AR097403A1 - Derivados de benzamida como antagonistas de lpar1 y/o lpar5 y un proceso para su preparación - Google Patents

Derivados de benzamida como antagonistas de lpar1 y/o lpar5 y un proceso para su preparación

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Publication number
AR097403A1
AR097403A1 ARP140103129A ARP140103129A AR097403A1 AR 097403 A1 AR097403 A1 AR 097403A1 AR P140103129 A ARP140103129 A AR P140103129A AR P140103129 A ARP140103129 A AR P140103129A AR 097403 A1 AR097403 A1 AR 097403A1
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Argentina
Prior art keywords
alkyl
saturated
group
independently represent
hydrogen atom
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ARP140103129A
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English (en)
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Takeda Pharmaceuticals Co
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Publication of AR097403A1 publication Critical patent/AR097403A1/es

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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • 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
    • A61K31/275—Nitriles; Isonitriles
    • A61K31/277—Nitriles; Isonitriles having a ring, e.g. verapamil
    • 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • 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
    • 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
    • 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
    • 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
    • A61P9/10—Drugs 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/46—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/52—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/54—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and etherified hydroxy groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/04—Systems containing only non-condensed rings with a four-membered ring

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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)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Urology & Nephrology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Vascular Medicine (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Cardiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Peptides Or Proteins (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Los procesos para su preparación, composiciones farmacéuticas que los contienen y su uso en terapias de enfermedades vinculadas con la actividad de LPAR1. Reivindicación 1: Un compuesto de fórmula (1) caracterizado porque R¹ representa un grupo arilo C₅₋₁₀; sustituido por al menos un sustituyente seleccionado de halógeno, ciano, nitro, carboxilo, hidroxilo, cicloalquilo C₃₋₆, alcoxi C₁₋₆, alcoxicarbonilo C₁₋₆, alcoxicarbonilamino C₁₋₆, haloalcoxi C₁₋₆, -NR⁵R⁶, cicloalquilamino C₃₋₆, alquiltio C₁₋₆, alquilcarbonilo C₁₋₆, alquilcarboniloxi C₁₋₆, alquilcarbonilamino C₁₋₆, sulfonamido, alquilsulfonilo C₁₋₆, alquilsulfonilamino C₁₋₆, -C(O)NR⁷R⁸, alquilo C₁₋₆, el cual grupo alquilo puede estar opcionalmente sustituido a su vez por al menos un halógeno, hidroxilo, carboxilo o grupo alcoxicarbonilo C₁₋₆ y un anillo de 5 a 6 miembros saturado o insaturado, que puede comprender al menos un heteroátomo del anillo seleccionado de nitrógeno, oxígeno y azufre, y el anillo en sí mismo esta opcionalmente sustituido por al menos un sustituyente seleccionado de halógeno, hidroxilo, oxo, carboxilo, ciano, alquilo C₁₋₆, alcoxicarbonilo C₁₋₆ e hidroxialquilo C₁₋₆; X representa un átomo de oxígeno o un grupo -CH₂-, -OCH₂-, -CH₂O-, -CH₂CH₂-, -CH₂NR¹⁷-, -NR¹⁷CH₂-, -CHF- o -CF₂-; m es 0, 1 ó 2; cada R² representa independientemente un átomo de halógeno o un hidroxilo, alquilo C₁₋₆, difluorometilo, trifluorometilo, alcoxi C₁₋₆, difluorometoxi, trifluorometoxi o un grupo NR¹⁵R¹⁶; Y representa CR⁹R¹⁰ en donde R⁹ y R¹⁰ representan cada uno independientemente un átomo de hidrógeno o un grupo metilo; R³ representa, alquilo C₁₋₈, alquenilo C₂₋₈ o un sistema anular de 3 a 10 miembros, saturado o insaturado, que puede comprender al menos un heteroátomo del anillo seleccionado de nitrógeno, oxígeno y azufre, con cada uno de los grupos anteriores opcionalmente sustituido por al menos un sustituyente seleccionado de halógeno, ciano, hidroxilo, cicloalquilo C₃₋₆, alcoxi C₁₋₆, ariloxi C₅₋₆, arilo C₅₋₆alquiloxi C₁₋₆, alcoxicarbonilo C₁₋₆, alcoxicarbonilamino C₁₋₆, alcoxicarboniloxi C₁₋₆, haloalquilo C₁₋₆, haloalcoxi C₁₋₆, -NR¹³R¹⁴, cicloalquilamino C₃₋₆, alquiltio C₁₋₆, alquilcarbonilo C₁₋₆, alquilcarboniloxi C₁₋₆, alquilcarbonilamino C₁₋₆, sulfonamido, alquilsulfonilo C₁₋₆, alquilsulfonilamino C₁₋₆, alquilo C₁₋₆ y un sistema anular de 3 a 10 miembros, saturado o insaturado, que puede comprender al menos un heteroátomo del anillo seleccionado de nitrógeno, oxigeno y azufre, donde el sistema anular en si mismo está opcionalmente sustituido por al menos un sustituyente seleccionado de halógeno, hidroxilo, oxo, carboxilo, ciano, alquilo C₁₋₆, alcoxi C₁₋₆, alcoxicarbonilo C₁₋₆ e hidroxialquilo C₁₋₆; Z representa CR¹¹R¹² en donde R¹¹ y R¹² representan cada uno independientemente un átomo de hidrógeno o un grupo metilo, pero ambos no pueden representar un grupo metilo simultáneamente; n es 0, 1 ó 2; cada R⁴ representa independientemente un átomo de halógeno o un hidroxilo, alquilo C₁₋₆, difluorometilo, trifluorometilo, alcoxi C₁₋₆, difluorometoxi, trifluorometoxi o un grupo NR¹⁸R¹⁹; R⁵ y R⁶ representan cada uno independientemente un átomo de hidrógeno o un grupo alquilo C₁₋₆ o R⁵ y R⁶ junto con el átomo de nitrógeno al cual están unidos forman un heterociclo saturado de 4 a 7 miembros; R⁷ y R⁸ representan cada uno independientemente un átomo de hidrógeno o un grupo alquilo C₁₋₆ o R⁷ y R⁸ junto con el átomo de nitrógeno al cual están unidos forman un heterociclo saturado de 4 a 7 miembros; R¹³ y R¹⁴ representan cada uno independientemente un átomo de hidrógeno o un grupo alquilo C₁₋₆ o R¹³ y R¹⁴ junto con el átomo de nitrógeno al cual están unidos forman un heterociclo saturado de 4 a 7 miembros; R¹⁵ y R¹⁶ representan cada uno independientemente un átomo de hidrógeno o un grupo alquilo C₁₋₆ o R¹⁵ y R¹⁶ junto con el átomo de nitrógeno al cual están unidos forman un heterociclo saturado de 4 a 7 miembros; R¹⁷ representa un átomo de hidrógeno o un grupo alquilo C₁₋₆; R¹⁸ y R¹⁹ representan cada uno independientemente un átomo de hidrógeno o un grupo alquilo C₁₋₆ o R¹⁸ y R¹⁹ junto con el átomo de nitrógeno al cual están unidos forman un heterociclo saturado de 4 a 7 miembros; y los anillos A y B representan cada uno independientemente un sistema anular de 5 a 10 miembros, saturado o insaturado, que puede comprender al menos un heteroátomo del anillo seleccionado de nitrógeno, oxigeno y azufre; o una sal farmacéuticamente aceptable de este.
ARP140103129A 2013-08-20 2014-08-20 Derivados de benzamida como antagonistas de lpar1 y/o lpar5 y un proceso para su preparación AR097403A1 (es)

