AR091516A1 - Derivados de 1-[m-carboxamido(hetero)aril-metil]-heterociclil-carboxamida - Google Patents

Derivados de 1-[m-carboxamido(hetero)aril-metil]-heterociclil-carboxamida

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Publication number
AR091516A1
AR091516A1 ARP130102184A AR091516A1 AR 091516 A1 AR091516 A1 AR 091516A1 AR P130102184 A ARP130102184 A AR P130102184A AR 091516 A1 AR091516 A1 AR 091516A1
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AR
Argentina
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alkyl
group
substituted
cycloalkyl
mono
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Actelion Pharmaceuticals Ltd
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Publication of AR091516A1 publication Critical patent/AR091516A1/es

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
    • C07D211/66—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4 having a hetero atom as the second substituent in position 4
    • 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
    • C07D401/06—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 linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • 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
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring 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
    • A61K31/435—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
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
    • 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
    • C07D401/12—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 linked by a chain containing hetero atoms as chain links
    • 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
    • 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
    • C07D405/02—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 two hetero rings
    • C07D405/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic 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
    • C07D413/12—Heterocyclic 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
    • 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
    • C07D417/02—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 two hetero rings
    • C07D417/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D471/08—Bridged systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Immunology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Transplantation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pyridine Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pyrrole Compounds (AREA)

Abstract

Reivindicación 1: Un compuesto de la fórmula (1) donde Ar¹ representa un grupo fenileno o un grupo heteroarileno de 5 ó 6 miembros, en donde el grupo -CHR⁴- y el grupo -NH-CO-X-R³ están unidos en una disposición meta a los átomos de carbono del anillo de Ar¹; en donde dicho fenileno o heteroarileno de 5 ó 6 miembros está independientemente insustituido o mono-sustituido, en donde el sustituyente se selecciona a partir del grupo que está seleccionado a partir del grupo que está formado por alquilo C₁₋₄, alcoxi C₁₋₄, halógeno, fluoroalquilo C₁₋₃, y fluoroalcoxi C₁₋₃; (notablemente alquilo C₁₋₄, alcoxi C₁₋₄, y halógeno); X representa un enlace directo (es decir R³ está unido directamente al grupo carbonilo); -alquileno C₁₋₄- que está opcionalmente mono-sustituido, en donde el sustituyente es hidroxi; -cicloalquileno C₃₋₆-; -CH₂-O-, en donde el oxígeno está unido al grupo R³; o -CH=CH-; R³ representa arilo o un heteroarilo de 5 a 10 miembros; en donde dicho arilo o heteroarilo de 5 a 10 miembros está independientemente insustituido, mono-, di- o tri-sustituido, en donde los sustituyentes se seleccionan independientemente a partir del grupo que está formado por alquilo C₁₋₄; alcoxi C₁₋₄; fluoroalquilo C₁₋₃; fluoroalcoxi C₁₋₃; halógeno; ciano; cicloalquilo C₃₋₆; -CO-alcoxi C₁₋₄; -SO₂-alquilo C₁₋₄; y -NR⁶R⁷, en donde R⁶ y R⁷ independientemente representan hidrógeno o alquilo C₁₋₃, o R⁶ y R⁷ junto con el átomo de nitrógeno al cual están unidos forman un anillo de 5 ó 6 miembros seleccionado a partir de pirrolidinilo, morfolinilo, piperidinilo y piperazinilo opcionalmente sustituido en el átomo de nitrógeno vacante con alquilo C₁₋₄; en donde en el caso de que dicho heteroarilo de 5 a 10 miembros sea piridina, dicha piridina puede adicionalmente estar presente en la forma del N-óxido respectivo; o, en caso de que X sea un enlace directo o un grupo metileno, R³ puede además representar un sistema anular bicíclico parcialmente aromático formado por un anillo fenilo que está fusionado a un anillo carboxílico saturado de 4 a 6 miembros que opcionalmente contiene uno o dos heteroátomos independientemente seleccionados a partir de nitrógeno y oxígeno; en donde dicho sistema anular está opcionalmente mono-, o di-sustituido con alquilo C₁₋₄ o halógeno; cicloalquilo C₃₋₈, en donde el cicloalquilo puede opcionalmente contener un átomo de oxígeno anular, y en donde dicho cicloalquilo está opcionalmente sustituido con hasta cuatro grupos metilo; o, en caso de que X sea un enlace directo, R³ puede además representar alquilo C₂₋₆; o, en caso de que X sea -CH=CH-, R³ puede además representar hidrógeno, alquilo C₁₋₄ o (dimetilamino)metilo; R¹ representa alquilo C₁₋₆ que está opcionalmente mono-sustituido con alcoxi C₁₋₄ o hidroxi; fluoroalquilo C₂₋₃; cicloalquilo C₃₋₈ o cicloalquil C₃₋₈-alquilo C₁₋₃; en donde los grupos cicloalquilo C₃₋₈ respectivos pueden opcionalmente contener un átomo de oxígeno anular; en donde el cicloalquilo C₃₋₈ o el cicloalquil C₃₋₈-alquilo C₁₋₃ independientemente está insustituido, o sustituido de la siguiente manera: el grupo cicloalquilo C₃₋₈ está mono- o di-sustituido en donde los sustituyentes están independientemente seleccionado a partir del grupo que está formado por alquilo C₁₋₄, flúor, hidroxi-metilo, hidroxi y ciano; o el grupo alquilo C₁₋₃ está mono-sustituido con hidroxi; aril-alquilo C₁₋₄- o un heteroaril-alquilo C₁₋₄ de 5 ó 6 miembros, en donde el arilo o el heteroarilo de 5 ó 6 miembros independientemente está insustituido, mono- o di-sustituido, en donde los sustituyentes están independientemente seleccionados a partir del grupo que está formado por alquilo C₁₋₄, alcoxi C₁₋₄, halógeno, ciano, fluoroalquilo C₁₋₃, y fluoroalcoxi C₁₋₃ (especialmente alquilo C₁₋₄, alcoxi C₁₋₄, halógeno, y fluoroalquilo C₁₋₃); o un grupo 1,2,3,4-tetrahidronaftalenilo o un grupo indanilo, donde los grupos están unidos al resto de la molécula a través de un átomo de carbono que es parte del anillo no aromático; y R² representa hidrógeno o alquilo C₁₋₃; o R¹ y R² junto con el átomo de nitrógeno al cual están unidos representan un anillo azetidina, pirrolidina, piperidina, morfolina o azepano, en donde dichos anillos están independientemente insustituidos, o mono- o di-sustituidos, en donde los sustituyentes están independientemente seleccionados a partir del grupo que está formado por flúor y metilo; R⁴ representa hidrógeno o alquilo C₁₋₃; y R⁵ᵃ representa hidrógeno, metilo o flúor; R⁵ᵇ representa hidrógeno; y p representa los números enteros 0, 1 ó 2; o R⁵ᵃ representa hidrógeno; R⁵ᵇ representa metilo; y p representa el número entero 1; o una sal farmacéuticamente aceptable del mismo; con la excepción de los compuestos: 1-[1-[3-(benzoilamino)fenil]etil]-N-[(4-fluorofenil)metil]-4-piperidinacarboxamida; y N-[3-[1-[4-(1-pirrolidinilcarbonil)-1-piperidinil]etil]fenil]-benzamida.
ARP130102184 2012-06-22 2013-06-19 Derivados de 1-[m-carboxamido(hetero)aril-metil]-heterociclil-carboxamida AR091516A1 (es)

