AR093796A1 - Derivados del alcohol 1-fenil-2-piridinil alquilico como inhibidores de la fosfodiesterasa - Google Patents

Derivados del alcohol 1-fenil-2-piridinil alquilico como inhibidores de la fosfodiesterasa

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Publication number
AR093796A1
AR093796A1 ARP130104493A ARP130104493A AR093796A1 AR 093796 A1 AR093796 A1 AR 093796A1 AR P130104493 A ARP130104493 A AR P130104493A AR P130104493 A ARP130104493 A AR P130104493A AR 093796 A1 AR093796 A1 AR 093796A1
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Argentina
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alkyl
optionally substituted
group
heterocycloalkyl
cycloalkyl
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ARP130104493A
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English (en)
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Armani Elisabetta
Capaldi Carmelida
Esposito Oriana
Amari Gabriele
Carzaniga Laura
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Chiesi Farm Spa
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Publication of AR093796A1 publication Critical patent/AR093796A1/es

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    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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    • C07D—HETEROCYCLIC COMPOUNDS
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    • 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
    • C07D213/89—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 with hetero atoms directly attached to the ring nitrogen 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
    • A61K31/33—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
    • A61K31/435—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
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof 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
    • A61K31/495—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
    • 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
    • A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
    • A61M15/00—Inhalators
    • A61M15/0065—Inhalators with dosage or measuring devices
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
    • A61M15/00—Inhalators
    • A61M15/009—Inhalators using medicine packages with incorporated spraying means, e.g. aerosol cans
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
    • A61M16/00—Devices for influencing the respiratory system of patients by gas treatment, e.g. mouth-to-mouth respiration; Tracheal tubes
    • A61M16/10—Preparation of respiratory gases or vapours
    • A61M16/14—Preparation of respiratory gases or vapours by mixing different fluids, one of them being in a liquid phase
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/02—Nasal agents, e.g. decongestants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological 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
    • A61P37/08—Antiallergic agents
    • 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
    • C07D213/61—Halogen atoms or nitro radicals
    • 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
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 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

