AR030143A1 - 1,4-SUBSTITUTED CYCLOHEXYL COMPOUNDS, USES OF SUCH COMPOUNDS FOR THE MANUFACTURE OF MEDICINES, ISOTOPICALLY LABELED COMPOUNDS, DIAGNOSTIC AGENT, PHARMACEUTICAL COMPOSITIONS, PROCESS FOR THE PREPARATION OF SUCH COMPOSIUMS IN THEIR COMPOSITE USE - Google Patents

1,4-SUBSTITUTED CYCLOHEXYL COMPOUNDS, USES OF SUCH COMPOUNDS FOR THE MANUFACTURE OF MEDICINES, ISOTOPICALLY LABELED COMPOUNDS, DIAGNOSTIC AGENT, PHARMACEUTICAL COMPOSITIONS, PROCESS FOR THE PREPARATION OF SUCH COMPOSIUMS IN THEIR COMPOSITE USE

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AR030143A1
AR030143A1 ARP990102988A ARP990102988A AR030143A1 AR 030143 A1 AR030143 A1 AR 030143A1 AR P990102988 A ARP990102988 A AR P990102988A AR P990102988 A ARP990102988 A AR P990102988A AR 030143 A1 AR030143 A1 AR 030143A1
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optionally
heteroaryl
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Abstract

Compuestos de ciclohexilo 1,4-sustituído que comprenden la formula (1) en donde A es un compuesto de forrmula (2) o (3), en donde R2 y R3 son como se definen más adelante; Z es (CH2) m o un grupo carbonilo; m y n son cada una e independientemente un numero entero de entre 0-3, y uno o más de los hidrogenos en ése tipo de cadena alquileno puede optativamente estar sustituido por cualquiera de alquiloC1-6, alcoxi C1-6, o hidroxi; o uno o más de los grupos metileno pueden estar optativamente sustituidos mediante un heteroátomo como ser O, N o S; m y n pueden no ser ambos 0; Q se selecciona entre cualquiera de CH3; de formula (3) en donde R4, R5 y R6 es cada uno e independientemente seleccionado entre cualquiera de (i) arilo C6-10, o (ii) heteroarilo que tiene entre 5 y 10 átomos y siendo el heteroátomo seleccionado entre cualquiera de S, N y O; y en donde el arilo y heteroarilo pueden ser sustituidos optativa e independientemente por 1 o 2 sustituyentes Y donde cada Y es como se define más adelante; (iii) hidrogeno; (iv) un alquilo C1-6 recto a ramificado, alquenilo C2-6 o alquinilo C2-6; (v) alcoxi C1-3; (vi) cicloalquilo C3-10 saturado o insaturado, optativa e independientemente sustituido por uno o más grupos arilo o grupos heteroarilo que tienen entre 5 y 10 átomos siendo el o los heteroátomos seleccionados entre cualquiera de S, N y O y en donde el arilo y heteroarilo pueden optativa e independientemente estar sustituidos por 1 o 2 sustituyentes Y en donde cada Y es como se define más adelante; (vii) û [(CH2)q-aril] donde q es un numero entero de entre 1 û 3, y el arilo puede ser sustituido optativamente por 1 o 2 sustituyentes Y, donde cada Y es como se define más adelante; (viii) û [(CH2) r û heteroaril ] donde r es un numero entero de entre 1 û 3, y el heteroarilo tiene entre 5 y 10 átomos siendo los heteroátomos seleccionados entre cualquiera de S, N y O, optativa e independientemente sustituidos por 1 o 2 sustituyentes Y como se define más adelante; (ix) û [CH2-O-aril] donde el arilo puede ser sustituido optativamente por 1 o 2 sustituyentes Y, donde cada Y es como se define más adelante; (x) de formula (4) donde q es un numero entero entre 1-3, y el arilo es como se define más adelante, optativamente sustituido por 1 o 2 sustituyentes Y, donde cada Y es como se define más adelante; R1 se selecciona entre cualquiera de (i) un alquilo C1-6 recto o ramificado, alquenilo C2-6 o alquinilo C2-6, donde cada alquilo, alquenilo o alquinilo puede estar sustituido optativamente por uno o más sustituyentes aromáticos o heteroaromáticos; (ii) cicloalquilo C3-7, optativamente comprendiendo una o más insaturaciones y optativamente sustituido por uno de más de alquilo C1-6, alcoxi C1-6, hidroxi; o sustituido por uno o más arilo(s), o heteroarilo(s) que tienen entre 5 y 10 átomos y el o los heteroátomos son seleccionados de cualquiera de S, N y O y en donde el arilo y el heteroarilo pueden ser sustituidos optativa e independientemente por 1 o 2 sustituyentes Y en donde cada Y es como se define más adelante; (iii) hidrogeno, halogeno o alcoxi C1-6; ( iv) arilo C6-10; (v) teniendo el