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AR044496A1 - N-ARILHETEROCICLOS REPLACED, PROCEDURES FOR THEIR PREPARATION, AND ITS EMPLOYMENT AS MEDICATIONS - Google Patents

N-ARILHETEROCICLOS REPLACED, PROCEDURES FOR THEIR PREPARATION, AND ITS EMPLOYMENT AS MEDICATIONS

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Publication number
AR044496A1
AR044496A1 ARP040100469A ARP040100469A AR044496A1 AR 044496 A1 AR044496 A1 AR 044496A1 AR P040100469 A ARP040100469 A AR P040100469A AR P040100469 A ARP040100469 A AR P040100469A AR 044496 A1 AR044496 A1 AR 044496A1
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Argentina
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alkyl
independently
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aryl
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Aventis Pharma Gmbh
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Publication of AR044496A1 publication Critical patent/AR044496A1/en

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Abstract

N-arilheterociclos substituidos, sus sales fisiológicamente tolerables y derivados fisiológicamente funcionales. Los compuestos son útiles como aneroxígenos. Reivindicación 1: Un compuesto de fórmula (1) en la cual R1, R2 significan de manera independiente H, alquilo C1-8, -(CR78R79)o-R12, alcoxi C1-4-alquilo C1-4, ariloxi-alquilo C1-4, alquenilo C3-8, alquinilo C3-8, CO-alquilo C1-8, -CO-(CH2)o-R12, CO-ariloxi-alquilo C1-4, CO-alquenilo C2-8, CO-alquinilo C2-8, COCH-CH(R13), COCC(R14), CO-alquil C1-4-S(O)p-alquilo C1-4, CO(C(R15)(R16))qN(R17)(R18), CO(C(R19)(R20))rCON(R21)(R22) o CO(C(R23)(R24))sO(R25); o bien R1 y R2, forman junto con el átomo de nitrógeno al cual están unidos, un anillo mono-, bi- o espirocíclico de 4 a 10 eslabones que además del átomo de nitrógeno, puede contener o a 4 heteroátomos adicionales seleccionados del grupo de oxígeno, nitrógeno y azufre, pudiendo el sistema anular heterocíclico estar substituido adicionalmente con F, Cl, Br, CF3, NO2, CN, alquilo C1-6, O-alquilo C1-8, alcoxi C1-4-alquilo C1-4, hidroxi-alquilo C1-4, alquilen C0-8-arilo, oxo, CO(R26), CON(R27)(R28), hidroxi, COO(R29), N(R30)COalquilo C1-6, N(R31)(R32) o SO2CH3; o vale 0, 1, 2, 3, 4, 5 ó 6; p vale 0, 1 ó 2; q, r, s valen de manera independiente 0, 1, 2, 3 ó 4; R13, R14 significan de manera independiente entre sí, un sistema anular aromático de 5 a 10 eslabones, que puede contener 0-2 heteroátomos adicionales del grupo de nitrógeno, oxígeno y azufre, y que puede estar substituido con F, Cl, Br, CF3, NO2, CN, alquilo C1-6 o O-alquilo C1-8; R15, R16, R17, R19, R20, R21, R22, R23, R24, R25, R26, R27, R28, R29, R30, R31, R32 significan de manera independiente entre sí H o alquilo C1-6; R18 significa H, alquilo C1-6, COalquilo C1-6 o CO(R33); o bien R17 y R18, R21 y R22, R27 y R28, y R31 y R32, significan de manera independiente entre sí, y opcionalmente junto con el átomo de nitrógeno al cual al cual están unidos, un anillo de 5-6 eslabones que, además del átomo de nitrógeno, puede contener aún 0-1 heteroátomos adicionales del grupo de N-alquilo C1-6, oxígeno y azufre; R33 significa un sistema anular aromático de 5-10 eslabones, que puede contener 0-2 heteroátomos adicionales del grupo de nitrógeno, oxígeno y azufre, y que puede estar substituido con F, Cl, Br, CF3, NO2, CN, alquilo C1-6 o O-alquilo C1-8; R12 significa OH, O-alquilo