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AR086676A1 - Derivados de alcoholes 1-fenil-2-piridinil alquilicos como inhibidores de fosfodiesterasa - Google Patents

Derivados de alcoholes 1-fenil-2-piridinil alquilicos como inhibidores de fosfodiesterasa

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Publication number
AR086676A1
AR086676A1 ARP120101983A ARP120101983A AR086676A1 AR 086676 A1 AR086676 A1 AR 086676A1 AR P120101983 A ARP120101983 A AR P120101983A AR P120101983 A ARP120101983 A AR P120101983A AR 086676 A1 AR086676 A1 AR 086676A1
Authority
AR
Argentina
Prior art keywords
group
alkyl
optionally substituted
cycloalkyl
heterocycloalkyl
Prior art date
Application number
ARP120101983A
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English (en)
Inventor
Elisabetta Armani
Gabriele Amari
Laura Carzaniga
Carmelida Capaldi
Oriana Esposito
Gino Villetti
Fanti Renato De
Original Assignee
Chiesi Farma Spa
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Application filed by Chiesi Farma Spa filed Critical Chiesi Farma Spa
Publication of AR086676A1 publication Critical patent/AR086676A1/es

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    • 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
    • A61K31/4425—Pyridinium derivatives, e.g. pralidoxime, pyridostigmine
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    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
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    • 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
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    • 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 or sparfloxacin
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    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
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    • 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
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    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/538—1,4-Oxazines, e.g. morpholine ortho- or peri-condensed with carbocyclic ring systems
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    • A61K31/54—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 sulfur as the ring hetero atoms, e.g. sulthiame
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    • A61K31/63—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide
    • A61K31/635—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide having a heterocyclic ring, e.g. sulfadiazine
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    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
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    • 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
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    • 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
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Abstract