heteroarilo de 5 a 10 átomos y estando el heteroátomo seleccionado entre cualquiera de S, N y O; en donde el arilo y el heteroarilo pueden ser sustituidos optativa e independientemente por 1 o 2 sustituyentes Y en donde cada Y es como se define más adelante (vi) 9,10-dihidro-9,10-etanoantracenilo; (vii) û[(CH2)q-aril] donde q es un numero entero entre 1-3 y el arilo puede optativamente ser sustituido por 1 o 2 sustituyentes Y, donde cada Y es como se define más adelante; (viii) û[(CH2)r-heteroaril] donde r es un numero entero entre 1-3, teniendo el heteroarilo entre 5 y 10 átomos y estando el o los heteroátomos seleccionados entre cualquiera de S, N y O, y en donde el o los heteroátomos puede ser sustituidos optativa e independientemente por 1 o 2 sustituyentes Y, donde cada Y es como se define más adelante;.(ix) û[(CH2)q-aril-O-(CH2)r-aril] donde q y r es cada uno e independientemente un numero entero entre 1-3; (x) û(CH2)q-[cicloalquil C3-6] donde q es entre 1-2, optativamente sustituido por 1 o 2 sustituyentes Y donde cada Y es como se define más adelante; R2 se selecciona entre cualquiera de (i) hidrogeno; (ii) un alquilo C1-6 recto o ramificado, alquenilo C2-6 o alquinilo C2-6 donde cada alquilo, alquenilo o alquinilo puede estar sustituido optativamente por uno o más sustituyentes aromáticos o heteroaromáticos; (iii) arilalquilo C6-10, en donde el arilo puede estar optativamente sustituido por uno o más heteroarilos que tienen entre 5 y 10 átomos y estando el heteroátomo seleccionado entre cualquiera de S, N y O, y en donde el arilo y el heteroarilo pueden estar optativa e independientemente sustituidos por 1 o 2 sustituyentes Y en donde cada Y es como se define más adelante; (iv) heteroaril-(alquilo C5-10), donde el heteroarilo tiene entre 5 y 10 átomos y estando el heteroátomo seleccionado entre cualquiera de S, N y O, y en donde el arilo y heteroarilo pueden estar sustituidos optativa e independientemente por 1 o 2 sustituyentes Y donde cada Y es como se define más abajo; (v) cicloalquilo C3-10 comprendiendo optativamente una o más insaturaciones y optativamente sustituido por uno o más heteroarilos donde el heteroarilo tiene entre 5 y 10 átomos y estando el heteroátomo seleccionado entre cualquiera de S, N y O; y en donde el arilo y heteroarilo pueden estar optativa e independientemente sustituidos por 1 o 2 sustituyentes Y donde cada Y es como se define más abajo; (vi) arilo C6-10 optativa e independientemente sustituido por uno o más heteroarilos que tienen entre 5 y 10 átomos y estando el o los heteroátomos seleccionados entre cualquiera de S, N y O y en donde el heteroarilo puede optativa e independientemente sustituido por 1 o 2 sustituyentes Y donde cada Y es como se define más abajo; (vii) teniendo el heteroarilo entre 5 y 10 átomos y estando el heteroátomo seleccionado entre cualquiera de S, N y O; en donde el arilo y heteroarilo pueden estar sustituidos optativa e independientemente por 1 o 2 sustituyentes Y donde cada Y es como se define más abajo; R3 se selecciona entre cualquiera de (i) hidrogeno; (ii) un alquilo C1-6 recto o ramificado, alquenilo C2-6 o alquinilo C2-6 donde cada alquilo, alquenilo o alquinilo puede estar sustituido optativamente por uno o más sustituyentes aromáticos o heteroaromáticos; (iii) arilalquilo C6-10, en donde el arilo puede optativamente estar sustituido por uno o más heteroarilos que tienen entre 5 y 10 átomos y estando el heteroátomo seleccionado entre cualquiera de S, N y O; y en donde el arilo y el heteroarilo pueden estar optativa e independientemente sustituidos por 1 o 2 sustituyentes Y en donde cada Y es como se define más adelante; (iv) heteroaril-(alquilo C5-10), donde el heteroarilo tiene entre 5 y 10 átomos y estando el heteroátomo seleccionado entre cualquiera de S, N y O, y en donde el arilo y heteroarilo pueden estas sustituidos optativa e independientemente por 1 o 2 sustituyentes Y donde cada Y es como se define más abajo; (v) cicloalquilo C3-10, comprendiendo optativamente una o más insaturaciones y optativamente sustituido por