Abstract

Reivindicación 1: Un compuesto caracterizado porque es de fórmula general (1) donde: R¹ y R² son diferentes o iguales y se seleccionan en forma independiente entre el grupo que consiste en: H; alquilo C₁₋₆ lineal o ramificado, opcionalmente sustituido con uno o más sustituyentes seleccionados entre cicloalquilo C₃₋₇ y cicloalquenilo C₅₋₇; haloalquilo C₁₋₆; cicloalquilo C₃₋₇; cicloalquenilo C₅₋₇; alquenilo C₂₋₆ lineal o ramificado; y alquinilo C₂₋₆ lineal o ramificado; R³ es H o representa uno o más sustituyentes seleccionados en forma independiente entre el grupo que consiste en CN, NO₂, CF₃ y átomos de halógeno; Z es un grupo (CH₂)ₘ donde m = 0 ó 1; A es un anillo fenilo, que está opcionalmente sustituido con uno o más sustituyentes R⁴, que pueden ser iguales o diferentes y se seleccionan en forma independiente entre el grupo que consiste en: alquilo C₁₋₆ lineal o ramificado opcionalmente sustituido con uno o más cicloalquilo C₃₋₇ o heterocicloalquilo C₃₋₇; haloalquilo C₁₋₆; alquiltio C₁₋₆; halógeno; NH₂; y OR⁷ donde R⁷ se selecciona entre el grupo que consiste en H; alquilo C₁₋₁₀ opcionalmente sustituido con un radical seleccionado entre cicloalquilo C₃₋₇, heterocicloalquilo C₃₋₇, arilo y heteroarilo; alquilo C₁₋₁₀ sustituido con un grupo OH; haloalquilo C₁₋₆; cicloalquilo C₃₋₇; alquil C₁₋₄aminocarbonilo; alquil C₁₋₄oxicarbonilo; heterocicloalquilo C₃₋₇ opcionalmente sustituido con alquilo C₁₋₄; y R⁵R⁶N-alquileno C₁₋₁₀ donde R⁵ y R⁶ se seleccionan en forma independiente entre el grupo que consiste en H, alquilo C₁₋₆ lineal o ramificado o, con el átomo de nitrógeno al cual están unidos, forman un anillo saturado, parcialmente saturado o insaturado, donde estos anillos están opcionalmente sustituidos con alquilo C₁₋₄, átomos de halógeno o R⁷R⁸N-alquileno C₁₋₄ donde R⁷ y R⁸ son diferentes o iguales y se seleccionan en forma independiente entre el grupo que consiste en H, alquilo C₁₋₆ lineal o ramificado o, con el átomo de nitrógeno al cual están unidos, forman un anillo saturado o parcialmente saturado; W se selecciona entre el grupo que consiste en: -NR⁹SO₂R¹⁰ donde R⁹ se selecciona entre el grupo que consiste en alquilo C₁₋₁₀ opcionalmente sustituido con cicloalquilo C₃₋₇, heterocicloalquilo C₃₋₇, heterocicloalquil C₃₋₇carbonilo, donde cualquiera de dichos anillos puede estar opcionalmente sustituido con uno o más alquilo C₁₋₄ o OH; y R¹¹R¹²N-alquileno C₁₋₁₀ donde R¹¹ y R¹² son en forma independiente H o alquilo C₁₋₆, cada uno de los cuales puede estar opcionalmente sustituido con un grupo OH; y R¹⁰ se selecciona entre el grupo que consiste en alquilo C₁₋₄ opcionalmente sustituido con cicloalquilo C₃₋₇; cicloalquilo C₃₋₇; y fenilo, cualquiera de los cuales puede estar opcionalmente sustituido con uno o más átomos de halógeno o grupos alquilo C₁₋₄; -CH₂NR¹³SO₂R¹⁴ donde R¹³ se selecciona entre el grupo que consiste en: H; cicloalquilo C₃₋₇; alquilo C₁₋₁₀ opcionalmente sustituido con cicloalquilo C₃₋₇, heterocicloalquilo C₃₋₇, donde cualquiera de dichos anillos puede estar opcionalmente sustituido con alquilo C₁₋₄; y R¹¹R¹²N-alquileno C₁₋₁₀ donde R¹¹ y R¹² son en forma independiente H o alquilo C₁₋₆, cada uno de los cuales puede estar opcionalmente sustituido con un grupo OH; R¹⁴ se selecciona entre el grupo que consiste en: alquilo C₁₋₄; heterocicloalquil C₃₋₇-alquileno C₁₋₄; fenilo, cualquiera de los cuales puede estar opcionalmente sustituido con uno o más átomos de halógeno o grupos alquilo C₁₋₄; -alquilen C₁₋₄-heterocicloalquilo C₃₋₇, que puede estar opcionalmente sustituido con uno o más grupos seleccionados entre: oxo, OH, SH, alquilo C₁₋₄ e hidroxi-alquileno C₁₋₆; anillo -heterocicloalquilo C₃₋₇, que puede estar opcionalmente sustituido con uno o más grupos seleccionados entre: oxo, OH, SH, alquilo C₁₋₄ e hidroxi-alquileno C₁₋₆; -alquilen C₁₋₄-amino-heterocicloalquilo C₃₋₇, que puede estar opcionalmente sustituido con uno o más grupos seleccionados entre: oxo, OH, SH, alquilo C₁₋₄ e hidroxi-alquileno C₁₋₆; -SO₂NR¹⁵R¹⁶ donde R¹⁵ se selecciona entre el grupo que consiste en H y alquilo C₁₋₁₀; y R¹⁶ se selecciona entre el grupo que consiste en: alquilo C₁₋₁₀ el cual está opcionalmente sustituido con cicloalquilo C₃₋₇ o heterocicloalquilo C₃₋₇, donde cualquiera de dichos anillos puede estar opcionalmente sustituido con alquilo C₁₋₄; y R¹¹R¹²N-alquileno C₁₋₁₀ donde R¹¹ y R¹² son en forma independiente H o alquilo C₁₋₆, cada uno de los cuales puede estar opcionalmente sustituido con un grupo OH; o R¹⁵ y R¹⁶, junto con el átomo de nitrógeno al cual están unidos, forman un anillo heterocicloalquilo C₃₋₇ opcionalmente sustituido con uno o más alquilo C₁₋₄; -NHSO₂R¹⁷ donde R¹⁷ se selecciona entre el grupo que consiste en: alquilo C₁₋₁₀ el cual está opcionalmente sustituido con cicloalquilo C₃₋₇, heterocicloalquilo C₃₋₇, arilo y heteroarilo, donde cualquiera de dichos anillos puede estar opcionalmente sustituido con alquilo C₁₋₄; R¹¹R¹²N-alquileno C₁₋₁₀ donde R¹¹ y R¹² son en forma independiente H o alquilo C₁₋₆, cada uno de los cuales puede estar opcionalmente sustituido con un grupo OH; -OSO₂R¹⁸ donde R¹⁸ se selecciona entre el grupo que consiste en: alquilo C₁₋₁₀ el cual está opcionalmente sustituido con halógeno, OH, alcoxilo C₁₋₄, cicloalquilo C₃₋₇, heterocicloalquilo C₃₋₇, arilo o heteroarilo, donde cualquiera de dichos anillos puede estar opcionalmente sustituido con alquilo C₁₋₄; y R¹¹R¹²N-alquileno C₁₋₁₀ donde R¹¹ y R¹² son en forma independiente H o alquilo C₁₋₆, cada uno de los cuales puede estar opcionalmente sustituido con un grupo OH; -OC(O)R¹⁹ donde R¹⁹ se selecciona entre el grupo que consiste en: cicloalquilo C₃₋₇, heterocicloalquilo C₃₋₇, donde cualquiera de dichos anillos puede estar opcionalmente sustituido con alquilo C₁₋₄; alquilo C₁₋₁₀ el cual está opcionalmente sustituido con uno o más halógeno, OH, NH₂, cicloalquilo C₃₋₇, heterocicloalquilo C₃₋₇, donde cualquiera de dichos anillos puede estar opcionalmente sustituido con alquilo C₁₋₄; y R¹¹R¹²N-alquileno C₁₋₁₀ donde R¹¹ y R¹² son en forma independiente H o alquilo C₁₋₆, cada uno de los cuales puede estar opcionalmente sustituido con un grupo OH; -C(O)R²⁰ donde R²⁰ se selecciona entre el grupo que consiste en: -NR²¹R²² donde R²¹ y R²² se seleccionan en forma independiente entre: H, alquilo C₁₋₆, cicloalquilo C₃₋₇ y heterocicloalquil C₃₋₇-alquileno C₁₋₄, cada uno de los cuales puede estar opcionalmente sustituido con alquilo C₁₋₄, OH, NH₂ o, con el átomo de nitrógeno al cual están unidos, forman un anillo heterocíclico saturado o parcialmente saturado que puede estar opcionalmente sustituido con alquilo C₁₋₄, OH o NH₂; -OR²³ donde R²³ es alquilo C₁₋₁₀ el cual está sustituido con uno o más halógeno, OH, cicloalquilo C₃₋₇, heterocicloalquilo C₃₋₇, donde cualquiera de dichos anillos puede estar opcionalmente sustituido con alquilo C₁₋₄; -NH-alquilen C₁₋₄-NR²⁴R²⁵ donde R²⁴ y R²⁵, iguales o diferentes, se seleccionan en forma independiente entre H y alquilo C₁₋₆ o, con el átomo de nitrógeno al cual están unidos, forman un anillo saturado o parcialmente saturado, que está opcionalmente sustituido con uno o más grupos alquilo C₁₋₄; -NHCOR²⁶ donde R²⁶ se selecciona entre el grupo que consiste en: R²⁷R²⁸N-alquileno C₁₋₆ donde R²⁷ y R²⁸, iguales o diferentes, se seleccionan
ARP130104493A 2012-12-05 2013-12-04 Derivados del alcohol 1-fenil-2-piridinil alquilico como inhibidores de la fosfodiesterasa AR093796A1 (es)

