AR121485A1 - GPR40 AGONISTS - Google Patents

GPR40 AGONISTS

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Publication number
AR121485A1
AR121485A1 ARP210100532A ARP210100532A AR121485A1 AR 121485 A1 AR121485 A1 AR 121485A1 AR P210100532 A ARP210100532 A AR P210100532A AR P210100532 A ARP210100532 A AR P210100532A AR 121485 A1 AR121485 A1 AR 121485A1
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Argentina
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alkyl
cycloalkyl
fluoroalkyl
halogen
unsubstituted
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ARP210100532A
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Spanish (es)
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Iyassu Sebhat
Shuwen He
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Kallyope Inc
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Publication of AR121485A1 publication Critical patent/AR121485A1/en

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Abstract

Esta solicitud está dirigida, al menos en parte, a agonistas de GPR40 útiles para el tratamiento de afecciones o trastornos que involucran el eje intestino-cerebro. En algunas formas de realización, los agonistas de GPR40 son compuestos restringidos al tracto gastrointestinal. En algunas formas de realización, los agonistas de GRP40 son agonistas parciales o agonistas totales. En algunas formas de realización, la afección o trastorno es un trastorno metabólico, tal como diabetes, obesidad, esteatohepatitis no alcohólica (NASH) o un trastorno nutricional como el síndrome del intestino corto. Reivindicación 1: Un compuesto representado por la fórmula (1) o una sal apta para uso farmacéutico, un solvato, un estereoisómero o un profármaco del mismo, siendo que: Z es -P(=O)(H)OR⁶, -P(=O)(R⁵)OR⁶, -P(=O)(OR⁶)₂, -S(=O)(OR⁶), -SO₂OR⁶, -C(=O)NHSO₂R⁵, -C(=O)NHSO₂N(R⁶)₂, -N(R⁶)SO₂N(R⁶)₂, -N(R⁶)C(=O)NHSO₂(R⁵), -N(R⁶)C(=O)NHSO₂N(R⁶)₂, -N(R⁶)C(=NH)NH₂, -C(=O)NHNHC(=O)N(R⁶)₂, o -B(OR⁶)₂; R⁵ es C₁-C₆ alquilo, C₃-C₆ cicloalquilo, fenilo, o -(C₁-C₆ alquil)-fenilo; siendo que cada alquilo, cicloalquilo, y fenilo considerado en forma independiente no está sustituido o está sustituido con 1, 2, ó 3 sustituyentes a seleccionar a partir del conjunto que consiste en halógeno, -CN, -OH, -O-(C₁-C₆ alquil), C₁-C₆ alquilo, C₁-C₆ fluoroalquilo, C₁-C₆ hidroxialquilo, -O-(C₁-C₆ fluoroalquil), C₃-C₆ cicloalquilo, y heterocicloalquilo de 3 a 6 miembros; cada R⁶ considerado en forma independiente es hidrógeno, C₁-C₆ alquilo, C₃-C₆ cicloalquilo, fenilo, o -(C₁-C₆ alquil)-fenilo; siendo que cada alquilo, cicloalquilo, y fenilo considerado en forma independiente no está sustituido o está sustituido con 1, 2, ó 3 sustituyentes a seleccionar a partir del conjunto que consiste en halógeno, -CN, -OH, -O-(C₁-C₆ alquil), C₁-C₆ alquilo, C₁-C₆ fluoroalquilo, C₁-C₆ hidroxialquilo, -O-(C₁-C₆ fluoroalquil), C₃-C₆ cicloalquilo, y heterocicloalquilo de 3 a 6 miembros; R¹, R², y R³ son, considerando cada uno en forma independiente, hidrógeno, halógeno, -OH, -O-(C₁-C₆ alquil), C₁-C₆ alquilo, C₃-C₆ cicloalquilo, o heterocicloalquilo de 3 a 6 miembros; siendo que cada alquilo, cicloalquilo, y