CO5271673A1 - Derivados de acido 1,2,3,4- tetrahidroquinolin-2- carboxilico sustituidos, procedimiento para su preparacion, su uso para la preparacion de medicamentos y medicamentos que contienen estos compuestos - Google Patents

Derivados de acido 1,2,3,4- tetrahidroquinolin-2- carboxilico sustituidos, procedimiento para su preparacion, su uso para la preparacion de medicamentos y medicamentos que contienen estos compuestos

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CO5271673A1
CO5271673A1 CO01008184A CO01008184A CO5271673A1 CO 5271673 A1 CO5271673 A1 CO 5271673A1 CO 01008184 A CO01008184 A CO 01008184A CO 01008184 A CO01008184 A CO 01008184A CO 5271673 A1 CO5271673 A1 CO 5271673A1
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mono
polysubstituted
unsubstituted
unbranched
branched
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Matthias Gerlach
Michael Przewosny
Werner Englberger
Reissmuller Elke
Petra Bloms-Funke
Maul Corinna
Jagusch Utz-Peter
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Gruenenthal Chemie
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Abstract

Derivados de ácido 1,2,3,4-tetrahidroquinolin-2- carboxílico sustituidos de la fórmula general I,<EMI FILE="01008184_1" ID="1" IMF=JPEG >en forma de sus racematos, enantiómeros, diastereómeros, particularmente mezclas de sus enantiómeros o diastereómeros o de un enantiómero o diastereómero individual; sus bases y/o sales con ácidos fisiológicamente tolerables, en la cual ya sea los radicales R1 y R2 en conjunto, no sustituidos o mono o polisustituidos, representan -(CH2)n-, siendo n = 3 a 10, -CH=CH-CH2--CH=CH-CH2-CH2-,-CH2-CH=CH-CH2-, -CH2-CH=CH-CH2-CH2-, -CH2-CH2-CH=CH-CH2-CH2-, -O-CH2-CH2-, -O-CH2-CH2-CH2-, -CH2-O-CH2-, - 2 --CH2-CH2-O-CH2-, <EMI FILE="01008184_2" ID="2" IMF=JPEG >R3 esta elegido del grupo que comprende H; C1-C18-alquilo, C2-C18-alquenilo o C1-C18-alquinilo, cada uno de ellos ramificado o no ramificado, no sustituido o mono o polisustituido, C3-C8-cicloalquilo, saturado o insaturado, no sustituido o mono o polisustituido o un heterociclo correspondiente en donde al menos un átomo de carbono en el ciclo esta sustituido por N, S u O, alquilarilo o alquilheteroarilo, saturado o insaturado no sustituido o mono o polisustituido, arilo o heteroarilo, no sustituido o mono o polisustituido, R4 esta elegido del grupo que comprendeR4a o ZR4a , siendo Z uno de los radicales C1-C6-alquilo, C2-C6-alquenilo o C2-C6-alquinilo, ramificado o no ramificado, no sustituido o mono o polisustituido, estando elegido R4a entre los radicales H; C1-C12-alquilo, C2-C12-alquenilo o C1-C12-alquinilo, ramificado o no ramificado, no sustituido o mono o polisustituido, C3-C8-cicloalquilo, saturado o insaturado, no sustituido o mono o polisustituido o un heterociclo correspondiente en donde al menos un átomo de carbono en el ciclo está sustituido por N, S u 0, arilo o heteroarilo, no sustituido o mono o polisustituido,C(O)R9, C(O)OR9, C(S)R9, C(S)OR9 o S(O2)R9, estando elegido R9 entre H; C1-C10-alquilo, C2-C10-alquenilo o C1-C10-alquinilo, ramificado o no ramificado, no sustituido o mono o polisustituido, C3-C8-, cicloalquilo, saturado o insaturado, no sustituido o mono o polisustituido o un heterociclo correspondiente en donde al menos un átomo de carbono en el ciclo está sustituido por N, S u O, alquilarilo o alquilheteroarilo, no sustituido o mono o polisustituido, arilo o heteroarilo, no sustituido o mono o polisustituido, particularmente fenetilo, 1-adamantilo, 2-adamantilo, 1-naftilo o 2-naftilo, 2 o 3 o 4-piridilo; tiazolilo; SR10, estando elegido R10 entre arilo o heteroarilo no sustituido o mono o polisustituido, C(O)NR11R12, C(O)NR11NR12R13, C(NR11)NR12R13, C(S)NR11NR12 o C (S)NR11NR12R13, estando elegidos R11, R12 y R13 independientemente