uno o más heteroarilos que tienen entre 5 y 10 átomos y estando el heteroátomo seleccionado entre cualquiera de S, N y O; y en donde el arilo y heteroarilo pueden estar optativa e independientemente sustituidos por 1 o 2 sustituyentes Y donde cada Y es como se define más abajo; (vi) es formula (5) en donde R7, R8, R9, R10 y R11 es cada uno e independientemente seleccionado entre (a) hidrogeno; (b) un alquilo C1-6 recto o ramificado, alquenilo C2-6 o alquinilo C2-6, donde cada alquilo, alquenilo o alquinilo puede estar sustituido optativamente por uno o más sustituyentes aromáticos o heteroaromáticos; (c) arilalquilo C6-10 en donde el arilo puede optativamente estar sustituido por uno o más heteroarilos que tiene entre 5 y 10 átomos y estando el heteroátomo seleccionado entre cualquiera de S, N y O; y en donde el arilo y el heteroarilo pueden estar optativa e independientemente sustituidos por 1 o2 sustituyentes Y en donde cada Y es como se define más adelante; (d) heteroarilo-(alquilo C5-10), donde el heteroarilo tiene entre 5 y 10 átomos y estando el heteroátomo seleccionado entre cualquiera de S, N y O, y en donde el arilo y heteroarilo pueden estar sustituidos optativa e independientemente por 1 o 2 sustituyentes Y donde cada Y es como se define más abajo; (e) cicloalquilo C3-10, comprendiendo optativamente una o más insaturaciones y optativamente sustituido por uno o más heteroarilos donde el heteroarilo tiene entre 5 y 10 átomos y estando el heteroátomo seleccionado entre cualquiera de S, N y O, y en donde el arilo y heteroarilo pueden estar optativa e independientemente sustituidos por 1 o 2 sustituyentes Y donde cada Y es como se define más abajo; (f) arilo C6-10, optativa e independientemente sustituido por uno o más heteroarilos que tienen entre 5 y 10 átomos y estando el o los heteroátomos seleccionados entre cualquiera de S, N y O y en donde el heteroarilo puede optativa e independientemente sustituido por 1 o 2 sustituyentes Y donde cada Y es como se define más abajo; o R2 y R3 pueden formar optativamente un anillo heterocíclico; Y es cada uno e independientemente seleccionado entre cualquiera de hidrogeno, CH3, -(CH2)p1CF3; halogeno; alcoxi C1-3, hidroxi, -NO2; -OCF3; -CONRaRb, -COORa, -CORa, -(CH2)p2NRaRb, -(CH2)p3CH3, (CH2)p4SORaRb, -(CH2)p5SO2Ra, -(CH2)p6SO2NRa, (alquil-cicloalquilo) C4-8 en donde alquilo es alquilo C1-2 y cicloalquilo es cicloalquilo C3-6; 1 o 2 heteroarilos tienen entre 5 y 10 átomos y estando el o los heteroátomos seleccionados entre cualquiera de S, N y O; y oxidos como ser N-oxidos o sulfoxidos; y en donde Ra y Rb es cada uno independientemente seleccionado entre hidrogeno, un alquilo C1-6, alquenilo C1-6 cicloalquilo C3-8 recto o ramificado y en donde p1, p2, p3, p4, p5 y p6 cada uno es independientemente 0, 1 1,4-substituted cyclohexyl compounds comprising formula (1) wherein A is a compound of formula (2) or (3), wherein R2 and R3 are as defined below; Z is (CH2) m or a carbonyl group; m and n are each and independently an integer between 0-3, and one or more of the hydrogens in that type of alkylene chain may optionally be substituted by any of C 1-6 alkyl, C 1-6 alkoxy, or hydroxy; or one or more of the methylene groups may be optionally substituted by a heteroatom such as O, N or S; m and n may not be both 0; Q is selected from any of CH3; of formula (3) wherein R4, R5 and R6 are each and independently selected from any of (i) C6-10 aryl, or (ii) heteroaryl having between 5 and 10 atoms and the heteroatom being selected from any of S , N and O; and wherein the aryl and heteroaryl may be optionally and independently substituted by 1 or 2 substituents Y where each Y is as defined below; (iii) hydrogen; (iv) a straight to branched C1-6 alkyl, C2-6 alkenyl or C2-6 alkynyl; (v) C1-3 alkoxy; (vi) saturated or unsaturated C3-10 cycloalkyl, optionally and independently substituted by one or more aryl groups or heteroaryl groups having between 5 and 10 atoms, the heteroatom (s) being selected from any of S, N and O and wherein the aryl and heteroaryl may