CA2983668C - Pyrazole derivatives useful as 5-lipoxygenase activating protein (flap) inhibitors - Google Patents

Pyrazole derivatives useful as 5-lipoxygenase activating protein (flap) inhibitors Download PDF

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CA2983668C
CA2983668C CA2983668A CA2983668A CA2983668C CA 2983668 C CA2983668 C CA 2983668C CA 2983668 A CA2983668 A CA 2983668A CA 2983668 A CA2983668 A CA 2983668A CA 2983668 C CA2983668 C CA 2983668C
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mmol
pyrazol
reaction mixture
methy1
et0ac
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French (fr)
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CA2983668A1 (en
Inventor
Johan Olof Broddefalk
Hans Fredrik Emtenas
Kenneth Lars Granberg
Malin Anita Lemurell
Daniel Tor Pettersen
Alleyn Thomas Plowright
Lars Johan Andreas Ulander
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AstraZeneca AB
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AstraZeneca AB
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D231/00Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/38Nitrogen atoms
    • C07D231/40Acylated on said nitrogen atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02Heterocyclic 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
    • C07D487/04Ortho-condensed systems
    • 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
    • A61K31/41Heterocyclic 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
    • A61K31/4151,2-Diazoles
    • A61K31/41551,2-Diazoles non condensed and 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
    • A61K31/4985Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00Drugs for disorders of the urinary system
    • A61P13/12Drugs for disorders of the urinary system of the kidneys
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/08Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • 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
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/10Drugs 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D231/00Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/44Oxygen and nitrogen or sulfur and nitrogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D231/00Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/44Oxygen and nitrogen or sulfur and nitrogen atoms
    • C07D231/46Oxygen atom in position 3 or 5 and nitrogen atom in position 4
    • C07D231/50Acylated on said nitrogen atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D417/02Heterocyclic 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 two hetero rings
    • C07D417/12Heterocyclic 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 two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D498/00Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Epidemiology (AREA)
  • Urology & Nephrology (AREA)
  • Diabetes (AREA)
  • Vascular Medicine (AREA)
  • Pulmonology (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
CA2983668A 2015-05-04 2016-05-03 Pyrazole derivatives useful as 5-lipoxygenase activating protein (flap) inhibitors Active CA2983668C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201562156424P 2015-05-04 2015-05-04
US62/156424 2015-05-04
PCT/EP2016/059848 WO2016177703A1 (en) 2015-05-04 2016-05-03 Pyrazole derivatives useful as 5-lipoxygenase activating protein (flap) inhibitors

Publications (2)

Publication Number Publication Date
CA2983668A1 CA2983668A1 (en) 2016-11-10
CA2983668C true CA2983668C (en) 2023-06-27

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CA2983668A Active CA2983668C (en) 2015-05-04 2016-05-03 Pyrazole derivatives useful as 5-lipoxygenase activating protein (flap) inhibitors

