AR044507A1 - QUINOLINE AND QUINOXALINE COMPOUNDS - Google Patents

QUINOLINE AND QUINOXALINE COMPOUNDS

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Publication number
AR044507A1
AR044507A1 ARP040101024A ARP040101024A AR044507A1 AR 044507 A1 AR044507 A1 AR 044507A1 AR P040101024 A ARP040101024 A AR P040101024A AR P040101024 A ARP040101024 A AR P040101024A AR 044507 A1 AR044507 A1 AR 044507A1
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Argentina
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substituted
carbon
optionally
nitrogen
optionally mono
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Spanish (es)
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Pfizer Prod Inc
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    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
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    • C07D401/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
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Abstract

Compuestos de quinolina y quinoxalina, composiciones farmacéuticas que contienen tales compuestos y el uso de tales compuestos para aumentar ciertos niveles de lípidos en el plasma, incluyendo la lipoproteína de alta densidad del colesterol y para reducir otros niveles de lípidos en el plasma, tales como colesterol LDL y triglicéridos, y por consiguiente, para tratar enfermedades que se ven afectadas por los niveles bajos de colesterol HDL y/o niveles altos de colesterol LDL y triglicéridos, tales como ateroesclerosis y enfermedades cardiovasculares Reivindicación 1: Un compuesto de acuerdo con la fórmula (1) donde C3 es carbono; J es nitrógeno o carbono, donde si J es carbono, entonces el enlace entre C3 y J es un enlace sencillo o doble y si J es nitrógeno, entonces el enlace entre C3 y J es un enlace sencillo; R1 es Y, W-X o W-Y1; donde W es un carbonilo, tiocarbonilo, sulfinilo o sulfonilo; X es -O-Y, -S-Y, -N(H)-Y o -N-(Y)2; Y para cada caso es independientemente Z o una cadena carbonada totalmente saturada, parcialmente insaturada o totalmente insaturada de uno a diez miembros, lineal o ramificada donde cada carbono, distinto del carbono de unión, puede reemplazarse opcionalmente con uno o dos heteroátomos seleccionados independientemente entre oxígeno, azufre y nitrógeno y donde dicho carbono está opcionalmente mono-, di- o tri-substituido independientemente con halo, estando dicho carbono opcionalmente mono-substituido con hidroxi, estando dicho carbono opcionalmente substituido con oxo, estando dicho azufre opcionalmente mono- o di-substituido con oxo, estando dicho nitrógeno opcionalmente mono-, o di-substituido con oxo, y estando dicha cadena carbonada opcionalmente mono-substituida con Z; e Y1 para cada caso es independientemente Z o una cadena carbonada totalmente saturada, parcialmente insaturada o totalmente insaturada de uno a diez miembros, lineal o ramificada, donde cada carbono, distinto del carbono de unión, puede reemplazarse opcionalmente con uno o dos heteroátomos seleccionados independientemente entre oxígeno, azufre y nitrógeno y donde dicho carbono está opcionalmente mono-, di- o tri-substituido independientemente con halo, estando dicho carbono opcionalmente mono-substituido con hidroxi, estando dicho carbono opcionalmente mono-substituido con oxo, estando dicho azufre opcionalmente mono- o di-substituido con oxo, estando dicho nitrógeno opcionalmente mono-, o di-substituido con oxo, y estando dicha cadena carbonada opcionalmente mono-substituida con Z; donde Z es un anillo de tres a ocho miembros, parcialmente saturado, totalmente saturado o totalmente insaturado, que tiene opcionalmente de uno a cuatro heteroátomos seleccionados independientemente entre oxígeno, azufre y nitrógeno, o un anillo bicíclico que consta de dos anillos condensados de tres a seis miembros, parcialmente saturados, totalmente saturados o totalmente insaturados, tomados independientemente, que tienen opcionalmente de uno a cuatro heteroátomos seleccionados independientemente entre