CO2017003331A2 - Derivados de imidazol pentacíclicos fusionados - Google Patents

Derivados de imidazol pentacíclicos fusionados

Info

Publication number
CO2017003331A2
CO2017003331A2 CONC2017/0003331A CO2017003331A CO2017003331A2 CO 2017003331 A2 CO2017003331 A2 CO 2017003331A2 CO 2017003331 A CO2017003331 A CO 2017003331A CO 2017003331 A2 CO2017003331 A2 CO 2017003331A2
Authority
CO
Colombia
Prior art keywords
disorders
imidazole derivatives
fused pentacyclic
pentacyclic imidazole
derivatives
Prior art date
Application number
CONC2017/0003331A
Other languages
English (en)
Inventor
Bruno Filocheromme
Haro Garcia Teresa De
Michael Deligny
Jag Paul Heer
Joanna Rachel Quincey
Mengyang Xuan
Zhaoning Zhu
Daniel Christopher Brookings
Mark Daniel Calmiano
Yves Evrard
Martin Clive Hutchings
James Andrew Johnson
Sophie Jadot
Jean Keyaerts
Coss Malcolm Mac
Matthew Duncan Selby
Michael Alan Shaw
Dominique Louis Léon Swinnen
Laurent Schio
Yann Foricher
Original Assignee
Sanofi Sa
Ucb Biopharma Sprl
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 Sanofi Sa, Ucb Biopharma Sprl filed Critical Sanofi Sa
Publication of CO2017003331A2 publication Critical patent/CO2017003331A2/es

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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/08—Bridged systems
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • 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
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • 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
    • A61P25/28—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
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • 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
    • A61P3/00—Drugs for disorders of the metabolism
    • 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
    • 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
    • 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
    • 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
    • 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
    • C07D471/12—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 three hetero rings
    • C07D471/18—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
    • C07D487/18—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
    • C07D491/18—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
    • C07D493/18—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
    • C07D495/18—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
    • C07D513/18—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • 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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Immunology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Pain & Pain Management (AREA)
  • Ophthalmology & Optometry (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Transplantation (AREA)
  • Rheumatology (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

Una serie de derivados de imidazol pentacíclicos fusionados, que son potentes moduladores de la actividad de TNFα humano, son en consecuencia beneficiosos en el tratamiento y/o prevención de diferentes enfermedades humanas, que incluyen trastornos autoinmunológicos e inflamatorios; trastornos neurológicos y neurodegenerativos; trastornos de dolor y nociceptivos; trastornos cardiovasculares; trastornos metabólicos; trastornos oculares; y trastornos oncológicos. En particular, la presente invención se relaciona con derivados de 6,7- dihidro-7,14-metanobencimidazo[1,2-b][2,5]benzodiazocin-5(14H)-ona y análogos de los mismos.
CONC2017/0003331A 2014-10-03 2017-04-06 Derivados de imidazol pentacíclicos fusionados CO2017003331A2 (es)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP14290299 2014-10-03
EP15162641 2015-04-07
EP15171036 2015-06-08
PCT/EP2015/072868 WO2016050975A1 (en) 2014-10-03 2015-10-02 Fused pentacyclic imidazole derivatives

Publications (1)

Publication Number Publication Date
CO2017003331A2 true CO2017003331A2 (es) 2017-09-29

Family

ID=54238452

Family Applications (1)

Application Number Title Priority Date Filing Date
CONC2017/0003331A CO2017003331A2 (es) 2014-10-03 2017-04-06 Derivados de imidazol pentacíclicos fusionados

Country Status (36)

Country Link
US (3) US10202405B2 (es)
EP (1) EP3201196B1 (es)
JP (1) JP6629847B2 (es)
KR (1) KR102442235B1 (es)
CN (1) CN107108672B (es)
AP (1) AP2017009809A0 (es)
AU (1) AU2015326798B2 (es)
BR (1) BR112017006669B1 (es)
CA (1) CA2962826C (es)
CL (1) CL2017000787A1 (es)
CO (1) CO2017003331A2 (es)
CR (1) CR20170167A (es)
DK (1) DK3201196T3 (es)
EA (1) EA032839B1 (es)
EC (1) ECSP17027306A (es)
ES (1) ES2885432T3 (es)
GT (1) GT201700044A (es)
HR (1) HRP20211605T1 (es)
HU (1) HUE056133T2 (es)
IL (1) IL251147B (es)
LT (1) LT3201196T (es)
MA (1) MA40770B1 (es)
MX (1) MX2017004201A (es)
MY (1) MY181019A (es)
PE (1) PE20170693A1 (es)
PH (1) PH12017500414B1 (es)
PL (1) PL3201196T3 (es)
RS (1) RS62423B1 (es)
SG (1) SG11201701796XA (es)
SI (1) SI3201196T1 (es)
TN (1) TN2017000083A1 (es)
TW (1) TWI719949B (es)
UA (1) UA120764C2 (es)
UY (1) UY36341A (es)
WO (1) WO2016050975A1 (es)
ZA (1) ZA201701946B (es)