C1-6, Oalquilen C0-8-arilo, CN, S-alquilo C1-6, COO(R80), CON(R81)(R93), N(R82)(R83) o anillo mono-, bi- o espirocíclico de 3-12 eslabones, que puede contener uno o varios heteroátomos del grupo de N, O y S, y el anillo de 3-12 eslabones puede contener substituyentes adicionales tales como F, Cl, Br, I, OH, CF3, NO2, CN, OCF3, oxo, O-alquilo C1-6, alcoxi C1-4-alquilo C1-4, S-alquilo C1-6, alquilo C1-6, alquenilo C2-6, cicloalquilo C3-8, O-cicloalquilo C3-8, cicloalquenilo C3-8, O-cicloalquenilo C3-8, alquinilo C2-6, O-alquilen C0-8-arilo, N(R34)(R35), COCH-CH(R36), (C(R37)(R38))t(R39), CO(C(R37)(R38))t(R39), COalquilo C1-6, COCOOalquilo C1-6, COO(R40), S(O)u(R41) o COOH; t vale 0, 1, 2, 3, 4, 5 ó 6; u vale 0, 1 ó 2; o bien R34, R35, R37, R38 significan de manera independiente entre sí H o alquilo C1-8; R34 y R35, significan opcionalmente junto con el átomo de nitrógeno al cual al cual están unidos, un anillo de 5-6 eslabones que, además del átomo de nitrógeno, puede contener aún 0-1 heteroátomos adicionales del grupo de N-alquilo C1-6, oxígeno y azufre, y opcionalmente puede estar substituido con 1 o 2 grupos oxo; R36, R39 significan de manera independiente entre sí cicloalquilo C3-8, un sistema anular aromático de 5-10 eslabones, que puede contener 0-2 heteroátomos adicionales del grupo de nitrógeno, oxígeno y azufre, y que puede estar substituido con F, Cl, Br, CF3, NO2, CN, alquilo C1-6 o O-alquilo C1-8; R40 significa H, alquilo C1-8, alquenilo C2-6 o alquilen C0-8-arilo; R41 significa alquilo C1-8, un sistema anular aromático de 5-10 eslabones, que puede contener 0-2 heteroátomos adicionales del grupo de nitrógeno, oxígeno y azufre, y que puede estar substituido con F, Cl, Br, CF3, NO2, CN, alquilo C1-6 o O-alquilo C1-8; R78, R79 significan de manera independiente entre sí H, alquilo C1-8, hidroxi-alquilo C1-4, OH o alcoxi C1-4-alquilo C1-4; R80, R81, R93 significan de manera independiente entre sí alquilo C1-8, alquenilo C2-6, alquilen C0-8-arilo; R82, R83 significan de manera independiente entre sí H o alquilo C1-6; o bien R82 y R83, significan, opcionalmente junto con el átomo de nitrógeno al cual al cual están unidos, un anillo de 5-6 eslabones que, además del átomo de nitrógeno, puede contener aún 0-1 heteroátomos adicionales del grupo de N-alquilo C1-6, oxígeno y azufre, y opcionalmente puede estar substituido con 1 o 2 grupos oxo; R3 significa H, alquilo C1-6; R4, R5 significan, de manera independiente entre sí H, alquilo C1-6, OH, O-alquilo C1-6, O-COalquilo C1-6 o S-alquilo C1-6; o bien R6, R7, R8, R9 significan de manera independiente entre sí H o alquilo C1-8; o bien R6 y R7, y R8 y R9, significan de manera independiente entre sí y opcionalmente, oxo; n, m valen de manera independiente entre sí 0, 1 o 2; A, B, D, G significan de manera independiente entre sí N o C(R42); o bien los grupos A y B, o los grupos D y G son en cada caso C(R42) y forman juntos un radical carbocíclico o heterocíclico de 5 o 6 eslabones, de manera tal que se origina en conjunto un sistema bicíclico; R42 significa H, F, Cl, Br, I, OH, CF3, NO2, CN, OCF3, O-alquilo C1-6, O-alcoxi C1-4-alquilo C1-4, S-alquilo C1-6, alquilo C1-6, alquenilo C2-6, cicloalquilo C3-8, O-cicloalquilo C3-8, cicloalquenilo C3-8, O-cicloalquenilo C3-8, alquinilo C2-6, alquilenC0-8-arilo, O-alquilen C0-8-arilo, S-arilo, N(R43)(R44), SO2-CH3, COOH, COO-alquilo