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AR055271A1 - COMPOSITE OF CARBOXYLIC BIFENIL ACID, PHARMACEUTICAL COMPOSITION THAT INCLUDES IT, ITS USE TO PREPARE THIS LAST AND PROCESS TO PREPARE IT - Google Patents

COMPOSITE OF CARBOXYLIC BIFENIL ACID, PHARMACEUTICAL COMPOSITION THAT INCLUDES IT, ITS USE TO PREPARE THIS LAST AND PROCESS TO PREPARE IT

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Publication number
AR055271A1
AR055271A1 ARP050104182A ARP050104182A AR055271A1 AR 055271 A1 AR055271 A1 AR 055271A1 AR P050104182 A ARP050104182 A AR P050104182A AR P050104182 A ARP050104182 A AR P050104182A AR 055271 A1 AR055271 A1 AR 055271A1
Authority
AR
Argentina
Prior art keywords
alkyl
optionally substituted
hydrogen
independently
groups
Prior art date
Application number
ARP050104182A
Other languages
Spanish (es)
Original Assignee
Smithkline Beecham Corp
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
Application filed by Smithkline Beecham Corp filed Critical Smithkline Beecham Corp
Publication of AR055271A1 publication Critical patent/AR055271A1/en

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    • C07C233/64Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/65Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
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    • C07C233/63Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
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    • C07C233/67Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/68Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/69Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of an acyclic saturated carbon skeleton
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    • C07C233/77Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/78Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
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    • C07D213/04Heterocyclic 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
    • C07D213/60Heterocyclic 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
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Abstract

