AR091930A1 - Agentes moduladores de autotaxina (atx) - Google Patents

Agentes moduladores de autotaxina (atx)

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Publication number
AR091930A1
AR091930A1 ARP130102688A ARP130102688A AR091930A1 AR 091930 A1 AR091930 A1 AR 091930A1 AR P130102688 A ARP130102688 A AR P130102688A AR P130102688 A ARP130102688 A AR P130102688A AR 091930 A1 AR091930 A1 AR 091930A1
Authority
AR
Argentina
Prior art keywords
alkyl
carbamoyl
sulfamoyl
independently selected
heteroaryl
Prior art date
Application number
ARP130102688A
Other languages
English (en)
Original Assignee
Biogen Idec Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=49997862&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=AR091930(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Biogen Idec Inc filed Critical Biogen Idec Inc
Publication of AR091930A1 publication Critical patent/AR091930A1/es

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
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    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • A61K31/136—Amines having aromatic rings, e.g. ketamine, nortriptyline having the amino group directly attached to the aromatic ring, e.g. benzeneamine
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    • 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
    • A61K31/196—Carboxylic acids, e.g. valproic acid having an amino group the amino group being directly attached to a ring, e.g. anthranilic acid, mefenamic acid, diclofenac, chlorambucil
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    • 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
    • A61K31/439—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 the ring forming part of a bridged ring system, e.g. quinuclidine
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    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
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    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
    • C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
    • C07C217/18—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
    • C07C217/22—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted by carbon atoms having at least two bonds to oxygen atoms
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    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/46—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
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    • C07C229/46—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C229/48—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups and carboxyl groups bound to carbon atoms of the same non-condensed ring
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    • C07C229/46—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C229/50—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups and carboxyl groups bound to carbon atoms being part of the same condensed ring system
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    • 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
    • C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
    • C07C255/59—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
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    • 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
    • C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/34—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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Abstract