C1-6, CON(R45)(R46), N(R47)CO(R48), N(R49)SO2(R50), CO(R51), -(CR84R85)x-O(R86); R43, R44, R45, R46, R47, R49 significan de manera independiente entre sí H o alquilo C1-8; o bien R43 y R44, y R45 y R46, significan de manera independiente entre sí y opcionalmente junto con el átomo de nitrógeno al cual al cual están unidos, un anillo de 5-6 eslabones que, además del átomo de nitrógeno, puede contener aún 0-1 heteroátomos adicionales del grupo de N-alquilo C1-6, oxígeno y azufre; R48, R50, R51 significan de manera independiente entre sí H, alquilo C1-8 o arilo; R84, R85 significan de manera independiente entre sí H o alquilo C1-8; R86 significa H, alquilo C1-6 o arilo; x vale 1, 2, 3, 4, 5 ó 6; R10 significa H, alquilo C1-8, alquenilo C3-6 o alquinilo C3-6; X significa N(R52), O, un enlace, C=C, C(R53)(R54), C(R55)(R56)O, CO, C:::C, o un grupo de fórmula -(CR87R88)y-, en la cual uno o más grupos -(CR87R88)- pueden haber sido reemplazados por Y, originándose un radical químicamente con sentido; Y significa O, S o N(R89); R52, R53, R54, R55, R56 significan, de manera independiente entre sí H o alquilo C1-8; R87, R88 significan de manera independiente entre sí H o alquilo C1-4, pudiendo tener R87 y R88 en los grupos "y", en cada caso, los mismos significados o significados diferentes; y vale 2, 3, 4, 5 ó 6; E significa una estructura anular carbo- o heterocíclica, bivalente de 3 a 14 eslabones, y con 0 a 4 heteroátomos del grupo de N, O y S, que opcionalmente puede portar substituyentes del grupo de H, F, Cl, Br, I, OH, CF3, NO2, CN, OCF3, oxo, O-alquilo C1-6, O-alcoxi C1-4-alquilo C1-4, S-alquilo C1-6, alquilo C1-6, alquenilo C2-6, cicloalquilo C3-8, O-cicloalquilo C3-8, cicloalquenilo C3-8, O-cicloalquenilo C3-8, alquinilo C2-6, alquilen C0-8-arilo, O-alquilen C0-8-arilo, S-arilo, N(R57)(R58), SO2-CH3, COOH, COO-alquilo C1-6, CON(R59)(R60), N(R61)CO(R62), N(R63)SO2(R64), CO(R65) y que puede ser mono- o bicíclica; R57, R58, R59, R60, R61, R63 significan de manera independiente entre sí H o alquilo C1-8; o bien R57 y R58, y R59 y R60, significan de manera independiente entre sí y opcionalmente junto con el átomo de nitrógeno al cual al cual están unidos, un anillo de 5-6 eslabones que, además del átomo de nitrógeno, puede contener aún 0-1 heteroátomos adicionales del grupo de N-alquilo C1-6, oxígeno y azufre; R62, R64, R65 significan de manera independiente entre sí H, alquilo C1-8, arilo; K significa un enlace, O, OCH2, CH2O, S, SO, SO2, N(R66), N(R67)CO, CON(R68), (C(R69)(R70))v, CO, C:::C, C=C un grupo de fórmula -(CR90R91)z-, en donde uno o varios grupos -(CR90R91)- pueden haber sido reemplazados por Z, originándose un radical químicamente con sentido; v vale 1, 2, 3 ó 4; R66, R67, R68, R69, R70 significan de manera independiente entre sí H o alquilo C1-8; Z significa O, S, N(R92), CO, SO o SO2; R90, R91 significan de manera independiente entre sí H, alquilo C1-8, hidroxi-alquilo C1-4, hidroxi, alcoxi C1-4-alquilo C1-4, y pudiendo tener R90 y R91 en los grupos "z" en cada caso los mismos significados o significados diferentes; z vale 2, 3, 4, 5 ó 6; R92 significa H o alquilo C1-8; R11 significa H, alquilo C1-8, alcoxi C1-4-alquilo C1-4, alquenilo C3-8, alquinilo C3-8, un anillo mono-, bi-, tri- o espirocíclico, de 3 a 10 eslabones que puede contener 1, 2, 3 o 4 heteroátomos seleccionados del grupo de oxígeno, nitrógeno y azufre, pudiendo