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AR034257A1 - Compuesto ureido, composicion farmaceutica que lo comprende y metodo para modular la actividad del receptor de quimiocinas - Google Patents

Compuesto ureido, composicion farmaceutica que lo comprende y metodo para modular la actividad del receptor de quimiocinas

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Publication number
AR034257A1
AR034257A1 ARP010103133A ARP010103133A AR034257A1 AR 034257 A1 AR034257 A1 AR 034257A1 AR P010103133 A ARP010103133 A AR P010103133A AR P010103133 A ARP010103133 A AR P010103133A AR 034257 A1 AR034257 A1 AR 034257A1
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Argentina
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alkyl
groups
substituted
cycloalkyl
chr
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ARP010103133A
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Du Pont Pharm Co
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    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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    • A—HUMAN NECESSITIES
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    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
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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
    • C07D211/36—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 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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    • C07D211/36—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 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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    • 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
    • C07D211/36—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 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
    • C07D211/60—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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    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • 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
    • C07D211/36—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 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
    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
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    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
    • C07D211/96—Sulfur atom
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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    • C07—ORGANIC CHEMISTRY
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    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

Un compuesto ureído de la fórmula (1) o estereoisómeros o sales farmacéuticamente aceptables del mismo, en donde: M está ausente o puede ser CH2, CHR5, CHR13, CR13R13 y CR5R13; Q puede ser CH2, CHR5, CHR13, CR13R13 y CR5R13; J y K, independientemente, pueden ser CH2, CHR5, CHR6, CR6R6 y CR5R6; L puede ser CHR5 y CR5R6; a condición de que: cuando M está ausente, J puede ser CH2, CHR5, CHR13 y CR5R13; Z puede ser O, S, NR1a, C(CN)2, CH(NO2) y CHCN; R1a puede ser H, alquilo C1-6, cicloalquilo C3-6, CONR1bR1b, OR1b, CN, NO2 y (CH2)wfenilo; R1b puede ser H, alquilo C1-3, cicloalquilo C3-6 y fenilo; E es un resto