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US (6) US10183947B2 (https=)
EP (2) EP3292105B1 (https=)
JP (1) JP6564062B2 (https=)
KR (1) KR102623474B1 (https=)
CN (1) CN107646036B (https=)
AR (1) AR104512A1 (https=)
AU (1) AU2016258874B2 (https=)
BR (1) BR112017022757B1 (https=)
CA (1) CA2983668C (https=)
CL (1) CL2017002660A1 (https=)
CO (1) CO2017011506A2 (https=)
CR (1) CR20170513A (https=)
CY (2) CY1122689T1 (https=)
DK (2) DK3292105T3 (https=)
DO (1) DOP2017000244A (https=)
EA (1) EA032221B1 (https=)
ES (2) ES2902139T3 (https=)
GT (1) GT201700220A (https=)
HR (2) HRP20192172T1 (https=)
HU (2) HUE056875T2 (https=)
IL (1) IL255069B (https=)
LT (1) LT3670499T (https=)
ME (1) ME03663B (https=)
MX (1) MX372755B (https=)
MY (1) MY186647A (https=)
PE (1) PE20180247A1 (https=)
PH (1) PH12017502112B1 (https=)
PL (2) PL3670499T3 (https=)
PT (2) PT3292105T (https=)
RS (2) RS59671B1 (https=)
SG (1) SG11201708558RA (https=)
SI (2) SI3670499T1 (https=)
SM (2) SMT202100722T1 (https=)
SV (1) SV2017005549A (https=)
TN (1) TN2017000458A1 (https=)
TW (1) TWI718146B (https=)
WO (1) WO2016177703A1 (https=)
ZA (1) ZA201708189B (https=)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AR104512A1 (es) 2015-05-04 2017-07-26 Astrazeneca Ab Compuestos de pirazol inhibidores de proteĆ­na activadora de 5-lipoxigenasa (flap)
CN109890385B (zh) * 2016-10-28 2022-08-02 é˜æę–Æåˆ©åŗ·(ē‘žå…ø)ęœ‰é™å…¬åø (1r,2r)-2-[4-(3-ē”²åŸŗ-1h-吔唑-5-基)č‹Æē”²é…°åŸŗ]-n-(4-氧代-4,5,6,7-四氢吔唑并[1,5-a]吔嗪-3-基)ēŽÆå·±ēƒ·ē”²é…°čƒŗēš„ē»“ę™¶å½¢å¼
GB201905721D0 (en) 2019-04-24 2019-06-05 Univ Dundee Compounds
CN110169969B (zh) * 2019-06-28 2022-05-27 å—äŗ¬åŒ»ē§‘å¤§å­¦ Mk571åœØåˆ¶å¤‡é¢„é˜²å’Œę²»ē–—åæƒč„ē—…čÆē‰©äø­åŗ”ē”Ø
CN111084775A (zh) * 2020-02-17 2020-05-01 ē‰”äø¹ę±ŸåŒ»å­¦é™¢ äø€ē§ē”ØäŗŽę²»ē–—ē™«ē—«ēš„čÆē‰©ē»„åˆē‰©
CN111419800B (zh) * 2020-04-23 2021-03-19 ęø©å·žåŒ»ē§‘å¤§å­¦é™„å±žē¬¬äŗŒåŒ»é™¢ć€ęø©å·žåŒ»ē§‘å¤§å­¦é™„å±žč‚²č‹±å„æē«„åŒ»é™¢ ē”ØäŗŽę²»ē–—ēŗ¢ę–‘ē‹¼ē–®ēš„čÆē‰©åˆ¶å‰‚åŠå…¶åˆ¶å¤‡ę–¹ę³•
CN111643498B (zh) * 2020-07-20 2021-05-07 é»‘é¾™ę±Ÿäø­åŒ»čÆå¤§å­¦ äø€ē§ę²»ē–—č‚¾ē»“ēŸ³ēš„čÆē‰©ē»„åˆē‰©åŠå…¶ē”Øé€”
CN111714499B (zh) * 2020-07-27 2021-05-11 é»‘é¾™ę±Ÿäø­åŒ»čÆå¤§å­¦ äø€ē§ē”ØäŗŽę²»ē–—å¤šå›Šåµå·¢ē»¼åˆå¾ēš„čÆē‰©ē»„åˆē‰©

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AP9400632A0 (en) 1993-04-29 1995-10-07 Zeneca Ltd Ether derivatives.
US5773422A (en) 1996-01-29 1998-06-30 Komer; Gene Avermectin formulation
EP1670804A2 (en) * 2003-09-10 2006-06-21 GPC Biotech AG Heterobicyclic compounds as pharmaceutically active agents
GB2431927B (en) 2005-11-04 2010-03-17 Amira Pharmaceuticals Inc 5-Lipoxygenase-activating protein (FLAP) inhibitors
TW200815351A (en) * 2006-05-02 2008-04-01 Astrazeneca Ab Novel compounds
JP2010518025A (ja) 2007-02-05 2010-05-27 ć‚¢ćƒŸćƒ© ćƒ•ć‚”ćƒ¼ćƒžć‚·ćƒ„ćƒ¼ćƒ†ć‚£ć‚«ćƒ«ć‚¹ļ¼Œć‚¤ćƒ³ć‚³ćƒ¼ćƒćƒ¬ćƒ¼ćƒ†ćƒƒćƒ‰ ļ¼•āˆ’ćƒŖćƒć‚­ć‚·ć‚²ćƒŠćƒ¼ć‚¼ę“»ę€§åŒ–ć‚æćƒ³ćƒ‘ć‚Æč³Ŗļ¼ˆļ½†ļ½Œļ½ļ½ļ¼‰ć‚¤ćƒ³ćƒ’ćƒ“ć‚æćƒ¼ćØć—ć¦ć®é€†ć‚¤ćƒ³ćƒ‰ćƒ¼ćƒ«
GB0702456D0 (en) * 2007-02-08 2007-03-21 Astrazeneca Ab New combination
CA2684618A1 (en) * 2007-04-20 2008-10-30 Schering Corporation Tetrahydropyrido[4,3-d]pyrimidinone derivatives and methods of use thereof
US9096546B2 (en) * 2007-05-10 2015-08-04 Albany Molecular Research, Inc. Aryl- and heteroaryl-substituted tetrahydrobenzo-1,4-diazepines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin
WO2009045700A2 (en) 2007-10-05 2009-04-09 Amira Pharmaceuticals, Inc. 5-lipoxygenase-activating protein (flap) inhibitors
AR104512A1 (es) * 2015-05-04 2017-07-26 Astrazeneca Ab Compuestos de pirazol inhibidores de proteĆ­na activadora de 5-lipoxigenasa (flap)