estar el sistema anular substituido adicionalmente con F, Cl, Br, CF3, NO2, CN, alquilo, O-alquilo C1-8, alcoxi C1-4-alquilo C1-4, alquilen C0-8-arilo, oxo, CO(R71), CON(R72)(R73), hidroxi, hidroxi-alquilo C1-4, COO(R74), N(R75)COalquilo C1-6, N(R76)(R77), SO2CH3 o SCF3; R71, R72, R73, R74, R75, R76, R77 significan de manera independiente entre sí y opcionalmente junto con el átomo de nitrógeno al cual al cual están unidos, un anillo de 5-6 eslabones que, además del átomo de nitrógeno, puede contener aún 0-1 heteroátomos adicionales del grupo de N-alquilo C1-6, oxígeno y azufre; o bien E, K y R11 forman juntos un triciclo, pudiendo ser los anillos, de manera independiente entre sí, saturados, parcialmente saturados o insaturados, y pudiendo contener en cada caso 3-8 átomos en el anillo; sus N-óxidos y sus sales fisiológicamente tolerables.N-substituted arylheterocycles, their physiologically tolerable salts and physiologically functional derivatives. The compounds are useful as anaerogens. Claim 1: A compound of formula (1) in which R1, R2 independently mean H, C1-8 alkyl, - (CR78R79) or-R12, C1-4 alkoxy-C1-4 alkyl, aryloxy-C1-alkyl 4, C3-8 alkenyl, C3-8 alkynyl, CO- C1-8 alkyl, -CO- (CH2) or -R12, CO-aryloxy-C1-4 alkyl, CO-C2-8 alkenyl, CO-C2 alkynyl 8, COCH-CH (R13), COCC (R14), CO-C 1-4 alkyl-S (O) p-C 1-4 alkyl, CO (C (R15) (R16)) qN (R17) (R18), CO (C (R19) (R20)) rCON (R21) (R22) or CO (C (R23) (R24)) sO (R25); or R1 and R2 together with the nitrogen atom to which they are attached, a mono-, bi- or spirocyclic ring of 4 to 10 links which, in addition to the nitrogen atom, may contain or 4 additional heteroatoms selected from the oxygen group , nitrogen and sulfur, the heterocyclic ring system being able to be additionally substituted with F, Cl, Br, CF3, NO2, CN, C1-6 alkyl, O-C1-8 alkyl, C1-4 alkoxy-C1-4 alkyl, hydroxy- C1-4 alkyl, C0-8-aryl alkylene, oxo, CO (R26), CON (R27) (R28), hydroxy, COO (R29), N (R30) C1-6 alkyl, N (R31) (R32) or SO2CH3; or is worth 0, 1, 2, 3, 4, 5 or 6; p is worth 0, 1 or 2; q, r, s are worth 0, 1, 2, 3 or 4 independently; R13, R14 independently mean to each other, an aromatic ring system of 5 to 10 links, which may contain 0-2 additional heteroatoms of the nitrogen, oxygen and sulfur group, and which may be substituted with F, Cl, Br, CF3 , NO2, CN, C1-6 alkyl or O-C1-8 alkyl; R15, R16, R17, R19, R20, R21, R22, R23, R24, R25, R26, R27, R28, R29, R30, R31, R32 independently mean each other H or C1-6 alkyl; R18 means H, C1-6 alkyl, CO C1-6 alkyl or CO (R33); or R17 and R18, R21 and R22, R27 and R28, and R31 and R32, mean independently of each other, and optionally together with the nitrogen atom to which they are attached, a ring of 5-6 links that, in addition to the nitrogen atom, it may still contain 0-1 additional heteroatoms of the N- C1-6 alkyl, oxygen and sulfur group; R33 means an aromatic ring system of 5-10 links, which may contain 0-2 additional hetero atoms of the nitrogen, oxygen and sulfur group, and which may be substituted with F, Cl, Br, CF3, NO2, CN, C1- alkyl 6 or O-C1-8 alkyl; R12 means OH, O-C1-6 alkyl, C0-8-alkyl aryl, CN, S-C1-6 alkyl, COO (R80), CON (R81) (R93), N (R82) (R83) or mono ring -, bi- or spirocyclic of 3-12 links, which may contain one or more heteroatoms of the group of N, O and S, and the 3-12 link ring may contain additional substituents such as