optionally and independently be substituted by 1 or 2 substituents Y where each Y is as defined below; (vii) û [(CH2) q-aryl] where q is an integer between 1 û 3, and the aryl can be optionally substituted by 1 or 2 substituents Y, where each Y is as defined below; (viii) û [(CH2) r û heteroaryl] where r is an integer between 1 û 3, and the heteroaryl has between 5 and 10 atoms being the heteroatoms selected from any of S, N and O, optional and independently substituted by 1 or 2 substituents AND as defined below; (ix) û [CH2-O-aryl] where the aryl can be optionally substituted by 1 or 2 substituents Y, where each Y is as defined below; (x) of formula (4) where q is an integer between 1-3, and the aryl is as defined below, optionally substituted by 1 or 2 substituents Y, where each Y is as defined below; R1 is selected from any of (i) a straight or branched C1-6 alkyl, C2-6 alkenyl or C2-6 alkynyl, wherein each alkyl, alkenyl or alkynyl may be optionally substituted by one or more aromatic or heteroaromatic substituents; (ii) C3-7 cycloalkyl, optionally comprising one or more unsaturations and optionally substituted by one of more than C1-6 alkyl, C1-6 alkoxy, hydroxy; or substituted by one or more aryl (s), or heteroaryl (s) having between 5 and 10 atoms and the heteroatom (s) are selected from any of S, N and O and wherein the aryl and heteroaryl can be optionally substituted and independently by 1 or 2 substituents Y where each Y is as defined below; (iii) hydrogen, halogen or C1-6 alkoxy; (iv) C6-10 aryl; (v) having the heteroaryl of 5 to 10 atoms and the heteroatom being selected from any of S, N and O; wherein the aryl and the heteroaryl may be optionally and independently substituted by 1 or 2 Y substituents wherein each Y is as defined below (vi) 9,10-dihydro-9,10-ethanoanthracenyl; (vii) û [(CH2) q-aryl] where q is an integer between 1-3 and the aryl can optionally be substituted by 1 or 2 substituents Y, where each Y is as defined below; (viii) û [(CH2) r-heteroaryl] where r is an integer between 1-3, the heteroaryl having between 5 and 10 atoms and the heteroatom (s) being selected from any of S, N and O, and where the heteroatom (s) may be optionally and independently substituted by 1 or 2 Y substituents, where each Y is as defined below; (ix) û [(CH2) q-aryl-O- (CH2) r-aril] where qyr is each and independently an integer between 1-3; (x) û (CH2) q- [C3-6 cycloalkyl] where q is between 1-2, optionally substituted by 1 or 2 substituents Y where each Y is as defined below; R2 is selected from any of (i) hydrogen; (ii) a straight or branched C1-6 alkyl, C2-6 alkenyl or C2-6 alkynyl wherein each alkyl, alkenyl or alkynyl may be optionally substituted by one or more aromatic or heteroaromatic substituents; (iii) C6-10 arylalkyl, wherein the aryl may be optionally substituted by one or more heteroaryls having between 5 and 10 atoms and the heteroatom being selected from any of S, N and O, and wherein the aryl and heteroaryl they may be optional and independently substituted by 1 or 2 Y substituents where each Y is as defined below; (iv) heteroaryl- (C5-10 alkyl), where the heteroaryl has between 5 and 10 atoms and the heteroatom being selected from any of S, N and O, and wherein the aryl and heteroaryl may be optionally and independently substituted by 1 or 2 substituents Y where each Y is as defined below; (v) C3-10 cycloalkyl optionally comprising one or more unsaturations and optionally substituted by one or more heteroaryls where the heteroaryl has between 5 and 10 atoms and the heteroatom being selected from any of S, N and O; and wherein the aryl and heteroaryl may be optionally and independently substituted by 1 or 2 substituents Y where each Y is as defined below; (vi) C6-10 aryl optional and independently substituted by one or more heteroaryls having between 5 and 10 atoms and the heteroatom (s) being selected from any of S, N and O and wherein the heteroaryl may be optional and independently substituted by 1 or 2 substituents Y where each Y is as defined below; (vii) having the heteroaryl