heterocicloalquilo considerado en forma independiente no está sustituido o está sustituido con 1, 2, ó 3 sustituyentes a seleccionar a partir del conjunto que consiste en halógeno, -CN, -OH, -O-(C₁-C₆ alquil), y C₁-C₆ alquilo; R⁴ es C₁-C₆ alquilo, C₃-C₆ cicloalquilo, o heterocicloalquilo de 3 a 6 miembros; siendo que cada alquilo, cicloalquilo, y heterocicloalquilo considerado en forma independiente no está sustituido o está sustituido con 1, 2, ó 3 sustituyentes a seleccionar a partir del conjunto que consiste en halógeno, -CN, -OH, -O-(C₁-C₆ alquil), y C₁-C₆ alquilo; Y¹, Y², Y³, y Y⁴ son, considerando cada uno en forma independiente, N, CH, o C-RY; cada RY considerado en forma independiente es halógeno, -CN, -OH, -O-(C₁-C₆ alquil), -NH₂, -NH-(C₁-C₆ alquil), -N(C₁-C₆ alquil)₂, C₁-C₆ alquilo, C₃-C₆ cicloalquilo, o heterocicloalquilo de 3 a 6 miembros; siendo que cada alquilo, cicloalquilo, y heterocicloalquilo considerado en forma independiente no está sustituido o está sustituido con 1, 2, ó 3 sustituyentes a seleccionar a partir del conjunto que consiste en halógeno, -CN, -OH, -O-(C₁-C₆ alquil), y C₁-C₆ alquilo; L¹ es -O-, -NR⁷-, *-O-CH₂-, *-CH₂-O-, *-NR⁷-CH₂-, *-CH₂-NR⁷-, *-NR⁷-C(O)-, *-C(O)-NR⁷-, o *-C(O)-CH₂-; siendo que * representa la conexión con el Anillo B; R⁷ es hidrógeno, C₁-C₆ alquilo, o C₃-C₆ cicloalquilo; Anillo B es cicloalquileno o heterocicloalquileno; siendo que el cicloalquileno o heterocicloalquileno no está sustituido o está sustituido con 1, 2, 3, ó 4 sustituyentes RB; Anillo A es carbociclo o heterociclo; siendo que el carbociclo o heterociclo no está sustituido o está sustituido con 1, 2, 3, 4, ó 5 sustituyentes RA; L² es un enlace, C₁-C₆ alquileno, o -(C₁-C₆ alquilen)-O-; siendo que el alquileno no está sustituido o está sustituido con 1, 2, ó 3 sustituyentes a seleccionar a partir del conjunto que consiste en halógeno, -CN, -OH, C₁-C₆ alquilo, y -O-(C₁-C₆ alquil); cada RA considerado en forma independiente es halógeno, C₁-C₁₀ alquilo, C₂-C₁₀ alquenilo, C₂-C₁₀ alquinilo, C₁-C₁₀ fluoroalquilo, -LA-CN, -LA-OH, -LA-OR¹⁰, -LA-NR¹¹R¹¹, -LA-C(=O)R¹⁰, -LA-C(=O)OR¹¹, -LA-OC(=O)R¹¹, -LA-C(=O)NR¹¹R¹¹, -LA-NR¹¹C(=O)R¹¹, -LA-NR¹¹C(=O)NR¹¹R¹¹, -LA-OC(=O)NR¹¹R¹¹, -LA-NR¹¹C(=O)OR¹⁰, -LA-OC(=O)OR¹⁰, -LA-arilo, -LA-heteroarilo, -LA-(C₃-C₁₀ cicloalquil), o -LA-(heterocicloalquilo de 3 a 10 miembros); siendo que cada alquilo, alquenilo, alquinilo, fluoroalquilo, arilo, heteroarilo, cicloalquilo, y heterocicloalquilo considerado en forma independiente no está sustituido o está sustituido con 1, 2, 3, 4, ó 5 sustituyentes a seleccionar a partir del conjunto que consiste en halógeno, -CN, -OH, C₁-C₆ alquilo, C₁-C₆ fluoroalquilo, C₁-C₆ hidroxialquilo, -O-(C₁-C₆ alquil), y -O-(C₁-C₆ fluoroalquil); cada RB considerado en forma independiente es halógeno, C₁-C₁₀ alquilo, C₂-C₁₀ alquenilo, C₂-C₁₀ alquinilo, C₁-C₁₀ fluoroalquilo, -LB-CN, -LB-OH, -LB-OR¹⁰, -LB-NR¹¹R¹¹, -LB-C(=O)R¹⁰, -LB-C(=O)OR¹¹, -LB-OC(=O)R¹¹, -LB-C(=O)NR¹¹R¹¹, -LB-NR¹¹C(=O)R¹¹, -LB-NR¹¹C(=O)NR¹¹R¹¹, -LB-OC(=O)NR¹¹R¹¹, -LB-NR¹¹C(=O)OR¹⁰, -LB-OC(=O)OR¹⁰, -LB-arilo, -LB-heteroarilo, -LB-(C₃-C₁₀ cicloalquil), o -LB-(heterocicloalquilo de 3 a 