oxígeno, azufre y nitrógeno; y dicho substituyente Z está opcionalmente mono-, di- o tri-substituido independientemente con halo, alquenilo C2-6, alquilo C1-6, hidroxi, alcoxi C1-6, alquiltio C1-4, amino, nitro, ciano, oxo, carboxi, alquiloxicarbonilo C1-6, mono-N- o di-N,N-alquilamino C1-6 donde dicho substituyente alquilo C1-6 está opcionalmente mono-, di- o tri-substituido independientemente con halo, hidroxi, alcoxi C1-6, alquiltio C1-4, amino, nitro, ciano, oxo, carboxi, alquiloxicarbonilo C1-6, mono-N- o di-N,N-alquilamino C1-6, estando dicho substituyente alquilo C1-6 o alcoxi C1-6 opcionalmente substituido con uno a nueve átomos de flúor; R2 es una cadena carbonada, parcialmente saturada, totalmente saturada o totalmente insaturada de uno a seis miembros, lineal o ramificada, donde cada carbono, distinto del carbono de unión, puede reemplazarse opcionalmente con uno o dos heteroátomos seleccionados independientemente entre oxígeno y azufre, y donde dicho carbono está opcionalmente mono-, di- o tri-substituido independientemente con halo, estando dicha cadena carbonada opcionalmente mono-substituida con oxo, estando dicho carbono opcionalmente mono-substituido con hidroxi, estando dicho azufre opcionalmente mono- o di-substituido con oxo; o dicho R2 es un anillo parcialmente saturado, totalmente saturado o totalmente insaturado de tres a siete miembros, que tiene opcionalmente de uno a dos heteroátomos seleccionados independientemente entre oxígeno y azufre, donde dicho anillo R2 está opcionalmente unido mediante un alquilo C1-4; donde dicho anillo R2 está opcionalmente mono-, di- o tri-substituido independientemente con halo, alquenilo C2-6, alquilo C1-6, hidroxi, alcoxi C1-6, alquiltio C1-4, amino, nitro, ciano, oxo, carboxi, alquiloxicarbonilo, mono-N- o di-N,N-alquilamino C1-6 donde dicho substituyente alquilo C1-6 está opcionalmente mono- , di- o tri-substituido independientemente con halo, hidroxi, alcoxi C1-6, alquiltio C1-4, oxo o alquiloxicarbonilo C1-6; R3 es una cadena carbonada totalmente saturada, parcialmente insaturada o totalmente insaturada uno a seis miembros, lineal o ramificada, que contiene C4a, donde C4a es un átomo de carbono que conecta con J, donde cada carbono en la cadena carbonada puede reemplazarse opcionalmente con un heteroátomo seleccionado entre oxígeno, azufre y nitrógeno, y donde dicho carbono está opcionalmente mono-, di- o tri-substituido con halo, estando dicho carbono opcionalmente mono-substituido con hidroxi, estando dicho carbono opcionalmente mono-substituido con oxo o nitrógeno, estando dicho azufre opcionalmente mono- o di- substituido con oxo, estando dicho nitrógeno opcionalmente mono- o di-substituido con hidrógeno u oxo, y estando dicha cadena carbonada mono, di-, o tri-substituida con V en C4a o en el carbono R3 adyacente a C4a; siempre que en R3, cuando J es carbono, sea distinto de C4a que está opcionalmente reemplazado con un heteroátomo; y siempre que en R3, cuando J es nitrógeno, sea distinto de C4a que está opcionalmente reemplazado con un heteroátomo y sea distinto de C4a que está opcionalmente mono-substituido con hidroxi o nitrógeno; donde V es un anillo parcialmente saturado, totalmente saturado o totalmente insaturado de tres a ocho miembros, que tiene opcionalmente de uno a cuatro heteroátomos seleccionados independientemente entre oxígeno, azufre y nitrógeno tal que V no es imidazolilo o un anillo heterocíclico totalmente saturado que contiene nitrógeno donde el nitrógeno del anillo está unido al grupo R3; un anillo bicíclico que consta de dos anillos condensados de tres a seis miembros, parcialmente saturados, totalmente saturados o totalmente insaturados, tomados independientemente, que tienen opcionalmente de uno a cuatro heteroátomos seleccionados independientemente entre oxígeno, azufre y nitrógeno; o un anillo tricíclico que consiste de tres anillos condensados de tres a seis miembros, parcialmente saturados, totalmente saturados o totalmente insaturados, tomados independientemente, que