michel Henlin
Jerome-Benoit Starck
Anne-Francoise Guillouzic
Guillaume De Nanteuil
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Les Laboratoires Servier SAS
Vernalis R&D Ltd
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Les Laboratoires Servier SAS
Vernalis R&D Ltd
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Publication of CA2919572A1 publication Critical patent/CA2919572A1/en
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Publication of CA2919572C publication Critical patent/CA2919572C/en
Active legal-status Critical Current
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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
    • C07D401/14Heterocyclic 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
    • 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
    • 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

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Immunology (AREA)
  • Biomedical Technology (AREA)
  • Biochemistry (AREA)
  • Pathology (AREA)
  • Radiology & Medical Imaging (AREA)
  • Molecular Biology (AREA)
  • Hematology (AREA)
  • Oncology (AREA)
  • Transplantation (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)
CA2919572A 2013-07-23 2014-07-22 Isoindoline or isoquinoline compounds, a process for their preparation and pharmaceutical compositions containing them Active CA2919572C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR13/57276 2013-07-23
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
PCT/EP2014/065764 WO2015011164A1 (en) 2013-07-23 2014-07-22 New isoindoline or isoquinoline compounds, a process for their preparation and pharmaceutical compositions containing them

Publications (2)

Publication Number Publication Date
CA2919572A1 CA2919572A1 (en) 2015-01-29
CA2919572C true CA2919572C (en) 2017-06-20

Family

ID=49911606

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2919572A Active CA2919572C (en) 2013-07-23 2014-07-22 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 (1) 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)
NZ (1) NZ716155A (enExample)
PE (1) PE20160241A1 (enExample)
PH (1) PH12016500034A1 (enExample)
PL (1) PL3024826T3 (enExample)
PT (1) PT3024826T (enExample)
RS (1) RS58344B1 (enExample)
RU (1) RU2689305C2 (enExample)
SA (1) SA516370439B1 (enExample)
SG (1) SG11201600205XA (enExample)
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
BR112018071548A2 (pt) 2016-04-20 2019-04-16 Bristol-Myers Squibb Company compostos heterocíclicos bicíclicos substituídos
SG11202013026WA (en) 2018-06-27 2021-01-28 Proteostasis Therapeutics Inc Proteasome activity enhancing compounds
EP4059928A4 (en) * 2019-11-15 2023-11-15 Wuhan LL Science and Technology Development Co., Ltd. Rock inhibitor, 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
EP4294513A1 (en) 2021-02-19 2023-12-27 Mevion Medical Systems, Inc. Gantry for a particle therapy system
AR125205A1 (es) * 2021-03-24 2023-06-21 Servier Lab Nuevo proceso para la síntesis de derivados del ácido 5-{5-cloro-2-[(3s)-3-[(morfolin-4-il)metil]-3,4-dihidroisoquinolina-2(1h)-carbonil]fenil}-1,2-dimetil-1h-pirrol-3-carboxílico y su aplicación para la producción de compuestos farmacéuticos
CN119053587A (zh) 2022-02-24 2024-11-29 法国施维雅药厂 5-[7-(3,4-二氢-1h-异喹啉-2-羰基)-1,2,3,4四氢异喹啉-6-基]-1h-吡咯-3-甲酰胺衍生物、含有其的药物组合物及其作为促细胞凋亡剂的用途
PE20251072A1 (es) 2022-05-20 2025-04-10 Novartis Ag Conjugados de anticuerpo-farmaco de compuestos antineoplasicos y metodos de uso de los mismos
CN121001985A (zh) * 2023-03-31 2025-11-21 三井化学株式会社 氨基甲酸酯化合物
WO2025111431A1 (en) 2023-11-22 2025-05-30 Les Laboratoires Servier Anti-cd7 antibody-drug conjugates and methods of use thereof
TW202540185A (zh) 2023-11-22 2025-10-16 法商施維雅藥廠 抗cd74抗體藥物結合物及其使用方法

