AR048242A1 - 2,3,4,5-tetrahidro-1h-benzo[d]azepinas 6-sustituidas como agonistas del receptor 5-ht2c - Google Patents

2,3,4,5-tetrahidro-1h-benzo[d]azepinas 6-sustituidas como agonistas del receptor 5-ht2c

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AR048242A1
AR048242A1 ARP050100686A ARP050100686A AR048242A1 AR 048242 A1 AR048242 A1 AR 048242A1 AR P050100686 A ARP050100686 A AR P050100686A AR P050100686 A ARP050100686 A AR P050100686A AR 048242 A1 AR048242 A1 AR 048242A1
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alkyl
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Lilly Co Eli
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Abstract

Composicion farmacéutica que los comprende y usos. Un compuesto de formula (1), donde: R1 es hidrogeno, fluoro, o alquilo C1-3; cada R2, R3, y R4 es independientemente hidrogeno, metilo, o etilo; R5 es hidrogeno, fluoro, metilo, o etilo; R6 es - C:::C-R10, -O-R12, -S-R14, o -NR24R25; R7 es hidrogeno, halo, ciano, alquilo C1-6 opcionalmente sustituido con 1 a 6 sustituyentes fluoro, alquenilo C2-6 opcionalmente sustituido con 1 a 6 sustituyentes fluoro, cicloalquilo C3-7, alcoxi C1-6 opcionalmente sustituido con 1 a 6 sustituyentes fluoro, alquiltio C1-6 opcionalmente sustituido con 1 a 6 sustituyentes fluoro, Ph1-alquiloC0-3, Ph1-alquilC0-3-O-, o Ph1-alquilC0-3-S-; R8 es hidrogeno, halo, ciano, o -SCF3; R9 es hidrogeno, halo, ciano, -CF3, -SCF3, o alcoxi C1-3 opcionalmente sustituido con 1 a 6 sustituyentes fluoro, R10 es -CF3, etilo sustituido con 1 a 5 sustituyentes fluoro, alquilo C3-6 opcionalmente sustituido con 1 a 6 sustituyentes fluoro, cicloalquilC3-7-alquiloC0- 3, Ar1-alquiloC0-3, Ph1-alquiloC0-3, o 3-alquilC1-4-2-oxo-imidazolin-1-il-alquiloC1-3; R12 es Ph2-alquiloC1-3, Ar2-alquiloC1-3, alquilC1-6-S-alquiloC2-6, cicloalquilC3-7-S-alquiloC2-6, fenil-S-alquiloC2-6, Ph2-S-alquiloC2-6, fenilcarbonil-alquiloC1- 3, Ph2-C(O)-alquiloC1-3, alcoxiC1-6carbonil-alquiloC3-6, cicloalquilC3-7-OC(O)-alquiloC3-6, feniloxicarbonil-alquiloC3-6, Ph2-OC(O)-alquiloC3-6, Ar2-OC(O)-alquiloC3-6, cicloalquilC3-7-NH-C(O)-alquilC2-4-, Ph1-NH-C(O)-alquilC2-4-, Ar2-NH-C(O)- alquilC2-4-, o o R13-C(O)NH-alquiloC2-4; R13 es cicloalquilC3-7-alquiloC0-3, Ph1, Ar2, o alcoxi C1-3 opcionalmente sustituido con 1 a 6 sustituyentes fluoro, Ph1-NH- o Het1 unido a N; R14 es Ar2 que no está N-unido al átomo de azufre, Ph2, R15-L-, tetrahidrofuranilo, tetrahidropiranilo, o fenil-metilo sustituido en el resto metilo con un sustituyente seleccionado entre el grupo compuesto por n-alquiloC1-3 sustituido con hidroxi, alquiloC1-3-O-n-alquiloC1-2, alquiloC1-3-C(O)-n-alquiloC0-2, y alquiloC1-3-O-C(O)-n-alquiloC0-2; donde cuando R14 es Ph2 o Ar2, donde Ar2 es piridilo, entonces R14 puede esta opcionalmente sustituido también con fenil-CH=CH- o fenil-C:::C-; estando dicho fenil-CH=CH- o fenil-C:::C- opcionalmente sustituido adicionalmente con 1 a 3 sustituyentes independientemente seleccionados entre el grupo compuesto por halo, ciano, -SCF3, alquilo C1-6 opcionalmente sustituido adicionalmente con 1 a 6 sustituyentes fluoro, y alcoxi C1-6 opcionalmente sustituido adicionalmente con 1 a 6 sustituyentes fluoro; y donde cuando Ar2 es piridilo puede estar, como alternativa, opcionalmente sustituido con R28R29N-C(O)-, y opcionalmente sustituido adicionalmente con un sustituyente metilo, -CF3, ciano, o -SCF3, o con 1 a 2 sustituyentes halo; y donde el tetrahidrofuranilo y tetrahidropiranilo pueden estar opcionalmente sustituido con un sustituyente oxo, o con uno o dos grupos independientemente