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US (1) US9944612B2 (es)
EP (1) EP2928869B1 (es)
KR (1) KR102192739B1 (es)
CN (2) CN104822659A (es)
AR (1) AR093796A1 (es)
BR (1) BR112015012724A2 (es)
CA (1) CA2893628C (es)
ES (1) ES2716142T3 (es)
HK (1) HK1213551A1 (es)
PL (1) PL2928869T3 (es)
RU (1) RU2655170C2 (es)
TR (1) TR201907092T4 (es)
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EP3060551B1 (en) 2013-10-22 2019-09-18 Chiesi Farmaceutici S.p.A. Process for the preparation of a pde4 inhibitor
AR104822A1 (es) * 2015-06-01 2017-08-16 Chiesi Farm Spa Derivado de aminoésteres
TW201710254A (zh) * 2015-06-01 2017-03-16 吉斯藥品公司 胺基酯衍生物
EP3732164A1 (en) * 2017-12-28 2020-11-04 Chiesi Farmaceutici S.p.A. Use of 1-phenyl-2-pyridinyl alkyl alcohol derivatives for treating cystic fibrosis

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RU2015121045A (ru) 2017-01-11
US9944612B2 (en) 2018-04-17
CN104822659A (zh) 2015-08-05
KR102192739B1 (ko) 2020-12-18
CN110698459B (zh) 2023-05-05
BR112015012724A2 (pt) 2017-07-11
RU2655170C2 (ru) 2018-05-24
EP2928869B1 (en) 2019-02-20
US20140155391A1 (en) 2014-06-05
KR20150092214A (ko) 2015-08-12
TWI628166B (zh) 2018-07-01
CA2893628A1 (en) 2014-06-12
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