de fórmula (2); G puede ser un enlace, C=O y SO2; el anillo B es un anillo heterocíclico saturado de 5, 6 ó 7 miembros, en donde el anillo heterocíclico incluye radicales -NR9-, -O-, -S(O)p-, -NR9dC(O)-, -C(O)NR9d-, -C(O)O-, -OC(O)-, -NR9dC(O)NR9d-, -NR9dC(O)O-, -NR9dS(O)2-, -S(O)2NR9d- ó -OC(O)NR9d-, en donde el anillo heterocíclico opcionalmente está sustituido con 0 a 2 grupos R8; R1 y R2, independientemente, pueden ser H, alquilo C1-8, alquenilo C3-8, alquinilo C3-8 y (CH2)r-cicloalquilo C3-6; R3 puede ser metilo sustituido con 0-1 grupos R10, alquilo C2-8 sustituido con 0-3 grupos R7, alquenilo C3-8 sustituido con 0-3 grupos R7, alquinilo C3-8 sustituido con 0-3 grupos R7, fluoroalquilo C2, haloalquilo C3-8, un residuo (CR3'R3'')r-carboxíclico C3-8 con 0-5 grupos R15 y un sistema (CR3'R3'')r-heterocíclico de 5-10 miembros que contiene de 1-4 heteroátomos que pueden ser N, O y S, sustituido con 0-3 grupos R15; R3' y R3'', en cada ocasión, pueden ser H, alquilo C1-6, (CH2)r-cicloalquilo C3-6 y fenilo; R4 está ausente, se puede considerar junto con el nitrógeno al cual está unido para formar un N-óxido, o puede ser alquilo C1-8, alquenilo C3-8, alquinilo C3-8, (CH2)r-cicloalquilo C3-6, (CH2)qC(O)R4b, (CH2)qC(O)NR4aR4a', (CH2)qC(O)OR4b y un residuo (CH2)r-carbocíclico C3-10 sustituido con 0-3 grupos R4c; R4a y R4a', en cada ocasión, pueden ser H, alquilo C1-6, (CH2)r-cicloalquilo C3-6 y fenilo; R4b, en cada caso, puede ser alquilo C1-6, alquenilo C3-8, (CH2)r-cicloalquilo C3-6, alquinilo C3-8 y fenilo; R4c, en cada ocasión, puede ser alquilo C1-6, alquenilo C2-8, alquinilo C2-8, cicloalquilo C3-6, Cl, F, Br, I, CN, NO2, (CF2)rCF3, (CH2)rO-alquilo C1-5, (CH2)rOH, (CH2)r-S-alquilo C1-5, (CH2)rNR4aR4a' y (CH2)rfenilo; R5 puede ser un residuo (CR5'R5'')t-carboxíclico C3-10 sustituido con 0-5 grupos R16 y un sistema (CR5'R5'')t-heterocíclico de 5-10 miembros que contiene de 1-5 heteroátomos que pueden ser N, O y S, sustituido con 0-3 grupos R16; R5' y R5'', en cada ocasión, pueden ser H, alquilo C1-6, (CH2)r-cicloalquilo C3-6 y fenilo; R6 puede ser alquilo C1-6, alquenilo C2-8, alquinilo C2-8, (CH2)r-cicloalquilo C3-6, (CF2)rCF3, CN, (CH2)rNR6aR6a', (CH2)rOH, (CH2)rOR6b, (CH2)rSH, (CH2)rSR6b, (CH2)rC(O)OH, (CH2)rC(O)R6b, (CH2)rC(O)NR6aR6a', (CH2)rNR6dC(O)R6a, (CH2)rC(O)OR6b, (CH2)rOC(O)R6b, (CH2)rS(O)pR6b, (CH2)rS(O)2NR6aR6a', (CH2)rNR6dS(O)2R6b y (CH2)t-fenilo sustituido con 0-3 grupos R6c; R6a y R6a' pueden ser H, alquilo C1-6, cicloalquilo C3-6 y fenilo sustituido con 0-3 grupos R6c; R6b puede ser alquilo C1-6, cicloalquilo C3-6 y fenilo sustituido con 0-3 grupos R6c; R6c puede ser alquilo C1-6, cicloalquilo C3-6, Cl, F, Br, I, CN, NO2, (CF2)rCF3, (CH2)rO-alquilo C1-5, (CH2)rOH, (CH2)rS-alquilo C1-5 y (CH2)rNR6dR6d; R6d puede ser H, alquilo C1-6 y cicloalquilo C3-6; a condición de que cuando cualquiera entre J ó K sea CR6R6 y R6 es un grupo ciano o está enlazado al carbono al cual se une a través de un heteroátomo, el otro R6 no es un grupo ciano ni está enlazado al carbono al cual se une a través de un heteroátomo; R7 puede ser NO2, CN, NR7aR7a', OH, OR7d, C(O)H, C(O)OH, C(O)R7b, C(O)NR7aR7a', NR7fC(O)OR7d, OC(O)NR7aR7a', NR7fC(O)R7b, NR7fC(O)NR7fR7f, C(O)OR7d, OC(O)R7b, C(=NR7f)NR7aR7a', NHC(=NR7f)NR7fR7f, S(O)pR7b, S(O)2NR7aR7a', NR7fS(O)2R7b