entre si entre los radicales H, C1-C18-alquilo, C2-C18-alquenilo o C2-C18-alquinilo, ramificados o no ramificados, no sustituidos o mono o polisustituidos; C3-C8-cicloalquilo, saturados o insaturados, no sustituidos o mono o polisustituidos o un heterociclo correspondiente, en que al menos un átomo de carbono en el ciclo está sustituido por N, S u O, alquilarilo o alquilheteroarilo, no sustituido o mono o polisustituido, arilo o heteroarilo, no sustituido o mono o polisustituido; R5, R6, R7 y R8 están elegidos independientemente entre si del grupo que comprende H, F, Cl, Br, I, CN, NO2, C1-C10-alquilo, C2-C10-alquenilo o C2-C10-alquinilo, ramificado o no ramificado o no sustituido o mono o polisustituido, OR14, OC(O)R14, OC(S)R14, C(O)R14, C(O)OR14, C(S)R14, C(S)OR14, SR14, S(O)R14, o S(O2)R14, estando elegido R14 del grupo que comprende H, C1-C10-alquilo, C2-C10-alquenilo o C2-C10-alquinilo, ramificados o no ramificados, no sustituidos o mono o polisustituidos; C3-C8-cicloalquilo, saturados o insaturados, no sustituidos o mono o polisustituidos o un heterociclo correspondiente, en que al menos un átomo de carbono en el ciclo está sustituido por N, S u O, alquilarilo o alquilheteroarilo, no sustituido o mono o polisustituido, arilo o heteroarilo, no sustituido o mono o polisustituido; NR15R16, NR15C(O)R16, C(NR15)NR16R17, NR15C(S)R16, C(S)NR15R16, o C(S)NR15NR16R17 o S(O2)NR15R16, estando elegidos R15, R16 y R17 independientemente entre si entre los radicalesH, O; C1-C18-alquilo, C2-C18-alquenilo o C2-C18-alquinilo, ramificados o no ramificados, no sustituidos o mono o - 3 -polisustituidos; C3-C8-cicloalquilo, saturados o insaturados, no sustituidos o mono o polisustituidos o un heterociclo correspondiente, en que al menos un átomo de carbono en el ciclo está sustituido por N, S u O, alquilarilo o alquilheteroarilo, no sustituido o mono o polisustituido, arilo o heteroarilo, no sustituido o mono o polisustituido; o R15 y R16 o R16 y R17 en conjunto representan un radical C3-C8-cicloalquilo, saturado o insaturado, no sustituido o mono o polisustituido o un heterociclo correspondiente, en que al menos un átomo de carbono en el ciclo está sustituido por N, S u O, o R5 y R6, R6 y R7 o R7 y R8 en conjunto representan=CR18-CH=CH-CH= o =CH-CR18=CH-CH=, estando elegido R18 entreH, F, Cl, Br, I, OH, o - C1-C10 -alquilo, C2-C10 alquenilo o C2-C10-alquinilo, ramificado o no ramificado, no sustituido o mono o polisustituido, con la condición que cuando R1 y R2 en conjunto representan -CH=CH-CH2-o <EMI FILE="01008184_3" ID="3" IMF=JPEG > , y R3 representa (-)p-mentan-3-ol, particularmente mentol o borneol, no son simultáneamente R7 = Cl, y R5, R6 y R8 = H, cuando R1 y R2 en conjunto representan -CH=CH-CH2- y R3 representa CH3, no son simultáneamente R7 = H, Cl u OCH3 y R5, R6 y R8 = H,cuando R1b y R2a en conjunto representan -CH=CH-CH2 y R3 representa H, no son simultáneamente R7 =OCH3 o C(O)NH2, y R5, R6 y R8 = H, R5 y R7 = CH3 y R6 y R8 = H o R5 = OCH3 y R5, R6 y R8 = H,cuando R1b y R2a en conjunto representan u -O-CH2-CH2 y R3 representa C2H5, no son simultáneamente R7 = H, Cl, CH3, OCH3 o NO2 , y R5 , R6 y R8 = H, o R5 = NO2 y R6 , R7 y R8 = H,oR1 esta elegido del grupo que comprende C1-C10-alquilo, ramificado o no ramificado, no sustituido o mono o polisustituido; C3-C8-cicloalquilo, saturado o insaturado, no sustituido o mono o polisustituido o un heterociclo correspondiente, en que al menos un átomo de carbono en el ciclo está sustituido por N, S u O, alquilarilo no sustituido o mono o polisustituido, arilo no sustituido o mono o polisustituido;OR19, SR19, o SO2R19, estando elegido R19 del grupo que comprende C1-C10-alquilo, C2-C10-alquenilo o C2-C10-alquinilo, ramificados o no ramificados, no sustituidos o mono o polisustituidos; C3-C8-cicloalquilo, saturado