seleccionados entre metilo y -CF3; R15 es -OR16, ciano, -SCF3, Ph2, Ar2, quinolinilo, isoquinolinilo, cinolinilo, quinazolinilo, ftalimido, benzotiofenilo opcionalmente sustituido en la posicion 2 con fenilo o bencilo, benzotiazolilo opcionalmente sustituido en la posicion 2 con fenilo o bencilo, benzotiadiazolilo opcionalmente sustituido con fenilo, 2-oxo-dihidroindol-1-ilo opcionalmente sustituido en la posicion 3 con dimetilo germinal o alquilo C1-6 opcionalmente sustituido adicionalmente con 1 a 6 sustituyentes fluoro, 2-oxo-dihidroindol- 5-ilo opcionalmente sustituido en la posicion 3 con dimetilo germinal o alquilo C1-6 opcionalmente sustituido adicionalmente con 1 a 6 sustituyentes fluoro, 2-oxo-imidazolidin-1-ilo opcionalmente sustituido en la posicion 3 con dimetilo germinal o alquilo C1-6 opcionalmente sustituido adicionalmente con 1 a 6 sustituyentes fluoro, 2-oxo-tetrahidropirimidinilo opcionalmente sustituido en la posicion 3 o 4 con dimetilo germinal o alquilo C1-6 opcionalmente sustituido adicionalmente con 1 a 6 sustituyentes fluoro, 2-oxo-tetrahidroquinolin-1-ilo opcionalmente sustituido en la posicion 3 con dimetilo germinal o alquilo C1-6 opcionalmente sustituido adicionalmente con 1 a 6 sustituyentes fluoro, 2-oxo-dihidrobenzimidazol-1-ilo opcionalmente sustituido en la posicion 3 con dimetilo germinal o alquilo C1-6 opcionalmente sustituido adicionalmente con 1 a 6 sustituyentes fluoro, -NR17R18, -C(O)R22, o un heterociclo saturado seleccionado entre el grupo compuesto por pirrolidinilo, piperidinilo, morfolinilo, y tiomorfolinilo, tetrahidrofuranilo, y tetrahidropiranilo; donde Ph2 y Ar2 cuando Ar2 es piridilo, pueden estar opcionalmente sustituidos también con fenil-CH=CH- o fenil-C:::C-; estando dicho fenil-CH=CH- y fenil-C:::C- opcionalmente sustituidos adicionalmenteen el resto fenilo con 1 a 3 sustituyentes independientemente seleccionados entre el grupo compuesto por halo, ciano, -SCF3, alquilo C1-6 opcionalmente sustituido adicionalmente con 1 a 6 sustituyentes fluoro, y alcoxi C1-6 opcionalmente sustituido adicionalmente con 1 a 6 sustituyentes fluoro; y donde Ar2 puede estar, como alternativa, opcionalmente con un sustituyente seleccionado entre el grupo compuesto por cicloalquilC3-7-alquiloC0-3, Het1-alquiloC0- 3, piridil-alquiloC0-3, y fenil-alquiloC0-3, y opcionalmente sustituido adicionalmente con un sustituyente metilo, -CF3, ciano, o -SCF3, o con 1 a 2 sustituyentes halo; estando dicho piridil-alquiloC0-3 y fenil-alquiloC0-3 opcionalmente sustituido adicionalmente con 1-3 sustituyentes independientemente seleccionados entre halo, -CH3, -OCH3, -CF3, -OCF3, -CN, y -SCF3; y donde cuando Ar2 es piridilo, el piridilo puede estar, como alternativa, opcionalmente sustituido con R28R29N-C(O)-, o alquilC1-6-C(O)- opcionalmente sustituido con 1 a 6 sustituyentes fluoro, y puede estar opcionalmente sustituido adicionalmente con un sustituyente metilo, -CF3, ciano, o -SCF3, o con 1 a 2 sustituyentes halo; y donde cuando Ar2 es tiazolilo, el tiazolilo puede estar, como alternativa, opcionalmente sustituido con cicloalquilC3-7-alquilC0-3-NH-; y donde el pirrolidinilo, piperidinilo, morfolinilo, y tiomorfolinilo está sustituido con oxo- en un átomo de carbono adyacente el átomo de nitrogeno del anillo, o está N-sustituido con un sustituyente seleccionado entre el grupo compuesto por: alquilcarbonilo C1-6, alquilsulfonilo C1-6, cicloalquilC3-7-alquilC0-3-C(O)-, cicloalquilC3-7alquilC0-3-S(O)2-, Ph1-alquilC0-3-C(O)-, y Ph1- alquilC0-3-S(O)2-; y puede estar opcionalmente sustituido adicionalmente