Compuestos con propiedades terapéuticas para enfermedades inflamatorias y autoinmunes. Reivindicación 1: Un compuesto caracterizado representado por la fórmula (1) o una sal del mismo farmacéuticamente aceptable, en donde X puede ser O, S(O)ʳ, NR¹², C(O) o CH₂; A¹ y A² pueden cada uno ser independientemente CR² o N; A³, A⁴ y A⁵ pueden cada uno ser independientemente CR², C(R²)₂, N, o NR¹⁹, siempre que al menos tres de A¹, A², A³, A⁴, A⁵, y A⁶ son independientemente CR² o C(R²)₂; - - - - - indica un enlace único o doble; R¹ puede ser un alquilo C₆₋₂₀, un carbociclilo C₃₋₁₄, un heterociclilo de 3 a 15 elementos, un arilo C₆₋₁₀, o un heteroarilo de 5 a 14 elementos, en donde el heterociclilo y el heteroarilo comprenden de 1 a 10 heteroátomos seleccionados independientemente de N, S, u O, y en donde R¹ puede ser opcionalmente sustituido a partir de uno a seis R⁶ independientemente seleccionados; R², para cada aparición, puede ser independientemente seleccionado a partir del grupo que consiste de hidrógeno, halo, hidroxilo, nitro, ciano, carboxi, alquilo C₁₋₆, haloalquilo C₁₋₆, cicloalquilo C₃₋₈, halocicloalquilo C₃₋₈, alcoxi C₁₋₆, haloalcoxi C₁₋₆, cicloalcoxi C₃₋₈, halocicloalcoxi C₃₋₈, alcanoilo C₁₋₆, amino, N-(alquilo C₁₋₆)amino, N,N-di-(alquilo C₁₋₆)amino, alcoxicarbonilo C₁₋₆, alcanoiloxi C₁₋₆, carbamoilo, N-(alquilo C₁₋₆)carbamoilo, N,N-di-(alquilo C₁₋₆)carbamoilo, alquilamido C₁₋₆, mercapto, alquiltio C₁₋₆, alquilsulfonilo C₁₋₆, sulfamoilo, N-(alquilo C₁₋₆)sulfamoilo, N,N-di-(alquilo C₁₋₆)sulfamoilo, y alquilsulfonamido C₁₋₆; R³ puede ser hidrógeno, un halo, haloalquilo C₁₋₆ o ciano, siempre que cuando R³ es hidrógeno, R¹ es un cicloalquilo C₃₋₈ el cual es opcionalmente sustituido de 1 a 6; R⁴ es un ácido carboxílico o un grupo representado por la fórmula (2) en donde la línea ondulada representa el punto de unión; siempre que cuando R⁴ es un ácido carboxílico, A¹ es N y R¹ es un cicloalquilo C₃₋₈ el cual es opcionalmente sustituido de 1 a 6; R⁵ puede ser un alquileno C₁₋₆, carbociclilo C₃₋₈, un heterociclilo de 3- a 8-elementos, arilo C₆₋₁₀, un heteroarilo de 5- a 10-elementos, un sistema de anillo puenteado que comprende de 6 a 12 elementos en el anillo, un sistema de anillo espiro que comprende de 5-14 elementos en el anillo, o un sistema de anillo bicíclico representado por la fórmula (3) en donde B y B son independientemente seleccionados del grupo que consiste de carbociclilo C₃₋₈ monocíclico, un heterociclilo monocíclico de 3- a 8-elementos, fenilo o un heteroarilo de 5- a 6-elementos; en donde R⁵ puede ser opcionalmente sustituido a partir de 1 a 4 R¹¹ independientemente seleccionados; R⁶, para cada aparición, puede ser independientemente seleccionado a partir del grupo que consiste de halo, alquilo C₁₋₆, alcoxi C₁₋₆, haloalquilo C₁₋₆, cicloalquilo C₃₋₈, arilo C₆₋₁₀, alcoxi C₁₋₆-alquilo C₁₋₆, y tri- (alquilo C₁₋₆)sililo; o dos R⁶ que están unidos al mismo átomo de carbono pueden formar espirocicloalquilo C₃₋₈ o espiroheterocicloalquilo de 3- a 8-elementos; R⁷ puede ser -OH, -C(O)OR¹⁵, -C(O)N(R¹⁶)₂, -C(O)N(R¹⁵)-S(O)₂R¹⁵, -S(O)₂OR¹⁵, -C(O)NHC(O)R¹⁵, -Si(O)OH, -B(OH)₂, -N(R¹⁵)S(O)₂R¹⁵, -S(O)₂N(R¹⁵)₂, -O-P(O)(OR¹⁵)₂, -P(O)(OR¹⁵)₂, -CN, -S(O)₂NHC(O)R¹⁵, -C(O)NHS(O)₂R¹⁵, -C(O)NHOH, -C(O)NHCN, o un heteroarilo o un heterociclilo seleccionados del grupo de fórmulas (4); R⁸ y R⁹ pueden cada uno ser independientemente hidrógeno, un carboxi, alquilo C₁₋₆, o un alquenilo C₂₋₆; o R⁸ y R⁹ junto con el carbono al cual están unidos pueden ser -C(=O)-, un espirocicloalquilo C₃₋₈, o un espiroheterocicloalquilo de 3- a 8-elementos; R¹⁰ y R¹² pueden cada uno ser independientemente hidrógeno o un alquilo C₁₋₆; R¹¹, para cada aparición, puede ser independientemente halo, hidroxilo, nitro, ciano, alquilo C₁₋₆, haloalquilo C₁₋₆, alcoxi C₁₋₆, -(CR¹⁷R¹⁸)ₚ-R⁷, haloalcoxi C₁₋₄, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₈, halocicloalquilo C₃₋₈, cicloalcoxi C₃₋₈, halocicloalcoxi C₃₋₈, -NRᵃRᵇ, -C(O)NRᵃRᵇ, -N(Rᵃ)C(O)Rᵇ, -C(O)Rᵃ, -S(O)ʳRᵃ, o -N(Rᵃ)S(O)₂Rᵇ; R¹⁵ para cada aparición puede ser independientemente seleccionado a partir del grupo que consiste de hidrógeno, alquilo C₁₋₈, alquenilo C₂₋₈, alquinilo C₂₋₈, cicloalquilo C₃₋₈, cicloalquenilo C₃₋₈, arilo C₆₋₁₀, un heteroarilo de 5 a 14 elementos, y un heterociclilo de 3 a 15 elementos; en donde el heteroarilo o heterociclilo comprende de 1 a 10 heteroátomos seleccionados independientemente de O, N, o S; y en donde R¹⁵ puede ser opcionalmente sustituido a partir de 1 a 3 sustituyentes independientemente seleccionados del grupo que consiste de halo, alcoxi C₁₋₄, alquilo C₁₋₄, ciano, nitro, hidroxilo, amino, N-(alquilo C₁₋₄)amino, N,N-di-(alquilo C₁₋₄)amino, carbamoilo, N-(alquilo C₁₋₄)carbamoilo, N,N-di-(alquilo C₁₋₄)carbamoilo, alquilamido C₁₋₄, alquilsulfonilo C₁₋₄, alquilsulfonamido C₁₋₄, sulfamoilo, N-(alquilo C₁₋₄)sulfamoilo, y N,N-(dialquilo C₁₋₄)-sulfamoilo; R¹⁶ puede ser R¹⁵ o dos R¹⁶ junto con el átomo de nitrógeno al cual están unidos pueden formar un heteroarilo de 5 a 14 elementos o un heterociclilo de 3 a 15 elementos, en donde el heteroarilo o heterociclilo comprende de 1 a 10 heteroátomos seleccionados independientemente de O, N, o S; y en donde el heteroarilo o heterociclilo pueden ser opcionalmente sustituidos a partir de 1 a 3 sustituyentes independientemente seleccionados del grupo que consiste de halo, alcoxi C₁₋₄, alquilo C₁₋₄, ciano, nitro, hidroxilo, amino, N-(alquilo C₁₋₄)amino, N,N-di-(alquilo C₁₋₄)amino, carbamoilo, N-(alquilo C₁₋₄)carbamoilo, N,N-di-(alquilo C₁₋₄)carbamoilo, alquilamido C₁₋₄, alquilsulfonilo C₁₋₄, alquilsulfonamido C₁₋₄, sulfamoilo, N-alquilsulfamoilo C₁₋₄, y N,N-(dialquilo C₁₋₄)-sulfamoilo; R¹⁷ y R¹⁸, para cada aparición, puede ser cada uno independientemente hidrógeno, un halo, o un haloalquilo C₁₋₄; R¹⁹ para cada aparición puede ser independientemente seleccionado a partir del grupo que consiste de hidrógeno, carboxi, alquilo C₁₋₆, haloalquilo C₁₋₆, cicloalquilo C₃₋₈, halocicloalquilo C₃₋₈, alcanoilo C₁₋₆, alcoxicarbonilo C₁₋₆, carbamoilo, N-(alquilo C₁₋₆)carbamoilo, N,N-di-(alquilo C₁₋₆)carbamoilo, alquilsulfonilo C₁₋₆, sulfamoilo, N-(alquilo C₁₋₆)sulfamoilo, y N,N-di-(alquilo C₁₋₆)sulfamoilo; Rᵃ y Rᵇ, para cada aparición, puede ser independientemente hidrógeno, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₈, arilo C₆₋₁₀, o halocicloalquilo C₃₋₈; Rᶜ es hidrógeno o un alquilo C₁₋₄; m puede ser 0 ó 1, siempre que cuando m es 0, R⁵ comprende al menos un nitrógeno; n puede ser un número entero de 1 a 6; p puede ser 0 o un numero entero de 1 a 6; r, para cada aparición, puede ser independientemente 0, 1, ó 2, siempre que el compuesto no es ácido 4,4-((perfluoronaftaleno-2,7-diil)bis(metilen))dipiridina, 3-(1,4-dioxaespiro[4.5]decan-8-ilamino)-8-metilisoquinolin-6-carboxílico, o (2-metoxi-3-(morfolinometil)quinolin-6-il) (4-metoxiciclohexil)metanona.
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