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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
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US20080227792A1 (en) * 2005-02-15 2008-09-18 Novo Nordisk A/S 3,4-Dihydro-1H-Isoquinoline-2-Carboxylic Acid 5-Aminopyridin-2-Yl Esters
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CN102007101A (zh) 2007-11-30 2011-04-06 生物区科学管理控股有限公司 作为抗菌剂的四氢-异喹啉ppat抑制剂
JP5496915B2 (ja) 2008-02-13 2014-05-21 シージーアイ ファーマシューティカルズ,インコーポレーテッド 6−アリール−イミダゾ[1,2−a]ピラジン誘導体、その製造方法、及びその使用方法
WO2009102463A2 (en) 2008-02-14 2009-08-20 Connor Reynolds Pet waste vacuum system and apparatus, disposable liners therefor, and a method of collecting pet waste using same
WO2012162365A1 (en) * 2011-05-25 2012-11-29 Bristol-Myers Squibb Company Substituted sulfonamides useful as antiapoptotic bcl inhibitors
EP2794591A1 (en) * 2011-12-23 2014-10-29 Novartis AG Compounds for inhibiting the interaction of bcl2 with binding partners
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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
FR3008979B1 (fr) * 2013-07-23 2015-07-24 Servier Lab Nouveaux derives phosphates, 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

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JP2016525529A (ja) 2016-08-25
PL3024826T3 (pl) 2019-05-31
MX2016000904A (es) 2016-04-25
MY193619A (en) 2022-10-20
CA2919572A1 (en) 2015-01-29
ZA201600198B (en) 2019-07-31
CN109456324B (zh) 2022-04-22
MD4793B1 (ro) 2022-02-28
JO3457B1 (ar) 2020-07-05
PH12016500034B1 (en) 2016-03-28
TWI560184B (en) 2016-12-01
DOP2016000009A (es) 2016-03-15
DK3024826T3 (en) 2019-03-04
PH12016500034A1 (en) 2016-03-28
MD4793C1 (ro) 2022-09-30
US20180002313A1 (en) 2018-01-04
MX365373B (es) 2019-05-31
MA38801A1 (fr) 2018-05-31
EA032301B1 (ru) 2019-05-31
CN105431422A (zh) 2016-03-23
CN105431422B (zh) 2019-08-30
UA117490C2 (uk) 2018-08-10
BR112016001080B1 (pt) 2022-04-05
HUE041443T2 (hu) 2019-05-28
IL243449A0 (en) 2016-02-29
RU2689305C2 (ru) 2019-05-27
CU20160010A7 (es) 2016-06-29
US10689364B2 (en) 2020-06-23
RU2016106003A (ru) 2017-08-28
TW201504228A (zh) 2015-02-01
CR20160030A (es) 2016-03-09
AP2016008989A0 (en) 2016-01-31
HK1218754A1 (zh) 2017-03-10
EA201600122A1 (ru) 2016-07-29
HRP20190277T1 (hr) 2019-04-05
EP3024826A1 (en) 2016-06-01
JP6395829B2 (ja) 2018-09-26
EP3024826B1 (en) 2018-11-14
TR201819155T4 (tr) 2019-01-21
ES2711371T3 (es) 2019-05-03
CU24352B1 (es) 2018-07-05
CY1121247T1 (el) 2020-05-29
TN2016000003A1 (en) 2017-07-05
UY35664A (es) 2015-01-30
FR3008977A1 (fr) 2015-01-30
AU2014295101B2 (en) 2018-05-31
RS58344B1 (sr) 2019-03-29
MA38801B1 (fr) 2019-03-29
ME03346B (me) 2019-10-20
AU2014295101A1 (en) 2016-02-04
CN109456324A (zh) 2019-03-12
CL2016000148A1 (es) 2016-08-12
NI201600016A (es) 2016-02-11
NZ716155A (en) 2019-05-31
GEP20207070B (en) 2020-02-25
BR112016001080A2 (enExample) 2017-07-25
SI3024826T1 (sl) 2019-03-29
MD20160018A2 (ro) 2016-07-31
SG11201600205XA (en) 2016-02-26
HK1222856A1 (en) 2017-07-14
US9809574B2 (en) 2017-11-07
LT3024826T (lt) 2019-02-25
KR102008431B1 (ko) 2019-08-07
KR20160033224A (ko) 2016-03-25
AR097009A1 (es) 2016-02-10
US11028070B2 (en) 2021-06-08
SA516370439B1 (ar) 2019-06-27
US20200262816A1 (en) 2020-08-20
US20160194304A1 (en) 2016-07-07
WO2015011164A1 (en) 2015-01-29
PE20160241A1 (es) 2016-04-30
PT3024826T (pt) 2019-01-28

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