F, Cl, Br, I, OH, CF3, NO2, CN, OCF3, oxo, O-C1-6 alkyl, C1-4 alkoxy-C1-4 alkyl, S-C1-6 alkyl, C1-6 alkyl, C2-6 alkenyl, C3-8 cycloalkyl , C3-8 O-cycloalkyl, C3-8 cycloalkenyl, C3-8 O-cycloalkenyl, C2-6 alkynyl, C0-8 -alkyl-aryl, N (R34) (R35), COCH-CH (R36), ( C (R37) (R38)) t (R39), CO (C (R37) (R38)) t (R39), CO C1-6 alkyl, COCOO C1-6 alkyl, COO (R40), S (O) or (R41 ) or COOH; t is worth 0, 1, 2, 3, 4, 5 or 6; u is worth 0, 1 or 2; or R34, R35, R37, R38 independently mean each other H or C1-8 alkyl; R34 and R35, optionally mean together with the nitrogen atom to which they are attached, a ring of 5-6 links which, in addition to the nitrogen atom, can still contain 0-1 additional heteroatoms of the N-C1-C-alkyl group 6, oxygen and sulfur, and may optionally be substituted with 1 or 2 oxo groups; R36, R39 independently mean C3-8 cycloalkyl, an aromatic ring system of 5-10 links, which may contain 0-2 additional heteroatoms of the nitrogen, oxygen and sulfur group, and which may be substituted with F, Cl , Br, CF3, NO2, CN, C1-6 alkyl or O-C1-8 alkyl; R40 means H, C1-8 alkyl, C2-6 alkenyl or C0-8-aryl alkylene; R41 means C1-8 alkyl, an aromatic ring system of 5-10 links, which may contain 0-2 additional hetero atoms of the nitrogen, oxygen and sulfur group, and which may be substituted with F, Cl, Br, CF3, NO2, CN, C1-6 alkyl or O-C1-8 alkyl; R78, R79 independently mean each other H, C1-8 alkyl, hydroxy-C1-4 alkyl, OH or C1-4 alkoxy-C1-4 alkyl; R80, R81, R93 independently mean each other C1-8 alkyl, C2-6 alkenyl, C0-8-aryl alkylene; R82, R83 independently mean each other H or C1-6 alkyl; or R82 and R83, optionally, together with the nitrogen atom to which they are attached, a ring of 5-6 links which, in addition to the nitrogen atom, can still contain 0-1 additional heteroatoms of the group of N- C1-6 alkyl, oxygen and sulfur, and may optionally be substituted with 1 or 2 oxo groups; R3 means H, C1-6 alkyl; R4, R5 independently mean H, C1-6 alkyl, OH, O-C1-6 alkyl, O-CO C1-6 alkyl or S-C1-6 alkyl; or R6, R7, R8, R9 independently mean H or C1-8 alkyl; or R6 and R7, and R8 and R9, mean independently of each other and optionally, oxo; n, m are worth 0, 1 or 2 independently of each other; A, B, D, G independently mean each other N or C (R42); Either groups A and B, or groups D and G are in each case C (R42) and together form a carbocyclic or heterocyclic radical of 5 or 6 links, so that a bicyclic system originates together; R42 means H, F, Cl, Br, I, OH, CF3, NO2, CN, OCF3, O-C1-6 alkyl, O-C1-4 alkoxy-C1-4 alkyl, S-C1-6 alkyl, C1 alkyl -6, C2-6 alkenyl, C3-8 cycloalkyl, O3-8 cycloalkyl, C3-8 cycloalkenyl, C3-8 O-cycloalkenyl, C2-6 alkynyl, C0-8-aryl, O-C0-8 alkylene aryl, S-aryl, N (R43) (R44), SO2-CH3, COOH, COO-C1-6 alkyl, CON (R45) (R46), N (R47) CO (R48), N (R49) SO2 ( R50), CO (R51), - (CR84R85) xO (R86); R43, R44, R45, R46, R47, R49 independently mean each other H or C1-8 alkyl; or R43 and R44, and R45 and R46, mean independently of each other and optionally together with the nitrogen atom to which they are attached, a ring of 5-6 links that, in addition to the nitrogen atom, can still contain 0-1 additional heteroatoms of the N-C1-6 alkyl, oxygen and sulfur group; R48, R50, R51 independently mean each other H, C1-8 alkyl or aryl; R84, R85 independently mean each other H or C1-8 alkyl; R86 means H, C1-6 alkyl or aryl; x is worth 