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US (2) US9428456B2 (es)
EP (1) EP2864315B1 (es)
JP (1) JP6182602B2 (es)
KR (1) KR102101047B1 (es)
CN (1) CN104395302A (es)
AR (1) AR091516A1 (es)
AU (1) AU2013278873B2 (es)
BR (1) BR112014031755A8 (es)
CA (1) CA2875389C (es)
ES (1) ES2768399T3 (es)
MX (1) MX364610B (es)
RU (1) RU2644761C2 (es)
TW (1) TWI623522B (es)
WO (1) WO2013190508A2 (es)

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AR091516A1 (es) 2012-06-22 2015-02-11 Actelion Pharmaceuticals Ltd Derivados de 1-[m-carboxamido(hetero)aril-metil]-heterociclil-carboxamida
PL3004082T3 (pl) * 2013-05-30 2018-01-31 Idorsia Pharmaceuticals Ltd Modulatory receptora cxcr7
UA118034C2 (uk) * 2013-11-14 2018-11-12 Елі Ліллі Енд Компані Заміщений піперидилетилпіримідин як інгібітор грелін-o-ацилтрансферази
EP3227263B1 (en) 2014-12-01 2019-04-10 Idorsia Pharmaceuticals Ltd Cxcr7 receptor modulators
CN109563085B (zh) * 2016-07-28 2022-08-09 爱杜西亚药品有限公司 哌啶cxcr7受体调节剂
EP3609882B1 (en) 2017-03-17 2022-07-13 Cardio Therapeutics Pty Ltd Heterocyclic inhibitors of pcsk9
EP3743422B1 (en) * 2018-01-26 2024-03-13 Idorsia Pharmaceuticals Ltd Crystalline forms of the cxcr7 receptor antagonist (3s,4s)-1-cyclopropylmethyl-4-{[5-(2,4-difluoro-phenyl)-isoxazole-3-carbonyl]-amino}-piperidine-3-carboxylic acid (1-pyrimidin-2-yl-cyclopropyl)-amide
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AR091516A1 (es) 2012-06-22 2015-02-11 Actelion Pharmaceuticals Ltd Derivados de 1-[m-carboxamido(hetero)aril-metil]-heterociclil-carboxamida
PL3004082T3 (pl) 2013-05-30 2018-01-31 Idorsia Pharmaceuticals Ltd Modulatory receptora cxcr7

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JP2015520224A (ja) 2015-07-16
WO2013190508A2 (en) 2013-12-27
MX364610B (es) 2019-05-02
EP2864315A2 (en) 2015-04-29
WO2013190508A3 (en) 2014-03-13
AU2013278873A1 (en) 2015-02-12
CN104395302A (zh) 2015-03-04
EP2864315B1 (en) 2019-11-27
US9428456B2 (en) 2016-08-30
US20150336893A1 (en) 2015-11-26
KR20150023956A (ko) 2015-03-05
KR102101047B1 (ko) 2020-04-16
RU2644761C2 (ru) 2018-02-14
TW201402546A (zh) 2014-01-16
CA2875389A1 (en) 2013-12-27
ES2768399T3 (es) 2020-06-22
BR112014031755A2 (pt) 2017-06-27
US20130345199A1 (en) 2013-12-26
MX2014015691A (es) 2015-08-05
BR112014031755A8 (pt) 2017-12-26
CA2875389C (en) 2020-09-15
JP6182602B2 (ja) 2017-08-16
RU2015101751A (ru) 2016-08-10
TWI623522B (zh) 2018-05-11
AU2013278873B2 (en) 2017-09-28

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