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)
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

Links

Classifications

    • 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
    • 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
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/472—Non-condensed isoquinolines, e.g. papaverine
    • A61K31/4725—Non-condensed isoquinolines, e.g. papaverine 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
    • A61K31/496—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
    • A61K31/4965—Non-condensed pyrazines
    • A61K31/497—Non-condensed pyrazines 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
    • A61K31/66—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
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61N—ELECTROTHERAPY; MAGNETOTHERAPY; RADIATION THERAPY; ULTRASOUND THERAPY
    • A61N5/00—Radiation therapy
    • A61N5/10—X-ray therapy; Gamma-ray therapy; Particle-irradiation therapy
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • 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
    • 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
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • 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
    • C07D405/00—Heterocyclic 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
    • C07D405/14—Heterocyclic 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
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic 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
    • C07D417/14—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic 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
    • C07D471/02—Heterocyclic 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
    • C07D471/04—Ortho-condensed systems
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6561—Heterocyclic 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
    • C07F9/65616—Heterocyclic 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)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (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)
  • Radiology & Medical Imaging (AREA)
  • Pathology (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Transplantation (AREA)
  • Oncology (AREA)
  • Hematology (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 (zh)
EP (1) EP3024826B1 (zh)
JP (1) JP6395829B2 (zh)
KR (1) KR102008431B1 (zh)
CN (2) CN109456324B (zh)
AP (1) AP2016008989A0 (zh)
AR (1) AR097009A1 (zh)
AU (1) AU2014295101B2 (zh)
BR (1) BR112016001080B1 (zh)
CA (1) CA2919572C (zh)
CL (1) CL2016000148A1 (zh)
CR (1) CR20160030A (zh)
CU (1) CU24352B1 (zh)
CY (1) CY1121247T1 (zh)
DK (1) DK3024826T3 (zh)
DO (1) DOP2016000009A (zh)
EA (1) EA032301B1 (zh)
ES (1) ES2711371T3 (zh)
FR (1) FR3008977A1 (zh)
GE (1) GEP20207070B (zh)
HK (2) HK1218754A1 (zh)
HR (1) HRP20190277T1 (zh)
HU (1) HUE041443T2 (zh)
IL (1) IL243449A0 (zh)
JO (1) JO3457B1 (zh)
LT (1) LT3024826T (zh)
MA (1) MA38801B1 (zh)
MD (1) MD4793C1 (zh)
ME (1) ME03346B (zh)
MX (1) MX365373B (zh)
MY (1) MY193619A (zh)
NI (1) NI201600016A (zh)
NZ (1) NZ716155A (zh)
PE (1) PE20160241A1 (zh)
PH (1) PH12016500034B1 (zh)
PL (1) PL3024826T3 (zh)
PT (1) PT3024826T (zh)
RS (1) RS58344B1 (zh)
RU (1) RU2689305C2 (zh)
SA (1) SA516370439B1 (zh)
SG (1) SG11201600205XA (zh)
SI (1) SI3024826T1 (zh)
TN (1) TN2016000003A1 (zh)
TR (1) TR201819155T4 (zh)
TW (1) TWI560184B (zh)
UA (1) UA117490C2 (zh)
UY (1) UY35664A (zh)
WO (1) WO2015011164A1 (zh)
ZA (1) ZA201600198B (zh)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
US10851108B2 (en) 2016-04-20 2020-12-01 Bristol-Myers Squibb Company Substituted bicyclic heterocyclic compounds
MA53014A (fr) 2018-06-27 2021-05-05 Proteostasis Therapeutics Inc Composés améliorant l'activité du protéasome
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
AR128587A1 (es) 2022-02-24 2024-05-22 Servier Lab Derivados de 5-[7-(3,4-dihidro-1h-isoquinolina-2-carbonil)-1,2,3,4-tetrahidroisoquinolin-6-il]-1h-pirrol-3-carboxamida, composiciones farmacéuticas que los contienen y sus usos como agentes proapoptóticos
TW202408588A (zh) 2022-05-20 2024-03-01 瑞士商諾華公司 抗體-藥物結合物抗腫瘤化合物及其使用方法

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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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CA2484209C (en) 2002-05-03 2013-06-11 Exelixis, Inc. Protein kinase modulators and methods of use
WO2004096774A1 (en) * 2003-05-01 2004-11-11 Glaxo Group Limited Acyl isoindoline derivatives and acyl isoquinoline derivatives as anti-viral agents
US20050070570A1 (en) 2003-06-18 2005-03-31 4Sc Ag Novel potassium channels modulators
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
WO2006023778A2 (en) * 2004-08-20 2006-03-02 The Regents Of The University Of Michigan Small molecule inhibitors of anti-apoptotic bcl-2 family members and the uses thereof
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
WO2008131000A2 (en) 2007-04-16 2008-10-30 Abbott Laboratories 7-substituted indole mcl-1 inhibitors
CA2707445A1 (en) 2007-11-30 2009-06-11 Biota Scientific Management Pty Ltd 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
CA2859869A1 (en) * 2011-12-23 2013-06-27 Novartis Ag Compounds for inhibiting the interaction of bcl2 with binding partners
US10228738B2 (en) 2011-12-27 2019-03-12 Intel Corporation Methods and systems to control power gates during an active state of a gated domain based on load conditions of the gated domain
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

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012162365A1 (en) * 2011-05-25 2012-11-29 Bristol-Myers Squibb Company Substituted sulfonamides useful as antiapoptotic bcl inhibitors

Also Published As

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

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