1, 2, 3, 4, 5 or 6; R10 means H, C1-8 alkyl, C3-6 alkenyl or C3-6 alkynyl; X means N (R52), O, a bond, C = C, C (R53) (R54), C (R55) (R56) O, CO, C ::: C, or a group of formula - (CR87R88) and-, in which one or more groups - (CR87R88) - may have been replaced by Y, originating a chemically meaningful radical; Y means O, S or N (R89); R52, R53, R54, R55, R56 means, independently of each other H or C1-8 alkyl; R87, R88 independently mean each other H or C1-4 alkyl, and R87 and R88 may have in the groups "and", in each case, the same different meanings or meanings; and is worth 2, 3, 4, 5 or 6; E means a carbo- or heterocyclic ring structure, bivalent from 3 to 14 links, and with 0 to 4 heteroatoms of the group of N, O and S, which may optionally carry substituents of the group of H, F, Cl, Br, I, OH, CF3, NO2, CN, OCF3, oxo, O-C1-6 alkyl, O-C1-4 alkoxy-C1-4 alkyl, S-C1-6 alkyl, C1-6 alkyl, C2-6 alkenyl, C3 cycloalkyl -8, C3-8 O-cycloalkyl, C3-8 cycloalkenyl, C3-8 O-cycloalkenyl, C2-6 alkynyl, C0-8-aryl alkylene, C0-8-aryl-O-alkylene, S-aryl, N (R57 ) (R58), SO2-CH3, COOH, COO-C1-6 alkyl, CON (R59) (R60), N (R61) CO (R62), N (R63) SO2 (R64), CO (R65) and that it can be mono- or bicyclic; R57, R58, R59, R60, R61, R63 independently mean each other H or C1-8 alkyl; or R57 and R58, and R59 and R60, mean independently of each other and optionally together with the nitrogen atom to which they are attached, a ring of 5-6 links that, in addition to the nitrogen atom, can still contain 0-1 additional heteroatoms of the N-C1-6 alkyl, oxygen and sulfur group; R62, R64, R65 independently mean each other H, C1-8 alkyl, aryl; K means a link, O, OCH2, CH2O, S, SO, SO2, N (R66), N (R67) CO, CON (R68), (C (R69) (R70)) v, CO, C ::: C, C = C a group of formula - (CR90R91) z-, where one or more groups - (CR90R91) - may have been replaced by Z, giving rise to a chemically meaningful radical; v is worth 1, 2, 3 or 4; R66, R67, R68, R69, R70 independently mean each other H or C1-8 alkyl; Z means O, S, N (R92), CO, SO or SO2; R90, R91 independently mean each other H, C1-8 alkyl, hydroxy-C1-4 alkyl, hydroxy, C1-4 alkoxy-C1-4 alkyl, and R90 and R91 may be in groups "z" in each case the same meanings or different meanings; z is worth 2, 3, 4, 5 or 6; R92 means H or C1-8 alkyl; R11 means H, C1-8 alkyl, C1-4 alkoxy-C1-4 alkyl, C3-8 alkenyl, C3-8 alkynyl, a mono-, bi-, tri- or spirocyclic ring, of 3 to 10 links that may contain 1, 2, 3 or 4 heteroatoms selected from the group of oxygen, nitrogen and sulfur, the ring system being able to be additionally substituted with F, Cl, Br, CF3, NO2, CN, alkyl, O-C1-8 alkyl, C1- alkoxy 4-C1-4alkyl, C0-8-aryl alkylene, oxo, CO (R71), CON (R72) (R73), hydroxy, hydroxy-C1-4alkyl, COO (R74), N (R75) C1-Calkyl 6, N (R76) (R77), SO2CH3 or SCF3; R71, R72, R73, R74, R75, R76, R77 mean independently of each other and optionally together with the nitrogen atom to which they are attached, a ring of 5-6 links that, in addition to the nitrogen atom, can still contain 0-1 additional heteroatoms of the N- C1-6 alkyl, oxygen and sulfur group; or E, K and R11 together form a tricycle, the rings may be, independently of one another, saturated, partially saturated or unsaturated, and may in each case contain 3-8 atoms in the ring; their N-oxides and their physiologically tolerable salts.

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