Compuestos del ácido bifenil carboxílico de la formula (1), en la que R1 se selecciona entre hidrogeno; alquilo C1-6 opcionalmente sustituido con hasta tres grupos seleccionados independientemente entre alcoxi C1-6, halogeno e hidroxi; cicloalquilo C3-7 opcionalmente sustituido independientemente con uno o más grupos de alquilo C1-6; un anillo arilo, heteroarilo, o heterociclilo cada uno opcionalmente sustituido, independientemente, con uno a tres grupos seleccionados entre R5 y R6; R2 es hidrogeno, alquilo C1-6 o un -(CH2)p-cicloalquiloC3-7 opcionalmente sustituido independientemente con uno o más grupos alquilo C1-6, o (CH2)mR1 y R2, junto con el átomo de nitrogeno al que están unidos, forman un anillo heterocíclico de cuatro a seis miembros opcionalmente sustituido, que contiene opcionalmente otro heteroátomo seleccionado entre O/N/S; R3 es halogeno o metilo; R4 es hidrogeno, alquilo C1-6, alquilo C1-6, halo-alquiloC1-4 sustituido o cicloalquilo C3-7; R5 es independientemente alquilo C1-6, OR4, -(CH2)p-cicloalquiloC3-7 opcionalmente sustituido independientemente con uno o más grupos alquilo C1-6, -CONR9R10, -NHCOR10, -SO2NHR9, -(CH2)qNHSO2R10, halogeno, CN, -(CH2)qNR11R12, y trifluorometilo; R6 es independientemente hidrogeno, alquilo C1-6, OR4, halogeno, trifluorometilo y -(CH2)qNR11R12; R8 se selecciona entre hidrogeno, alquilo C1-6, cicloalquilo C3-7 opcionalmente sustituido con uno o más grupos alquilo C1-6, OH, alquilo C1-6 opcionalmente sustituido con uno o más grupos hidroxilo, CONHR9, fenilo opcionalmente sustituido con R13 y/o R14, o un heteroarilo opcionalmente sustituido con R13 y/o R14; cada uno de R9 y R10 se selecciona independientemente entre hidrogeno y alquilo C1-6, o R9 y R10, junto con el átomo de nitrogeno al que están unidos, forman un anillo heterocíclico de cinco a seis miembros que opcionalmente contiene un heteroátomo adicional seleccionado entre oxígeno, azufre y N-R15, donde el anillo está opcionalmente sustituido con hasta dos grupos alquilo C1-6; R11 se selecciona entre hidrogeno, alquilo C1-6 y -(CH2)p-cicloalquiloC3-7 opcionalmente sustituido con uno o más grupos alquilo C1-6; R12 se selecciona entre hidrogeno y alquilo C1-6, o R11 y R12, junto con el átomo de nitrogeno al que están unidos, forman un anillo heterocíclico de cinco o seis miembros que opcionalmente contiene un heteroátomo adicional seleccionado entre oxígeno, azufre y N-R15; R13 se selecciona entre alquilo C1-6, alcoxi C1-6, -(CH2)p-cicloalquiloC3-7 opcionalmente sustituido con uno o más grupos alquilo C1-6, -CONR9R10, -NHCOR10, halogeno, CN, -(CH2)qNR11R12, trifluorometilo, fenilo opcionalmente sustituido independientemente con uno o más grupos R14, heterociclilo opcionalmente sustituido independientemente con uno o más grupos R14, y un heteroarilo opcionalmente sustituido independientemente con uno o más grupos R14; R14 se selecciona entre alquilo C1-6, alcoxi C1-6, halogeno, halo-alquiloC1-4 sustituido y NR11R12; R15 se selecciona entre hidrogeno y metilo; cada uno de X e Y se selecciona independientemente entre hidrogeno, metilo y halogeno; Z se selecciona entre -(CH2)sCOOR16, o -(CH2)sCONR16R17; R16 y R17 se seleccionan independientemente entre hidrogeno, alquilo C1-6 opcionalmente sustituido, -(CR20R21)vOR18, -(CR20R2I)vNR18R19, -(CR20R21)vNHSO2R18, -(CR20R21)vCONR18R19, -(CR20R21)vCOOR18, -(CR20R21)theteroarilo opcionalmente sustituido, -(CR20R21)tarilo opcionalmente sustituido, - (CR20R21)theterociclilo opcionalmente sustituido, -(CR20R21)tcicloalquiloC3-7 opcionalmente sustituido o -(CR20R21)tcicloalqueniloC3-7 opcionalmente sustituido; o R16 y R17, junto con el átomo de nitrogeno al que están unidos, forman un anillo de cinco a seis miembros opcionalmente sustituido que opcionalmente contiene al menos un heteroátomo adicional seleccionado entre oxígeno, azufre y N-R15; cada uno de R18 y R19 se selecciona independientemente entre hidrogeno y alquilo C1-6 opcionalmente sustituido con hasta dos grupos hidroxi; o R18 y R19, junto con el átomo de nitrogeno al que están unidos, forman un anillo de cinco a seis miembros, que opcionalmente contiene un heteroátomo adicional seleccionado entre oxígeno, azufre y N-R15, y donde el anillo está opcionalmente sustituido con hasta dos grupos seleccionados independientemente entre oxo, halogeno y alquilo C1-6; R20 y R21 se seleccionan independientemente entre hidrogeno o alquilo C1-4; m es 0 o un numero entero seleccionado entre 1, 2, 3 y 4; p es 0 o un numero entero seleccionado entre 1 y 2; q es 0 o un numero entero seleccionado entre 1, 2 y 3; r es 0 o el numero entero 1; s es 0 o un numero entero seleccionado entre 1, 2, 3 y 4; y t es 0 o un numero entero seleccionado entre 1, 2, 3, 4, 5 y 6; v es un numero entero seleccionado entre 1, 2, 3, 4, 5 y 6; o una sal farmacéuticamente aceptable o un derivado del mismo. Composicion farmacéutica que los comprende y su uso para la preparacion de dicha composicion farmacéutica util para el tratamiento de una afeccion o estado de enfermedad mediado por la actividad quinasa de p38 o mediado por citoquinas producidas por la actividad quinasa de p38. proceso para preparar dichos compuestos. Se aplican en el tratamiento de la inflamacion y enfermedades cronicas relacionadas.Biphenyl