o insaturado, no sustituido o mono o polisustituido o un heterociclo correspondiente, en que al menos un átomo de carbono en el ciclo está sustituido por N, S u O, alquilarilo, arilo, alquilheteroarilo o heteroarilo, no sustituidos o mono o polisustituidos; R2 esta elegido del grupo que comprende H; C1-C10-alquilo, ramificados o no ramificados, no sustituidos o mono o polisustituidos; fenilo no sustituido o mono o polisustituido, debiendo ser R1 arilo, O-arilo o S-arilo cuando R2 representa fenilo,R3 esta elegido del grupo que comprende H; C1-C18-alquilo, C2-C18-alquenilo o C2-C18-alquinilo, ramificados o no ramificados, no sustituidos o mono o polisustituidos; C3-C8-cicloalquilo, saturados o insaturados, no sustituidos o mono o polisustituidos o heterociclo correspondiente, en que al menos un átomo de carbono en el ciclo está sustituido por N, S u O, alquilarilo o alquilheteroarilo, no sustituido o mono o polisustituido, arilo o heteroarilo, no sustituido o mono; o polisustituido R4 esta elegido del grupo que comprendeR4a o ZR4a , siendo Z uno de los radicales C1-C6 alquilo, C2-C6-alquenilo o C2-C6-alquinilo, ramificados o no ramificados, no sustituidos o mono o polisustituidos, estando elegido R4a entre los radicales H; C1-C12-alquilo, C2-C12-alquenilo o C1-C12-alquinilo, ramificados o no ramificados, no sustituidos o mono o polisustituidos, C3-C8-cicloalquilo, saturado o insaturado, no sustituido o mono o polisustituido o un heterociclo correspondiente en donde al menos un átomo de carbono en el ciclo está sustituido por N, S u O, arilo o heteroarilo, no sustituido o mono o polisustituido, C(O)R9, C(O)OR9, C(S)R9, C(S)OR9 o S (O2)R9, estando elegido R9 entre H; C1-C10-alquilo, C2-C10-alquenilo O C1-C10-alquinilo, ramificado o no ramificado, no sustituido o mono o polisustituido, C3-C8- cicloalquilo, saturado o insaturado, no sustituido o mono o polisustituido o un heterociclo correspondiente en donde al menos un átomo de carbono en el ciclo está sustituido por N, S u O, alquilarilo o alquilheteroarilo, no sustituido o mono o polisustituido, arilo o heteroarilo, no sustituido o mono o polisustituido, particularmente fenetilo, 1-adamantilo, 2-adamantilo, 1-naftilo o 2-naftilo, 2 o 3 o 4-piridilo; tiazolilo; - 4 -SR10, estando elegido R10 entre arilo o heteroarilo no sustituido o mono o polisustituido,C(O)NR11R12, C(O)NR11NR12R13, C(NR11)NR12R13, C(S)NR11NR12 o C(S)NR11NR12R13, estando elegidos R11, R12 y R13 independientemente entre si entre los radicales H, C1-C18-alquilo, C2-C18-alquenilo o C2-C18-alquinilo, ramificados o no ramificados, no sustituidos o mono o polisustituidos; C3-C8-cicloalquilo, saturados o insaturados, no sustituidos o mono o polisustituidos o un heterociclo correspondiente, en que al menos un átomo de carbono en el ciclo está sustituido por N, S u O, alquilarilo o alquilheteroarilo, no sustituido o mono o polisustituido, arilo o heteroarilo, no sustituido o mono o polisustituido; R5, R6 , R7 y R8 están elegidos independientemente entre si del grupo que comprende H, F, Cl, Br, I, CN, NO2, C1-C10-alquilo, C2-C10-alquenilo o C2-C10-alquinilo, ramificado o no ramificado, no sustituido o mono o polisustituido, OR14, OC(O)R14, 0C(S)R14, C(O)R14, C(O)OR14, C(S)R14, C(S)OR14, SR14, S(O)R14, o S(O2)R14, estando elegido R14 del grupo que comprende H, C1-C10-alquilo, C2-C10-alquenilo o C2-C10-alquinilo, ramificados o no ramificados, no sustituidos o mono o polisustituidos; C3-C8-cicloalquilo, saturados o ins
CO01008184A 2000-02-07 2001-02-05 Derivados de acido 1,2,3,4- tetrahidroquinolin-2- carboxilico sustituidos, procedimiento para su preparacion, su uso para la preparacion de medicamentos y medicamentos que contienen estos compuestos CO5271673A1 (es)

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