tienen opcionalmente de uno a cuatro heteroátomos seleccionados independientemente entre oxígeno, azufre y nitrógeno; y dicho substituyente V está opcionalmente mono-, di-, tri-, tetra- o penta-substituido independientemente con V1, alquil C1-6-V1, C(O)-V1, O-alquil C0-6-V1, alquil C1-6-O-V1, C(O)-mono-N- o di- N,N-alquil C1-6-V1, halo, alquilo C1-6, alquenilo C2-6, hidroxi, alcoxi C1-6, alquiltio C1-4, alquilsulfinilo C1-4, alquilsulfonilo C1-4, mono-N- o di-N,N-alquilsulfonilo C1-6, amino, nitro, ciano, oxo, carboxamoilo, mono-N- o di-N,N- alquilcarboxamoilo C1-6, carboxi, alquiloxicarbonilo C1-6, mono-N- o di-N,N-alquilamino C1-6, donde dicho substituyente alquilo C1-6 o alquenilo C2-6 está opcionalmente mono-, di- o tri-substituido independientemente con hidroxi, alcoxi C1-6, alquiltio C1-4, amino, nitro, ciano, oxo, carboxi, alquiloxicarbonilo C1-6, mono-N- o di-N,N-alquilamino C1-6, donde cada uno de los substituyentes alquilo C1-6, alcoxi C1-6, alquiltio C1-4, alquilsulfonilo C1-4 o alquenilo C2-6 también están opcionalmente substituidos con uno a nueve átomos de flúor; donde V1 es un anillo de tres a seis miembros, parcialmente saturado, totalmente saturado o totalmente insaturado, que tiene opcionalmente de uno a dos heteroátomos seleccionados independientemente entre oxígeno, azufre y nitrógeno, o un anillo bicíclico que consta de dos anillos condensados de tres a seis miembros, parcialmente saturados, totalmente saturados o totalmente insaturados, tomados independientemente, que tienen opcionalmente de uno a cuatro heteroátomos seleccionados independientemente entre oxígeno, azufre y nitrógeno; y dicho substituyente V1 está opcionalmente mono-, di-, tri-, tetra- o penta-substituido independientemente con halo, alquilo C1-6, alcoxi C1-6, hidroxi, oxo, amino, nitro, ciano, alquiloxicarbonilo C1-6, mono-N- o di-N,N-alquilamino C1-6 donde dicho substituyente alquilo C1-6 está opcionalmente mono-substituido con oxo, dicho substituyente alquilo C1-6 o alcoxi C1-6 también están opcionalmente substituidos con uno a nueve átomos de flúor; y cada uno de R4, R5, R6 y R7 es independientemente hidrógeno, un enlace, nitro o halo donde dicho enlace está substituido con T o una cadena carbonada, parcialmente saturada, totalmente saturada o totalmente insaturada (C1-12), lineal o ramificada donde cada carbono puede reemplazarse opcionalmente con uno o dos heteroátomos por cadena carbonada donde los heteroátomos se seleccionan independientemente entre oxígeno, azufre y nitrógeno, donde dicho carbono está opcionalmente mono-, di- o tri-substituido independientemente con halo, estando dicho carbono opcionalmente mono-substituido con hidroxi, estando dicho carbono opcionalmente mono-substituido con oxo o nitrógeno, estando dicho azufre opcionalmente mono- o di-substituido con oxo, estando dicho nitrógeno opcionalmente mono- o di-substituido con hidrógeno u oxo, y estando dicha cadena Quinoline and quinoxaline compounds, pharmaceutical compositions containing such compounds and the use of such compounds to increase certain levels of lipids in the plasma, including high-density lipoprotein of cholesterol and to reduce other levels of lipids in the plasma, such as cholesterol LDL and triglycerides, and therefore, to treat diseases that are affected by low levels of HDL cholesterol and / or high levels of LDL cholesterol and triglycerides, such as atherosclerosis and cardiovascular diseases Claim 1: A compound according to the formula ( 1) where C3 is carbon; J is nitrogen or carbon, where if J is carbon, then the bond between C3 and J is a single or double bond and if J is nitrogen, then the bond between C3 and J is a single bond; R1 is Y, W-X or W-Y1; where W is a carbonyl, thiocarbonyl, sulfinyl or sulfonyl; X is -O-Y, -S-Y, -N (H) -Y or -N- (Y) 2; And for each case it is independently Z or a fully saturated, partially unsaturated or fully unsaturated carbon chain of one to ten members, linear or branched where each carbon, other than the binding carbon, can optionally be replaced