10 miembros); siendo que cada alquilo, alquenilo, alquinilo, fluoroalquilo, arilo, heteroarilo, cicloalquilo, y heterocicloalquilo considerado en forma independiente no está sustituido o está sustituido con 1, 2, 3, 4, ó 5 sustituyentes a seleccionar a partir del conjunto que consiste en halógeno, -CN, -OH, C₁-C₆ alquilo, C₁-C₆ fluoroalquilo, C₁-C₆ hidroxialquilo, -O-(C₁-C₆ alquil), y -O-(C₁-C₆ fluoroalquil); cada LA y LB considerado en forma independiente es un enlace o C₁₋₆ alquileno; siendo que el alquileno no está sustituido o está sustituido con 1, 2, ó 3 sustituyentes a seleccionar a partir del conjunto que consiste en halógeno, -CN, -OH, -O-(C₁-C₆ alquil), y C₁-C₆ alquilo; cada R¹⁰ considerado en forma independiente es C₁-C₁₀ alquilo, C₂-C₁₀ alquenilo, C₂-C₁₀ alquinilo, C₃-C₁₀ cicloalquilo, heterocicloalquilo de 3 a 10 miembros, fenilo, o heteroarilo monocíclico; siendo que cada alquilo, alquenilo, alquinilo, fenilo, heteroarilo, cicloalquilo, y heterocicloalquilo considerado en forma independiente no está sustituido o está sustituido con 1, 2, 3, 4, ó 5 sustituyentes a seleccionar a partir del conjunto que consiste en halógeno, -CN, -OH, C₁-C₆ alquilo, C₁-C₆ fluoroalquilo, C₁-C₆ hidroxialquilo, -O-(C₁-C₆ alquil), y -O-(C₁-C₆ fluoroalquil); y cada R¹¹ considerado en forma independiente es hidrógeno, C₁-C₁₀ alquilo, C₂-C₁₀ alquenilo, C₂-C₁₀ alquinilo, C₃-C₁₀ cicloalquilo, heterocicloalquilo de 3 a 10 miembros, fenilo, o heteroarilo monocíclico; siendo que cada alquilo, alquenilo, alquinilo, fenilo, heteroarilo, cicloalquilo, y heterocicloalquilo considerado en forma independiente no está sustituido o está sustituido con 1, 2, 3, 4, ó 5 sustituyentes a seleccionar a partir del conjunto que consiste en halógeno, -CN, -OH, C₁-C₆ alquilo, C₁-C₆ fluoroalquilo, C₁-C₆ hidroxialquilo, -O-(C₁-C₆ alquil), y -O-(C₁-C₆ fluoroalquil); o dos R¹¹ situados en el mismo átomo de nitrógeno tomados en forma conjunta con el átomo de nitrógeno al que están unidos forman un N-heterocicloalquilo de 3 a 10 miembros; siendo que el heterocicloalquilo no está sustituido o está sustituido con 1, 2, 3, 4, ó 5 sustituyentes a seleccionar a partir del conjunto que consiste en halógeno, -CN, -OH, C₁-C₆ alquilo, C₁-C₆ fluoroalquilo, C₁-C₆ hidroxialquilo, -O-(C₁-C₆ alquil), y -O-(C₁-C₆ fluoroalquil).This application is directed, at least in part, to GPR40 agonists useful for the treatment of conditions or disorders involving the gut-brain axis. In some embodiments, the GPR40 agonists are compounds restricted to the gastrointestinal tract. In some embodiments, GRP40 agonists are partial agonists or full agonists. In some embodiments, the condition or disorder is a metabolic disorder, such as diabetes, obesity, nonalcoholic steatohepatitis (NASH), or a nutritional disorder such as short bowel syndrome. Claim 1: A compound represented by formula (1) or a pharmaceutical grade salt, solvate, stereoisomer or prodrug thereof, wherein: Z is -P(=O)(H)OR⁶, -P( =O)(R⁵)OR⁶, -P(=O)(OR⁶)₂, -S(=O)(OR⁶), -SO₂OR⁶, -C(=O)NHSO₂R⁵, -C(=O)NHSO₂N(R⁶) ₂, -N(R⁶)SO₂N(R⁶)₂, -N(R⁶)C(=O)NHSO₂(R⁵), -N(R⁶)C(=O)NHSO₂N(R⁶)₂, -N(R⁶)C (=NH)NH₂, -C(=O)NHNHC(=O)N(R⁶)₂, or -B(OR⁶)₂; R 5 is C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, phenyl, or -(C 1 -C 6 alkyl)-phenyl; wherein each alkyl, cycloalkyl, and phenyl considered independently is either unsubstituted or substituted with 1, 2, or 3 substituents to be selected from the group consisting of halogen, -CN, -OH, -O-(C₁- C 6 alkyl), C 1 -C 6 alkyl, C 1 -C 6 fluoroalkyl, C 1 -C 6 hydroxyalkyl, -O-(C 1 -C 6 fluoroalkyl), C 3 -C 6 cycloalkyl, and 3- to 6-membered heterocycloalkyl; each R⁶ taken independently is hydrogen, C₁-C₆ alkyl, C₃-C₆ cycloalkyl, phenyl, or -(C₁-C₆ alkyl)-phenyl; wherein each alkyl, cycloalkyl, and phenyl considered independently is either unsubstituted or substituted with 1, 2, or 3 substituents to be selected from the group consisting of halogen, -CN, -OH, -O-(C₁- C 6 alkyl), C 1 -C 6 alkyl, C 1 -C 6 fluoroalkyl, C 1 -C 6 hydroxyalkyl, -O-(C 1 -C 6 fluoroalkyl), C 3 -C 6 cycloalkyl, and 3- to 6-membered heterocycloalkyl; R¹, R², and R³ are, each considered independently, hydrogen, halogen, -OH, -O-(C₁-C₆ alkyl), C₁-C₆ alkyl, C₃-C₆ cycloalkyl, or 3- to 6-membered heterocycloalkyl; wherein each alkyl, cycloalkyl, and heterocycloalkyl considered independently is unsubstituted or substituted with 1, 2, or 3 substituents to be selected from the group consisting of halogen, -CN, -OH, -O-(C₁- C₆ alkyl), and C₁-C₆ alkyl; R⁴ is C₁-C₆ alkyl, C₃-C₆ cycloalkyl, or 3-6 membered heterocycloalkyl; wherein each alkyl, cycloalkyl, and heterocycloalkyl considered independently is unsubstituted or substituted with 1, 2, or 3 substituents to be selected from the group consisting of halogen, -CN, -OH, -O-(C₁- C₆ alkyl), and C₁-C₆ alkyl; Y¹, Y², Y³, and Y⁴ are each considered independently to be N, CH, or C-RY; each RY taken independently is halogen, -CN, -OH, -O-(C 1 -C 6 alkyl), -NH 2 , -NH-(C 1 -C 6 alkyl), -N(C 1 -C 6 alkyl) 2 , C 1 - C₆ alkyl, C₃-C₆ cycloalkyl, or 3-6 membered heterocycloalkyl; wherein each alkyl, cycloalkyl, and heterocycloalkyl considered independently is unsubstituted or substituted with 1, 2, or 3 substituents to be selected from the group consisting of halogen, -CN, -OH, -O-(C₁- C₆ alkyl), and C₁-C₆ alkyl; L¹ is -O-, -NR⁷-, *-O-CH₂-, *-CH₂-O-, *-NR⁷-CH₂-, *-CH₂-NR⁷-, *-NR⁷-C(O)-, *- C(O)-NR⁷-, or *-C(O)-CH₂-; where * represents the connection with Ring B; R⁷ is hydrogen, C₁-C₆ alkyl, or C₃-C₆ cycloalkyl; Ring B is cycloalkylene or heterocycloalkylene; wherein the cycloalkylene or heterocycloalkylene is unsubstituted or substituted with 1, 2, 3, or 4 RB substituents; Ring A is carbocycle or heterocycle; wherein the carbocycle or heterocycle is unsubstituted or substituted with 1, 2, 3, 4, or 5 RA substituents; L² is a bond, C 1 -C 6 alkylene, or -(C 1 -C 6 alkylene)-O-; wherein alkylene is unsubstituted or substituted with 1, 2, or 3 substituents to be selected from the group consisting of halogen, -CN, -OH, C₁-C₆ alkyl, and -O-(C₁-C₆ alkyl) ; each RA considered independently is halogen, C₁-C₁₀ alkyl, C₂-C₁₀ alkenyl, C₂-C₁₀ alkynyl, C₁-C₁₀ fluoroalkyl, -LA-CN, -LA-OH, -LA-OR¹⁰, -LA-NR¹¹R¹¹, - LA-C(=O)R¹⁰, -LA-C(=O)OR¹¹, -LA-OC(=O)R¹¹, -LA-C(=O)NR¹¹R¹¹, -LA-NR¹¹C(=O)R¹¹, - LA-NR¹¹C(=O)NR¹¹R¹¹, -LA-OC(=O)NR¹¹R¹¹, -LA-NR¹¹C(=O)OR¹⁰, -LA-OC(=O)OR¹⁰, -LA-aryl, -LA-heteroaryl, - LA-(C 