Composiciones farmacéuticas, proceso para preparar los compuestos, uso terapéutico para enfermedades del tracto respiratorio, dispositivo.Reivindicación 1: Un compuesto caracterizado porque es de fórmula general [1] donde: R1 se selecciona entre el grupo que consiste en: H; cicloalquil C3-7carbonilo; alquilo C1-6, opcionalmente sustituido con uno o más sustituyentes seleccionados entre cicloalquilo C3-7 o cicloalquenilo C5-7; haloalquilo C1-6; cicloalquilo C3-7; cicloalquenilo C5-7; alquenilo C2-6; y alquinilo C2-6; R2 se selecciona entre el grupo que consiste en: H; cicloalquil C3-7carbonilo; alquilo C1-6, opcionalmente sustituido con uno o más sustituyentes seleccionados entre cicloalquilo C3-7 o cicloalquenilo C5-7; haloalquilo C1-6; cicloalquilo C3-7; cicloalquenilo C5-7; alquenilo C2-6; y alquinilo C2-6; o, cuando R19 es distinto de hidrógeno, R2 forma junto con R19 un grupo de fórmula [2] como se define más adelante; o R1 y R2, junto con los átomos que los conectan, forman un anillo 2,2-difluoro-1,3-dioxolano de fórmula [3] fusionado a la porción fenilo que lleva los grupos -OR1 y -OR2, donde los asteriscos indican átomos de carbono compartidos con dicho anillo fenilo; R19 es hidrógeno o, de ser distinto de hidrógeno, forma junto con R2 un grupo de fórmula [2] donde los enlaces marcados con (1) y (2) indican los puntos de unión del grupo de fórmula [2] a los átomos que llevan los grupos R19 y R2 respectivamente, de manera que R2 y R19 junto con los átomos que los conectan forman un anillo de fórmula [4] que está fusionado a un anillo fenilo que lleva los grupos -OR2 y R19, donde los asteriscos indican átomos de carbono compartidos con dicho anillo fenilo; R3 es uno o más sustituyentes seleccionados en forma independiente entre el grupo que consiste en H, CN, NO2, CF3 y átomos de halógeno; Z es un grupo -(CH2)n- donde n es 0 ó 1; A es un heterocicloalquileno C3-7 monocíclico saturado; K se selecciona entre el grupo que consiste en: -(CH2)mC(O)R4 donde m puede ser 0 ó 1; -C(O)(CH2)jR4 donde j puede ser 1 ó 2; -SO2(CH2)pR4 donde p puede ser cero, 1 ó 2; -(CH2)ySO2R4 donde y puede ser 1 ó 2; -(CH2)zR4 donde z puede ser 1 ó 2; y -C(O)(CH2)2SO2R4; R4 es un sistema de anillos, que es un anillo monocíclico o bicíclico que puede ser saturado, parcialmente insaturado o totalmente insaturado, como por ejemplo arilo, cicloalquilo C3-8, heterocicloalquilo C3- o heteroarilo, donde el anillo está opcionalmente sustituido con uno o más grupos R5 que pueden ser iguales o diferentes, y que se seleccionan en forma independiente entre el grupo que consiste en: alquilo C1-6 opcionalmente sustituido con uno o más grupos seleccionados en forma independiente de la lista que consiste en: cicloalquilo C3-7, -OH y un grupo -NR18C(O)alquilo C1-4, donde R18 es hidrógeno o alquilo C1-4; heterocicloalquilo C3-7; heteroarilo de 5 ó 6 miembros el cual está opcionalmente sustituido con uno o dos grupos alquilo C1-4; haloalquilo C1-6; heterocicloalquil C3-7alquilo C1-4; - un grupo -OR6 donde R6 se selecciona entre el grupo que consiste en H; haloalquilo C1-6; un grupo -SO2R7, donde R7es alquilo C1-4; un grupo -C(O)R7 donde R7 es alquilo C1-4; alquilo C1-10 opcionalmente sustituido con uno o más cicloalquilo C3-7 o con un grupo -NR8R9 como se define más adelante; y cicloalquilo C3-7; un grupo -SR20 donde R20 se selecciona entre el grupo que consiste en H; haloalquilo C1-6; - un grupo -C(O)R7 donde R7 es alquilo C1-4; alquilo C1-10 opcionalmente sustituido con uno o más cicloalquilo C3-7 o con un grupo -NR8R9; y cicloalquilo C3-7; átomos de halógeno; CN; - NO2; NR8R9 donde R8 y R9 son iguales o diferentes y se seleccionan en forma independiente entre el grupo que consiste en: H; alquilen C1-4-NR13R14 donde R13 y R14 son iguales o diferentes y se seleccionan en forma independiente entre el grupo que consiste en: H y alquilo C1-6, que está opcionalmente sustituido con cicloalquilo C3-7 o heterocicloalquilo C3-7; o forman con el átomo de nitrógeno al cual están unidos un anillo heterocíclico C3-7 saturado o parcialmente saturado; alquilo C1-6, opcionalmente sustituido con cicloalquilo C3-7, heterocicloalquilo C3-7, un grupo -OH o alcoxilo C1-6; un grupo -SO2R15, donde R15 se selecciona entre el grupo que consiste en: alquilo C1-4 opcionalmente sustituido con cicloalquilo C3-7 o heterocicloalquilo C3-7; heterocicloalquilo C3-7; y fenilo opcionalmente sustituido con uno o más alquilo C1-6, halógeno o un grupo -OH; un grupo -C(O)R16, donde R16 se selecciona entre el grupo que consiste en: alquilo C1-6 opcionalmente sustituido con cicloalquilo C3-7 o heterocicloalquilo C3-7; heterocicloalquilo C3-7; fenilo opcionalmente sustituido con uno o más alquilo C1-6, halógeno o -OH; y un grupo -NH2; un grupo -C(O)OR17, donde R17 se selecciona entre el grupo que consiste en: alquilo C1-6 opcionalmente sustituido con cicloalquilo C3-7 o heterocicloalquilo C3-7; heterocicloalquilo C3-7; fenilo opcionalmente sustituido con uno o más alquilo C1-6, halógeno o -OH; y un grupo -NH2; o forman con el átomo de nitrógeno al cual están unidos un anillo heterocíclico saturado o parcialmente saturado, que está opcionalmente sustituido con uno o más alquilo C1-6 o grupos oxo; alquilen C1-4-NR8R9 como se ha definido; COR10 donde R10 es fenilo o alquilo C1-6; oxo; -SO2R11 donde R11 es alquilo C1-4, OH o NR8R9 donde R8 y R9 son como se definen precedentemente; -COOR12 donde R12 es H, alquilo C1-4 o alquilen C1-4-NR8R9 donde R8 y R9 son como se definen precedentemente; y -CONR8R9 donde R8 y R9 son como se definen precedentemente; donde los grupos R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19 y R20 pueden tener significados iguales o diferentes en cada caso, si se encuentran presentes en más que un grupo; derivados N-óxido sobre el anillo piridina, o sales farmacéuticamente aceptables, o solvatos del mismo.
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