with one or two heteroatoms independently selected from oxygen , sulfur and nitrogen and wherein said carbon is optionally mono-, di- or tri-substituted independently with halo, said carbon being optionally mono-substituted with hydroxy, said carbon being optionally substituted with oxo, said sulfur being optionally mono- or di- substituted with oxo, said nitrogen being optionally mono-, or di-substituted with oxo, and said carbon chain being optionally mono-substituted with Z; and Y1 for each case is independently Z or a fully saturated, partially unsaturated or fully unsaturated carbon chain of one to ten members, linear or branched, where each carbon, other than the binding carbon, can optionally be replaced with one or two independently selected heteroatoms between oxygen, sulfur and nitrogen and wherein said carbon is optionally mono-, di- or tri-substituted independently with halo, said carbon being optionally mono-substituted with hydroxy, said carbon being optionally mono-substituted with oxo, said sulfur being optionally mono - or di-substituted with oxo, said nitrogen being optionally mono-, or di-substituted with oxo, and said carbon chain being optionally mono-substituted with Z; where Z is a three to eight member ring, partially saturated, fully saturated or totally unsaturated, which optionally has one to four heteroatoms independently selected from oxygen, sulfur and nitrogen, or a bicyclic ring consisting of two condensed rings of three to six members, partially saturated, fully saturated or totally unsaturated, taken independently, optionally having one to four heteroatoms independently selected from oxygen, sulfur and nitrogen; and said substituent Z is optionally mono-, di- or tri-substituted independently with halo, C2-6 alkenyl, C1-6 alkyl, hydroxy, C1-6 alkoxy, C1-4 alkylthio, amino, nitro, cyano, oxo, carboxy , C1-6 alkyloxycarbonyl, mono-N- or di-N, N-C1-6 alkylamino where said C1-6 alkyl substituent is optionally mono-, di- or tri-substituted independently with halo, hydroxy, C1-6 alkoxy, C1-4 alkylthio, amino, nitro, cyano, oxo, carboxy, C1-6 alkyloxycarbonyl, mono-N- or di-N, N- C1-6 alkylamino, said substituent being C1-6 alkyl or C1-6 alkoxy optionally substituted with one to nine fluorine atoms; R2 is a carbon chain, partially saturated, fully saturated or totally unsaturated with one to six members, linear or branched, where each carbon, other than the binding carbon, can be optionally replaced with one or two heteroatoms independently selected from oxygen and sulfur, and wherein said carbon is optionally mono-, di- or tri-substituted independently with halo, said carbon chain being optionally mono-substituted with oxo, said carbon being optionally mono-substituted with hydroxy, said sulfur being optionally mono- or di-substituted with oxo; or said R2 is a partially saturated, fully saturated or totally unsaturated ring of three to seven members, optionally having one to two heteroatoms independently selected from oxygen and sulfur, wherein said ring R2 is optionally linked by a C1-4 alkyl; wherein said R2 ring is optionally mono-, di- or tri-substituted independently with halo, C2-6 alkenyl, C1-6 alkyl, hydroxy, C1-6 alkoxy, C1-4 alkylthio, amino, nitro, cyano, oxo, carboxy , alkyloxycarbonyl, mono-N- or di-N, N-C1-6 alkylamino where said C1-6 alkyl substituent is optionally mono-, di- or tri-substituted independently with halo, hydroxy, C1-6 alkoxy, C1- alkylthio 4, oxo or C 1-6 alkyloxycarbonyl; R3 is a fully saturated, partially unsaturated or fully unsaturated, one or six-membered, linear or branched carbon chain containing C4a, where C4a is a carbon atom that connects with J, where each carbon in the carbon chain can optionally be replaced with a heteroatom selected from oxygen, sulfur and nitrogen, and wherein said carbon is optionally mono-, di- or tri-substituted with halo, said carbon being optionally mono-substituted with hydroxy, said carbon being optionally mono-substituted with oxo or nitrogen, being said sulfur optionally