con 1 o 2 sustituyentes metilo o -CF3, y cuando está sustituido con oxo, puede estar opcionalmente N-sustituido adicionalmente con un sustituyente seleccionado entre el compuesto por: alquilo C1-6 opcionalmente sustituido adicionalmente con 1 a 6 sustituyentes fluoro, cicloalquilC3-7-alquiloC0-3, y Ph1-alquiloC0-3; y donde el tetrahidrofuranilo y tetrahidropiranilo pueden estar opcionalmente sustituidos con un sustituyente oxo, y/o con uno o dos grupos independientemente seleccionados entre metilo y -CF3; L es alquileno C1-6 ramificado o no ramificado, excepto cuando R15 es -NR17R18 o Ar2 unido a N en 1, en cuyo caso L es alquileno C2-6 ramificado o no ramificado, y cuando L es metileno o etileno, L puede estar opcionalmente sustituido con etano geminal o con 1 a 2 sustituyentes fluoro, y cuando R15 es Ph2, Ar2, o un heterociclo saturado, L puede estar, como alternativa, opcionalmente sustituido con un sustituyente seleccionado entre el grupo compuesto por hidroxi, ciano, -SCF3, alcoxi C1-6 opcionalmente sustituido adicionalmente con 1 a 6 sustituyentes fluoro, alcoxiC1-6-carbonilo opcionalmente sustituido adicionalmente con 1 a 6 sustituyentes fluoro, alquilC1-6-carboniloxi opcionalmente sustituido adicionalmente con 1 a 6 sustituyentes fluoro, cicloalquilC3-7)-alquilC0-3-O-, cicloalquilC3-7-alquilC0-3-O-C(O)-, y cicloalquilC3-7-alquilC0-3-C(O)-O-; R16 es hidrogeno, alquilo C1-6 opcionalmente sustituido con 1 a 6 sustituyentes fluoro, alquilcarbonilo C1-6, cicloalquilC3-7-alquiloC0-3, cicloalquilC3-7-alquilC0-3-C(O)-, Ph1-alquiloC0-3, Ph1-alquilC0-3-C(O)-, Ar2-alquiloC0-3, o Ar2-alquilC0-3-C(O)-; R17 es alquilo C1-4 opcionalmente sustituido con 1 a 6 sustituyentes fluoro, t-butilsulfonilo, cicloalquilC3-7-alquilC0-3-C(O)-, cicloalquilC3-7-alquilC0-3-sulfonilo, Ph1-alquiloC0-3, Ph1-alquilC0-3-C(O)-, Ph1-alquilC0-3-sulfonilo, Ar2-alquiloC0-3, Ar2-alquilC0-3-C(O)- , Ar2-alquilC0-3-sulfonilo, R19OC(O)-, o R20R21NC(O)-; R18 es hidrogeno o alquilo C1-4 opcionalmente sustituido con 1 a 6 sustituyentes fluoro, o R17 y R18, tomados junto con el átomo de nitrogeno al que están unidos forman Het1 donde Het1 está sustituido con oxo- en un átomo de carbono adyacente al átomo de nitrogeno de anillo; o R17 y R18, tomados junto con el átomo de nitrogeno al que están unidos, forman un heterociclo aromático seleccionado entre el grupo compuesto por pirolilo, pirazolilo, imidazolilo, 1,2,3-triazolilo, y 1,2,4-triazolilo; estando dicho heterociclo aromático opcionalmente sustituido con 1 a 2 sustituyentes halo, o sustituido con 1 a 2 sustituyentes alquilo C1-4 opcionalmente sustituido adicionalmente con 1 a 3 sustituyentes fluoro, o mono-sustituido con fluoro, nitro, ciano, -SCF3, o alcoxi C1-4 opcionalmente sustituido adicionalmente con 1 a 3 sustituyentes fluoro, y opcionalmente sustituido adicionalmente con un alquilo C1-4 sustituyente opcionalmente sustituido adicionalmente con 1 a 3 sustituyentes fluoro; R19 es alquilo C1-6 opcionalmente sustituido con 1 a 6 sustituyentes fluoro, cicloalquilC3-7-alquiloC0-3, Ar2-alquiloC0-3, o Ph1-alquiloC0-3; R20 es alquilo C1-6 opcionalmente sustituido con 1 a 6 sustituyentes fluoro, cicloalquilC3-7-alquiloC0-3, Ar2-alquiloC0-3, o Ph1-alquiloC0-3; R21 es hidrogeno o alquilo C1-4 opcionalmente sustituido con 1 a 6 sustituyente fluoro, R20 y R21, tomados junto con el átomo de nitrogeno al que están unidos, forman Het1; R22 es alquilo C1-6 opcionalmente sustituido con 1 a 6 sustituyentes fluoro, cicloalquilC3-7-alquiloC0-3, R23-O-, Ph1-al
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