y haloalquilo C1-6; R7a y R7a' pueden ser H, alquilo C1-6, alquenilo C3-8, alquinilo C3-8, un residuo (CH2)r-carbocíclico C3-10 sustituido con 0-5 grupos R7e y un sistema (CH2)r-heterocíclico de 5-10 miembros que contiene de 1-4 heteroátomos seleccionados de N, O y S, sustituido con 0-2 grupos R7e; alternativamente, R7a y R7a', junto con el átomo de N al cual están enlazados, juntos forman un sistema heterocíclico de 5-6 miembros que contiene de 1-2 heteroátomos que pueden ser NR7b, O y S, y opcionalmente está fusionado con un anillo bencénico o un heterociclo aromático de 6 miembros; R7b puede ser H, alquilo C1-6, alquenilo C3-8, alquinilo C3-8, un residuo (CH2)r-carbocíclico C3-6 sustituido con 0-3 grupos R7e, y un sistema (CH2)r-heterocíclico de 5-6 miembros que contiene de 1-4 heteroátomos seleccionados de N, O y S, sustituido con 0-2 grupos R7e; R7d puede ser alquenilo C3-8, alquinilo C3-8, metilo, CF3, alquilo C2-6 sustituido con 0-3 grupos R7e, un residuo (CH2)r-carbocíclico C3-10 sustituido con 0-3 grupos R7e y un sistema (CH2)r-heterocíclico de 5-6 miembros que contiene de 1-4 heteroátomos que pueden ser N, O y S, sustituido con 0-3 grupos R7e; R7e, en cada ocasión, puede ser alquilo C1-6, alquenilo C2-8, alquinilo C2-8, (CH2)r-cicloalquilo C3-6, C(O)-alquilo C1-6, C(O)O-alquilo C1-6, Cl, F, Br, I, CN, NO2, (CF2)CF3, (CH2)rO-alquilo C1-5, OH, SH, (CH2)rS-alquilo C1-5, (CH2)rNR7fR7f, (CH2)r-fenilo y un heterociclo sustituido con 0-1 grupos R7g, en donde el heterociclo puede ser imidazol, tiazol, oxazol, pirazol, 1,2,4-triazol, 1,2,3-triazol, isoxazol y tetrazol; R7f puede ser H, alquilo C1-6, cicloalquilo C3-6 y fenilo; R7g puede ser metilo, etilo, acetilo y CF3; R7h puede ser H, alquilo C1-6, cicloalquilo C3-6, (CH2)r-fenilo, C(O)R7f, C(O)OR7i y SO2R7i; R7i puede ser alquilo C1-6 o cicloalquilo C3-6; R8 puede ser alquilo C1-6, alquenilo C2-8, alquinilo C2-8, haloalquilo C1-6, un residuo (CH2)r-carbocíclico C3-10 sustituido con 0-3 grupos R8c y un sistema (CH2)r-heterocíclico de 5-10 miembros que contiene de 1-4 heteroátomos seleccionados de N, O y S, sustituido con 0-2 grupos R8c; R8a puede ser H, alquilo C1-6, alquenilo C2-8, alquinilo C2-8, un residuo (CH2)r-carbocíclico C3-10 sustituido con 0-5 grupos R8e y un sistema (CH2)r-heterocíclico de 5-10 miembros que contiene de 1-4 heteroátomos que pueden ser N, O y S, sustituido con 0-3 grupos R8e; R8b puede ser alquilo C1-6, alquenilo C3-8, alquinilo C3-8, un residuo (CH2)r-carbocíclico C3-6 sustituido con 0-2 grupos R8e y un sistema (CH2)r-heterocíclico de 5-6 miembros que contiene 1-4 heteroátomos seleccionados de N, O y S, sustituido con 0-3 grupos R8e; R8c puede ser alquilo C1-6, alquenilo C2-8, alquinilo C2-8, (CH2)r-cicloalquilo C3-6, Cl, Br, I, F, (CF2)CF3, NO2, CN, (CH2)rNR8fR8f, (CH2)rOH, (CH2)rO-alquilo C1-4, (CH2)rS-alquilo C1-4, (CH2)rC(O)OH, (CH2)rC(O)R8a, (CH2)rC(O)NR8fR8f, (CH2)rNR8fC(O)R8a, (CH2)rC(O)O-alquilo C1-4, (CH2)rOC(O)R8b, (CH2)rS(O)pR8b, (CH2)rS(O)2NR8fR8f, (CH2)rNR8fS(O)2R8b y (CH2)r-fenilo sustituido con 0-3 grupos R8e; R8e puede ser alquilo C1-6, alquenilo C2-8, alquinilo C2-8, cicloalquilo C3-6, Cl, F, BR, I, CN, NO2, (CF2)CF3, (CH2)rO-alquilo C1-5, (CH2)rOH, (CH2)rSH, (CH2)rS-alquilo C1-5, (CH2)rNR8fR8f y (CH2)r-fenilo; R8f