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HUE056133T2 (hu) * 2014-10-03 2022-01-28 UCB Biopharma SRL Fuzionált pentaciklusos imidazol-származékok
AR104291A1 (es) 2015-04-17 2017-07-12 Abbvie Inc Moduladores tricíclicos de la señalización por tnf
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WO2016168638A1 (en) 2015-04-17 2016-10-20 Abbvie Inc. Indazolones as modulators of tnf signaling
GB201510758D0 (en) 2015-06-18 2015-08-05 Ucb Biopharma Sprl Novel TNFa structure for use in therapy
EP3436460B1 (en) 2016-04-01 2021-08-18 UCB Biopharma SRL Fused pentacyclic imidazole derivatives as modulators of tnf activity
JP6968089B2 (ja) * 2016-04-01 2021-11-17 ユーシービー バイオファルマ エスアールエル Ｔｎｆ活性のモジュレーターとしての縮合六環式イミダゾール誘導体
WO2017167996A1 (en) 2016-04-01 2017-10-05 Ucb Biopharma Sprl Fused pentacyclic imidazole derivatives as modulators of tnf activity
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CA3055863A1 (en) * 2017-03-15 2018-09-20 Ucb Biopharma Sprl Fused pentacyclic imidazole derivatives as modulators of tnf activity
LT3615534T (lt) * 2017-04-25 2021-11-25 UCB Biopharma SRL Sulieti pentacikliniai imidazolo dariniai kaip tnf aktyvumo moduliatoriai
WO2020084008A1 (en) 2018-10-24 2020-04-30 UCB Biopharma SRL Fused pentacyclic imidazole derivatives as modulators of tnf activity
CN113683505A (zh) * 2021-09-29 2021-11-23 厦门大华本安化工安全研究院有限公司 一种含氧代环丁基的羧酸酯类化合物的制备方法

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BR112017006669B1 (pt) 2023-04-18
EP3201196A1 (en) 2017-08-09
EA201790734A1 (ru) 2017-09-29
MX2017004201A (es) 2017-05-30
AU2015326798A1 (en) 2017-04-06
EP3201196B1 (en) 2021-07-28
HUE056133T2 (hu) 2022-01-28
DK3201196T3 (da) 2021-09-06
AP2017009809A0 (en) 2017-03-31
KR102442235B1 (ko) 2022-09-08
PE20170693A1 (es) 2017-06-13
AU2015326798B2 (en) 2020-01-02
CN107108672A (zh) 2017-08-29
BR112017006669A2 (pt) 2017-12-26
IL251147B (en) 2020-05-31
TWI719949B (zh) 2021-03-01
WO2016050975A1 (en) 2016-04-07
GT201700044A (es) 2019-09-09
CA2962826C (en) 2023-08-08
MY181019A (en) 2020-12-16
ES2885432T3 (es) 2021-12-13
JP2017531648A (ja) 2017-10-26
HRP20211605T1 (hr) 2022-01-21
RS62423B1 (sr) 2021-10-29
KR20170068503A (ko) 2017-06-19
ZA201701946B (en) 2018-07-25
NZ730256A (en) 2021-05-28
CL2017000787A1 (es) 2017-11-24
MA40770A (fr) 2021-03-24
PL3201196T3 (pl) 2022-01-03
SG11201701796XA (en) 2017-04-27
TN2017000083A1 (en) 2018-07-04
US20210155637A1 (en) 2021-05-27
LT3201196T (lt) 2021-09-27
CA2962826A1 (en) 2016-04-07
SI3201196T1 (sl) 2021-12-31
MA40770B1 (fr) 2021-11-30
TW201629067A (zh) 2016-08-16
PH12017500414A1 (en) 2017-07-17
PH12017500414B1 (en) 2017-07-17
JP6629847B2 (ja) 2020-01-15
UA120764C2 (uk) 2020-02-10
US11912721B2 (en) 2024-02-27
IL251147A0 (en) 2017-04-30
CR20170167A (es) 2017-08-10
US10906919B2 (en) 2021-02-02
CN107108672B (zh) 2019-11-08
US20190367535A1 (en) 2019-12-05
US10202405B2 (en) 2019-02-12
ECSP17027306A (es) 2017-05-31
EA032839B1 (ru) 2019-07-31
UY36341A (es) 2016-04-29
US20170305932A1 (en) 2017-10-26

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