between 5 and 10 atoms and the heteroatom being selected from any of S, N and O; wherein the aryl and heteroaryl may be optionally and independently substituted by 1 or 2 substituents Y where each Y is as defined below; R3 is selected from any of (i) hydrogen; (ii) a straight or branched C1-6 alkyl, C2-6 alkenyl or C2-6 alkynyl wherein each alkyl, alkenyl or alkynyl may be optionally substituted by one or more aromatic or heteroaromatic substituents; (iii) C6-10 arylalkyl, wherein the aryl may optionally be substituted by one or more heteroaryls having between 5 and 10 atoms and the heteroatom being selected from any of S, N and O; and wherein aryl and heteroaryl may be optionally and independently substituted by 1 or 2 substituents Y where each Y is as defined below; (iv) heteroaryl- (C5-10 alkyl), where the heteroaryl has between 5 and 10 atoms and the heteroatom being selected from any of S, N and O, and wherein the aryl and heteroaryl can be optionally and independently substituted by 1 or 2 substituents Y where each Y is as defined below; (v) C3-10 cycloalkyl, optionally comprising one or more unsaturations and optionally substituted by one or more heteroaryls having between 5 and 10 atoms and the heteroatom being selected from any of S, N and O; and wherein the aryl and heteroaryl may be optionally and independently substituted by 1 or 2 substituents Y where each Y is as defined below; (vi) is formula (5) wherein R7, R8, R9, R10 and R11 is each and independently selected from (a) hydrogen; (b) a straight or branched C1-6 alkyl, C2-6 alkenyl or C2-6 alkynyl, wherein each alkyl, alkenyl or alkynyl may be optionally substituted by one or more aromatic or heteroaromatic substituents; (c) C6-10 arylalkyl wherein the aryl may optionally be substituted by one or more heteroaryls having between 5 and 10 atoms and the heteroatom being selected from any of S, N and O; and wherein aryl and heteroaryl may be optionally and independently substituted by 1 or 2 substituents Y where each Y is as defined below; (d) heteroaryl- (C5-10 alkyl), where the heteroaryl has between 5 and 10 atoms and the heteroatom being selected from any of S, N and O, and wherein the aryl and heteroaryl may be optionally and independently substituted by 1 or 2 substituents Y where each Y is as defined below; (e) C3-10 cycloalkyl, optionally comprising one or more unsaturations and optionally substituted by one or more heteroaryls where the heteroaryl has between 5 and 10 atoms and the heteroatom being selected from any of S, N and O, and wherein the aryl and heteroaryl may be optionally and independently substituted by 1 or 2 substituents Y where each Y is as defined below; (f) C6-10 aryl, optionally and independently substituted by one or more heteroaryls having between 5 and 10 atoms and the heteroatom (s) being selected from any of S, N and O and wherein the heteroaryl can be optionally and independently substituted by 1 or 2 substituents Y where each Y is as defined below; or R2 and R3 may optionally form a heterocyclic ring; Y is each and independently selected from any of hydrogen, CH3, - (CH2) p1CF3; halogen; C1-3 alkoxy, hydroxy, -NO2; -OCF3; -CONRaRb, -COORa, -CORa, - (CH2) p2NRaRb, - (CH2) p3CH3, (CH2) p4SORaRb, - (CH2) p5SO2Ra, - (CH2) p6SO2NRa, (alkyl-cycloalkyl) C4-8 where alkyl is C1-2 alkyl and cycloalkyl is C3-6 cycloalkyl; 1 or 2 heteroaryls have between 5 and 10 atoms and the heteroatom (s) being selected from any of S, N and O; and oxides such as N-oxides or sulfoxides; and wherein Ra and Rb are each independently selected from hydrogen, a C1-6 alkyl, C1-6 straight or branched C3-8 cycloalkyl and wherein p1, p2, p3, p4, p5 and p6 each is independently 0 , one

ARP990102988A 1998-06-22 1999-06-22 1,4-SUBSTITUTED CYCLOHEXYL COMPOUNDS, USES OF SUCH COMPOUNDS FOR THE MANUFACTURE OF MEDICINES, ISOTOPICALLY LABELED COMPOUNDS, DIAGNOSTIC AGENT, PHARMACEUTICAL COMPOSITIONS, PROCESS FOR THE PREPARATION OF SUCH COMPOSIUMS IN THEIR COMPOSITE USE AR030143A1 (en)

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