puede ser H, alquilo C1-6 y cicloalquilo C3-6; R9 es H, CH3, alquilo C2-6 sustituido con 0-3 grupos R9a, alquenilo C3-8, alquinilo C3-8, haloalquilo C1-6, (CHR')rC(O)-alquilo C1-6 sustituido con 0-3 grupos R9j, (CHR')rC(O)O-alquilo C1-6 sustituido con 0-3 grupos R9b, (CHR')rC(O)NR9dR9d', (CHR')rS(O)2-alquilo C1-6, S(O)2-haloalquilo C1-6, (CHR')rS(O)2NR9dR9d, R9', (CHR')rC(O)R9', (CHR')rC(O)NR9dR9', (CHR')rS(O)2R9' y (CHR')rS(O)2NR9dR9'; R9', en cada ocasión, es (CHR')r-cicloalquilo C3-6 sustituido con 0-3 grupos R9e, (CHR')r-fenilo sustituido con 0-3 grupos R9c, un sistema (CHR')r-heterocíclico de 5-10 miembros que contiene 1 a 4 heteroátomos que se seleccionan de N, O y S, sustituido con 0-3 grupos R9c; R9a, puede ser CN, NO2, O-alquilo C1-5, CF3, OH, OC(O)-alquilo C1-5, S-alquilo C1-5, S(O)p-alquilo C1-5 y NR9dR9d'; R9b, puede ser cicloalquilo C3-6, CN, (CF2)rCF3, (CH2)qO-alquilo C1-5, (CH2)qOH, (CH2)qS-alquilo C1-5, (CH2)rS(O)p-alquilo C1-5 y (CH2)qNR9dR9d'; R9c puede ser alquilo C1-6, cicloalquilo C3-6, Cl, F, Br, I, CN, NO2, (CF2)rCF3, (CH2)rO-alquilo C1-5, (CHR')rC(O)-alquilo C1-5, (CHR')rC(O)O-alquilo C1-5, (CHR')rC(O)NR9dR9d', (CH2)rOH, (CH2)rS-alquilo C1-5, (CH2)rS(O)p-alquilo C1-5 y (CH2)rNR9dR9d'; a condición de que si R9c está unido a un átomo de carbono enlazado con el nitrógeno del anillo B, entonces R9c es (CH2)qOH, (CH2)qO-alquilo C1-5, (CH2)qS-alquilo C1-5, (CH2)qS(O)q-alquilo C1-5 y (CH2)qNR9dR9d'; R9d y R9d' son, en cada ocasión, H, alquilo C1-6, cicloalquilo C3-6 y fenilo; alternativamente, R9d y R9d', junto con el átomo de N al cual están enlazados, juntos forman un sistema heterocíclico de 5-6 miembros que contiene de 1-2 heteroátomos que se seleccionan de NR9h, O, y S, y opcionalmente está fusionado con un anillo bencénico o con un heterociclo aromático de 6 miembros; R9e puede ser alquilo C1-6, cicloalquilo C3-6, Cl, F, Br, I, CN, NO2, (CF2)rCF3, (CH2)rO-alquilo C1-5, (CHR')rC(O)O-alquilo C1-5, (CHR')rC(O)NR9dR9d', (CH2)rOH, (CH2)rS-alquilo C1-5, (CH2)rS(O)p-alquilo C1-5 y (CH2)rNR9dR9d', o, alternativamente, dos grupos R9e en el mismo átomo de C forman un grupo =O; R9h es H, alquilo C1-6, cicloalquilo C3-6, (CH2)r-fenilo, C(O)R9f, C(O)OR9i y SO2R9i; R9i es alquilo C1-6, ó cicloalquilo C3-6; R9j es cicloalquilo C3-6, CN, (CF2)rCF3, (CH2)rO-alquilo C1-5, (CH2)rOH, (CH2)rS-alquilo C1-5, (CH2)rS(O)p-alquilo C1-5 y (CH2)rNR9dR9d'; R10 se selecciona entre C(O)H, C(O)OH, C(O)R10b, C(O)NR10aR10a', C(O)OR10d, C(=NR10f)NR10aR10a', S(O)R10b, S(O)2R10b y S(O)2NR10aR10a'; R10a y R10a', en cada ocasión, son H, alquilo C1-6, alquenilo C3-8, alquinilo C3-8, un residuo (CH2)r-carbocíclico C3-10 sustituido con 0-5 grupos R10e, y un sistema (CH2)r-heterocíclico de 5-10 miembros que contiene de 1-4 heteroátomos que se seleccionan de N, O y S, sustituido
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IL153123A0 (en) 2003-06-24
BR0111878A (pt) 2005-05-24
CA2413245A1 (en) 2002-01-10
US6627629B2 (en) 2003-09-30
JP2004517805A (ja) 2004-06-17
WO2002002525A3 (en) 2002-08-29
MXPA02012712A (es) 2003-04-25
AU2001273129A1 (en) 2002-01-14
WO2002002525A2 (en) 2002-01-10
EP1296978A2 (en) 2003-04-02
CN1440402A (zh) 2003-09-03
HK1054032A1 (zh) 2003-11-14
US6949546B2 (en) 2005-09-27

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