3 -C 10 cycloalkyl), or -LA-(3- to 10-membered heterocycloalkyl); where each alkyl, alkenyl, alkynyl, fluoroalkyl, aryl, heteroaryl, cycloalkyl, and heterocycloalkyl considered independently is unsubstituted or is substituted with 1, 2, 3, 4, or 5 substituents to be selected from the group consisting of halogen, -CN, -OH, C 1 -C 6 alkyl, C 1 -C 6 fluoroalkyl, C 1 -C 6 hydroxyalkyl, -O-(C 1 -C 6 alkyl), and -O-(C 1 -C 6 fluoroalkyl); each RB considered independently is halogen, C₁-C₁₀ alkyl, C₂-C₁₀ alkenyl, C₂-C₁₀ alkynyl, C₁-C₁₀ fluoroalkyl, -LB-CN, -LB-OH, -LB-OR¹⁰, -LB-NR¹¹R¹¹, - LB-C(=O)R¹⁰, -LB-C(=O)OR¹¹, -LB-OC(=O)R¹¹, -LB-C(=O)NR¹¹R¹¹, -LB-NR¹¹C(=O)R¹¹, - LB-NR¹¹C(=O)NR¹¹R¹¹, -LB-OC(=O)NR¹¹R¹¹, -LB-NR¹¹C(=O)OR¹⁰, -LB-OC(=O)OR¹⁰, -LB-aryl, -LB-heteroaryl, - LB-(C 3 -C 10 cycloalkyl), or -LB-(3 to 10 membered heterocycloalkyl); where each alkyl, alkenyl, alkynyl, fluoroalkyl, aryl, heteroaryl, cycloalkyl, and heterocycloalkyl considered independently is unsubstituted or is substituted with 1, 2, 3, 4, or 5 substituents to be selected from the group consisting of halogen, -CN, -OH, C 1 -C 6 alkyl, C 1 -C 6 fluoroalkyl, C 1 -C 6 hydroxyalkyl, -O-(C 1 -C 6 alkyl), and -O-(C 1 -C 6 fluoroalkyl); each LA and LB taken independently is a bond or C₁₋₆ alkylene; wherein alkylene is unsubstituted or substituted with 1, 2, or 3 substituents to be selected from the group consisting of halogen, -CN, -OH, -O-(C 1 -C 6 alkyl), and C 1 -C 6 alkyl ; each R 10 taken independently is C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 3 -C 10 cycloalkyl, 3- to 10-membered heterocycloalkyl, phenyl, or monocyclic heteroaryl; wherein each alkyl, alkenyl, alkynyl, phenyl, heteroaryl, cycloalkyl, and heterocycloalkyl taken independently is unsubstituted or substituted with 1, 2, 3, 4, or 5 substituents selected from the group consisting of halogen, -CN, -OH, C 1 -C 6 alkyl, C 1 -C 6 fluoroalkyl, C 1 -C 6 hydroxyalkyl, -O-(C 1 -C 6 alkyl), and -O-(C 1 -C 6 fluoroalkyl); and each R 11 taken independently is hydrogen, C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 3 -C 10 cycloalkyl, 3- to 10-membered heterocycloalkyl, phenyl, or monocyclic heteroaryl; wherein each alkyl, alkenyl, alkynyl, phenyl, heteroaryl, cycloalkyl, and heterocycloalkyl taken independently is unsubstituted or substituted with 1, 2, 3, 4, or 5 substituents selected from the group consisting of halogen, -CN, -OH, C 1 -C 6 alkyl, C 1 -C 6 fluoroalkyl, C 1 -C 6 hydroxyalkyl, -O-(C 1 -C 6 alkyl), and -O-(C 1 -C 6 fluoroalkyl); or two R¹¹ located on the same nitrogen atom taken together with the nitrogen atom to which they are attached form a 3 to 10 membered N-heterocycloalkyl; wherein heterocycloalkyl is unsubstituted or substituted with 1, 2, 3, 4, or 5 substituents to be selected from the group consisting of halogen, -CN, -OH, C 1 -C 6 alkyl, C 1 -C 6 fluoroalkyl, C 1 -C 6 hydroxyalkyl, -O-(C 1 -C 6 alkyl), and -O-(C 1 -C 6 fluoroalkyl).

ARP210100532A 2020-02-28 2021-03-01 GPR40 AGONISTS AR121485A1 (en)

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