mono- or di-substituted with oxo, said nitrogen being optionally mono- or di-substituted with hydrogen or oxo, and said carbon chain being mono, di-, or tri-substituted with V at C4a or carbon R3 adjacent to C4a; provided that in R3, when J is carbon, it is different from C4a which is optionally replaced with a heteroatom; and provided that in R3, when J is nitrogen, it is different from C4a which is optionally replaced with a heteroatom and is different from C4a which is optionally mono-substituted with hydroxy or nitrogen; where V is a partially saturated, fully saturated or fully unsaturated ring of three to eight members, optionally having one to four heteroatoms independently selected from oxygen, sulfur and nitrogen such that V is not imidazolyl or a fully saturated nitrogen-containing heterocyclic ring where the ring nitrogen is attached to the R3 group; a bicyclic ring consisting of two condensed rings of three to six members, partially saturated, fully saturated or fully unsaturated, taken independently, which optionally have one to four heteroatoms independently selected from oxygen, sulfur and nitrogen; or a tricyclic ring consisting of three condensed rings of three to six members, partially saturated, fully saturated or fully unsaturated, taken independently, which optionally have one to four heteroatoms independently selected from oxygen, sulfur and nitrogen; and said substituent V is optionally mono-, di-, tri-, tetra- or penta-independently substituted with V1, C1-6-V1 alkyl, C (O) -V1, O-C0-6-V1 alkyl, C1 alkyl -6-O-V1, C (O) -mono-N- or di- N, N-C1-6-V1 alkyl, halo, C1-6 alkyl, C2-6 alkenyl, hydroxy, C1-6 alkoxy, alkylthio C1-4, C1-4 alkylsulfinyl, C1-4 alkylsulfonyl, mono-N- or di-N, N- C 1-6 alkylsulfonyl, amino, nitro, cyano, oxo, carboxamoyl, mono-N- or di-N, N - C1-6 alkylcarboxamoyl, carboxy, C1-6 alkyloxycarbonyl, mono-N- or di-N, N- C1-6 alkylamino, wherein said C1-6 alkyl or C2-6 alkenyl substituent is optionally mono-, di- or tri -substituted independently with hydroxy, C1-6 alkoxy, C1-4 alkylthio, amino, nitro, cyano, oxo, carboxy, C1-6 alkyloxycarbonyl, mono-N- or di-N, N- C1-6 alkylamino, where each of the substituents C1-6 alkyl, C1-6 alkoxy, C1-4 alkylthio, C1-4 alkylsulfonyl or C2-6 alkenyl are also optionally substituted with one to nine fluorine atoms; where V1 is a three to six-membered ring, partially saturated, fully saturated or totally unsaturated, which optionally has one to two heteroatoms independently selected from oxygen, sulfur and nitrogen, or a bicyclic ring consisting of two condensed rings of three to six members, partially saturated, fully saturated or totally unsaturated, taken independently, optionally having one to four heteroatoms independently selected from oxygen, sulfur and nitrogen; and said substituent V1 is optionally mono-, di-, tri-, tetra- or penta-substituted independently with halo, C1-6 alkyl, C1-6 alkoxy, hydroxy, oxo, amino, nitro, cyano, C1-6 alkyloxycarbonyl, mono-N- or di-N, N-C1-6 alkylamino where said C1-6 alkyl substituent is optionally mono-substituted with oxo, said C1-6 alkyl or C1-6 alkoxy substituent are also optionally substituted with one to nine atoms of fluorine; and each of R4, R5, R6 and R7 is independently hydrogen, a bond, nitro or halo where said bond is substituted with T or a carbon chain, partially saturated, fully saturated or fully unsaturated (C1-12), linear or branched wherein each carbon can optionally be replaced with one or two heteroatoms per carbon chain where the heteroatoms are independently selected from oxygen, sulfur and nitrogen, wherein said carbon is optionally mono-, di- or tri-substituted independently with halo, said carbon being optionally mono -substituted with hydroxy, said carbon being optionally mono-substituted with oxo or nitrogen, said sulfur being optionally mono- or di-substituted with oxo, said nitrogen being optionally mono- or di-substituted with hydrogen or oxo, and said chain being

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