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US20200157113A1 (en) 2020-05-21
RS62729B1 (sr) 2022-01-31
EP3292105B1 (en) 2019-10-02
IL255069A0 (en) 2017-12-31
TN2017000458A1 (en) 2019-04-12
DK3292105T3 (da) 2019-12-09
JP2018514535A (ja) 2018-06-07
SI3292105T1 (sl) 2020-01-31
CA2983668A1 (en) 2016-11-10
DK3670499T3 (da) 2022-01-03
MX2017013571A (es) 2018-02-26
PH12017502112B1 (en) 2021-07-02
PL3292105T3 (pl) 2020-04-30
TW201713625A (zh) 2017-04-16
JP6564062B2 (ja) 2019-08-21
US20230219967A1 (en) 2023-07-13
HRP20211993T1 (hr) 2022-04-01
MY186647A (en) 2021-08-03
CN107646036B (zh) 2020-05-19
EA032221B1 (ru) 2019-04-30
US12024523B2 (en) 2024-07-02
SI3670499T1 (sl) 2022-02-28
US11691978B2 (en) 2023-07-04
US10508119B2 (en) 2019-12-17
RS59671B1 (sr) 2020-01-31
SMT201900691T1 (it) 2020-01-14
US20210355127A1 (en) 2021-11-18
AR104512A1 (es) 2017-07-26
NZ737672A (en) 2020-11-27
MX372755B (es) 2020-06-29
HK1245255A1 (en) 2018-08-24
CY1125179T1 (el) 2023-03-24
KR20180002784A (ko) 2018-01-08
PT3670499T (pt) 2021-12-24
EP3292105A1 (en) 2018-03-14
EA201792341A1 (ru) 2018-05-31
ME03663B (me) 2020-07-20
US11001589B2 (en) 2021-05-11
TWI718146B (zh) 2021-02-11
AU2016258874A1 (en) 2017-12-14
BR112017022757B1 (pt) 2023-02-23
LT3670499T (lt) 2021-12-27
PH12017502112A1 (en) 2018-05-07
US20240317767A1 (en) 2024-09-26
KR102623474B1 (ko) 2024-01-09
US20180237439A1 (en) 2018-08-23
ES2902139T3 (es) 2022-03-25
PT3292105T (pt) 2019-12-13
SG11201708558RA (en) 2017-11-29
SMT202100722T1 (it) 2022-01-10
CN107646036A (zh) 2018-01-30
ES2760466T3 (es) 2020-05-14
US10183947B2 (en) 2019-01-22
HUE047445T2 (hu) 2020-04-28
BR112017022757A2 (pt) 2018-07-17
AU2016258874B2 (en) 2020-04-30
SV2017005549A (es) 2018-03-12
ZA201708189B (en) 2018-11-28
HUE056875T2 (hu) 2022-03-28
CR20170513A (es) 2018-02-13
CL2017002660A1 (es) 2018-04-13
EP3670499B1 (en) 2021-09-29
EP3670499A1 (en) 2020-06-24
WO2016177703A1 (en) 2016-11-10
GT201700220A (es) 2018-12-19
CO2017011506A2 (es) 2018-01-31
US20190084991A1 (en) 2019-03-21
CY1122689T1 (el) 2021-03-12
PE20180247A1 (es) 2018-02-02
HRP20192172T1 (hr) 2020-02-21
DOP2017000244A (es) 2017-11-15
IL255069B (en) 2019-12-31
PL3670499T3 (pl) 2022-02-14

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