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KR (1) KR20160045797A (es)
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AU (1) AU2014310404B2 (es)
CA (1) CA2921742A1 (es)
CL (1) CL2016000387A1 (es)
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GB201314926D0 (en) 2013-08-20 2013-10-02 Takeda Pharmaceutical Novel Compounds
JP7173350B2 (ja) 2019-07-30 2022-11-16 大正製薬株式会社 Ｌｐａ１受容体を拮抗するウレア化合物
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TWI838626B (zh) 2020-06-03 2024-04-11 美商基利科學股份有限公司 Lpa受體拮抗劑及其用途
EP4161936A1 (en) 2020-06-03 2023-04-12 Gilead Sciences, Inc. Lpa receptor antagonists and uses thereof
TWI818538B (zh) 2021-05-11 2023-10-11 美商基利科學股份有限公司 Ｌｐａ受體拮抗劑及其用途
CA3238094A1 (en) 2021-12-08 2023-06-15 Gilead Sciences, Inc. Lpa receptor antagonists and uses thereof

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WO2015025164A1 (en) 2015-02-26
US20150057298A1 (en) 2015-02-26
MA38854B1 (fr) 2018-05-31
EA201690390A1 (ru) 2016-08-31
GB201314926D0 (en) 2013-10-02
HK1225712A1 (zh) 2017-09-15
ZA201600753B (en) 2019-07-31
UY35708A (es) 2014-12-31
TN2016000061A1 (en) 2017-07-05
PH12016500322A1 (en) 2016-05-02
KR20160045797A (ko) 2016-04-27
CL2016000387A1 (es) 2016-12-16
EP3036215A1 (en) 2016-06-29
CR20160084A (es) 2016-05-27
AU2014310404A1 (en) 2016-03-10
US20190010129A1 (en) 2019-01-10
TW201536722A (zh) 2015-10-01
JP6422974B2 (ja) 2018-11-14
US9464060B2 (en) 2016-10-11
SG11201601250TA (en) 2016-03-30
EA028818B1 (ru) 2018-01-31
CA2921742A1 (en) 2015-02-26
MX2016001896A (es) 2016-05-26
CN105473548A (zh) 2016-04-06
PE20160284A1 (es) 2016-04-27
JP2016528274A (ja) 2016-09-15
AU2014310404B2 (en) 2018-07-12
CN105473548B (zh) 2018-03-23
US10100018B2 (en) 2018-10-16
MA38854A1 (fr) 2017-07-31
US20160207880A1 (en) 2016-07-21

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