carboxylic acid compounds of the formula (1), wherein R 1 is selected from hydrogen; C1-6 alkyl optionally substituted with up to three groups independently selected from C1-6 alkoxy, halogen and hydroxy; C3-7 cycloalkyl optionally independently substituted with one or more C1-6 alkyl groups; an aryl, heteroaryl, or heterocyclyl ring each optionally substituted, independently, with one to three groups selected from R5 and R6; R2 is hydrogen, C1-6 alkyl or a - (CH2) p3-7 cycloalkyl optionally independently substituted with one or more C1-6 alkyl groups, or (CH2) mR1 and R2, together with the nitrogen atom to which they are attached , form an optionally substituted four to six membered heterocyclic ring, optionally containing another heteroatom selected from O / N / S; R3 is halogen or methyl; R4 is hydrogen, C1-6 alkyl, C1-6 alkyl, haloC1-4 substituted alkyl or C3-7 cycloalkyl; R5 is independently C1-6 alkyl, OR4, - (CH2) p3-7 cycloalkyl optionally independently substituted with one or more C1-6 alkyl groups, -CONR9R10, -NHCOR10, -SO2NHR9, - (CH2) qNHSO2R10, halogen, CN , - (CH2) qNR11R12, and trifluoromethyl; R6 is independently hydrogen, C1-6 alkyl, OR4, halogen, trifluoromethyl and - (CH2) qNR11R12; R8 is selected from hydrogen, C1-6 alkyl, C3-7 cycloalkyl optionally substituted with one or more C1-6 alkyl groups, OH, C1-6 alkyl optionally substituted with one or more hydroxyl groups, CONHR9, phenyl optionally substituted with R13 and / or R14, or a heteroaryl optionally substituted with R13 and / or R14; each of R9 and R10 is independently selected from hydrogen and C1-6 alkyl, or R9 and R10, together with the nitrogen atom to which they are attached, form a five to six membered heterocyclic ring that optionally contains an additional heteroatom selected from oxygen, sulfur and N-R15, where the ring is optionally substituted with up to two C1-6 alkyl groups; R11 is selected from hydrogen, C1-6 alkyl and - (CH2) p3-7 cycloalkyl optionally substituted with one or more C1-6 alkyl groups; R12 is selected from hydrogen and C1-6 alkyl, or R11 and R12, together with the nitrogen atom to which they are attached, form a five or six membered heterocyclic ring that optionally contains an additional heteroatom selected from oxygen, sulfur and N- R15; R13 is selected from C1-6 alkyl, C1-6 alkoxy, - (CH2) p3-7 cycloalkyl optionally substituted with one or more C1-6 alkyl groups, -CONR9R10, -NHCOR10, halogen, CN, - (CH2) qNR11R12 , trifluoromethyl, phenyl optionally independently substituted with one or more R14 groups, heterocyclyl optionally substituted independently with one or more R14 groups, and a heteroaryl optionally substituted independently with one or more R14 groups; R14 is selected from C1-6 alkyl, C1-6 alkoxy, halogen, halo-substituted C1-4 alkyl and NR11R12; R15 is selected from hydrogen and methyl; each of X and Y is independently selected from hydrogen, methyl and halogen; Z is selected from - (CH2) sCOOR16, or - (CH2) sCONR16R17; R16 and R17 are independently selected from hydrogen, optionally substituted C1-6 alkyl, - (CR20R21) vOR18, - (CR20R2I) vNR18R19, - (CR20R21) vNHSO2R18, - (CR20R21) vCONR18R19, - (CR20R21) vCOOR18, - (CR20R21) optionally substituted theteroaryl, - (CR20R21) optionally substituted taryl, - (CR20R21) optionally substituted theterocyclyl, - ((CR20R21) optionally substituted C3-7 cycloalkyl or - (CR20R21) optionally substituted C3-7 tcycloalkenyl; or R16 and R17, together with the nitrogen atom to which they are attached, form an optionally substituted five to six member ring that optionally contains at least one additional heteroatom selected from oxygen, sulfur and N-R15; each of R18 and R19 is independently selected from hydrogen and C1-6 alkyl optionally substituted with up to two hydroxy groups; or R18 and R19, together with the nitrogen atom to which they are attached, form a five to six member ring, which optionally contains an additional heteroatom selected from oxygen, sulfur and N-R15, and where the ring is optionally substituted with up to two groups independently selected from oxo, halogen and C1-6 alkyl; R20 and R21 are independently selected from hydrogen or C1-4 alkyl; m is 0 or an integer selected from 1, 2, 3 and 4; p is 0 or an integer selected between 1 and 2; q is 0 or an integer selected from 1, 2 and 3; r is 0 or the whole number 1; s is 0 or an integer selected from 1, 2, 3 and 4; and t is 0 or an integer selected from 1, 2, 3, 4, 5 and 6; v is an integer selected from 1, 2, 3, 4, 5 and 6; or a pharmaceutically acceptable salt or derivative thereof. Pharmaceutical composition comprising them and their use for the preparation of said pharmaceutical composition useful for the treatment of a disease or disease condition mediated by the kinase activity of p38 or mediated by cytokines produced by the kinase activity of p38. process to prepare said compounds. They are applied in the treatment of inflammation and related chronic diseases.

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US10342786B2 (en) 2017-10-05 2019-07-09 Fulcrum Therapeutics, Inc. P38 kinase inhibitors reduce DUX4 and downstream gene expression for the treatment of FSHD

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