AR084290A1 - Inhibidores de neprilisina, metodos para su preparacion e intermediarios utilizados en los mismos, composiciones farmaceuticas que los comprenden y su uso en la fabricacion de medicamentos para tratar enfermedades mediadas por la inhibicion de nep - Google Patents
Inhibidores de neprilisina, metodos para su preparacion e intermediarios utilizados en los mismos, composiciones farmaceuticas que los comprenden y su uso en la fabricacion de medicamentos para tratar enfermedades mediadas por la inhibicion de nepInfo
- Publication number
- AR084290A1 AR084290A1 ARP110104683A AR084290A1 AR 084290 A1 AR084290 A1 AR 084290A1 AR P110104683 A ARP110104683 A AR P110104683A AR 084290 A1 AR084290 A1 AR 084290A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- phenyl
- benzyl
- cycloalkyl
- halo
- Prior art date
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
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Abstract
Estos compuestos tienen actividad de inhibición de neprilisina. Composiciones farmacéuticas que comprenden dichos compuestos; métodos para usar dichos compuestos; y proceso e intermediarios para preparar dichos compuestos.Reivindicación 1: Un compuesto caracterizado porque es de fórmula (1), donde: R1 se selecciona entre -OR7 y -NR8R9; R2 es H o -P(O)(OH)2 o R2 se toma junto con R7 para formar -CR18R19- o se toma junto con R8 para formar -C(O)-; X es un -heteroarilo C1-9; R3 se encuentra ausente o se selecciona entre H; halo; -alquilen C0-5-OH; -NH2; -alquilo C1-6; -CF3; -cicloalquilo C3-7; -alquilen C0-2-O-alquilo C1-6; -C(O)R20; -alquilen C0-1-COOR21; -C(O)NR22R23; -NHC(O)R24; =O; -NO2; -C(CH3)=N(OH); fenilo opcionalmente sustituido con uno o dos grupos seleccionados en forma independiente entre halo, -OH, -CF3, -OCH3, -NHC(O)CH3, y fenilo; naftalenilo; piridinilo; pirazinilo; pirazol opcionalmente sustituido con metilo; tiofenilo opcionalmente sustituido con metilo o halo; furanilo; y -CH2-morfolinilo; y R3, cuando está presente, se une a un átomo de carbono; R4 se encuentra ausente o se selecciona entre H; -OH; -alquilo C1-6; -alquilen C1-2-COOR35; -CH2OC(O)CH(R36)NH2; -OCH2OC(O)CH(R36)NH2; -OCH2OC(O)CH3; -CH2OP(O)(OH)2; -CH2CHOHCH2OH; -CH[CH(CH3)2]-NHC(O)O-alquilo C1-6; piridinilo; y fenilo o bencilo opcionalmente sustituido con uno o más grupos seleccionados entre halo, -COOR35, -OCH3, -OCF3, y -SCF3; y R4, cuando está presente, se une a un átomo de carbono o nitrógeno; o R3 y R4 se toman juntos para formar -fenilen-O-(CH2)1-3- o -fenilen-O-CH2-CHOH-CH2-; a es 0 ó 1; R5 se selecciona entre halo, -CH3, -CF3, y -CN; b es 0 o un entero entre 1 y 3; cada R6 se selecciona en forma independiente entre halo, -OH, -CH3, -OCH3, y -CF3; R7 se selecciona entre H, -alquilo C1-8, -alquilen C1-3-arilo C6-10, -alquilen C1-3-heteroarilo C1-9, -cicloalquilo C3-7, -[(CH2)2O]1-3CH3, -alquilen C1-6-OC(O)R10, -alquilen C1-6-NR12R13, -alquilen C1-6-C(O)R31, -alquilen C0-6morfolinilo; -alquilen C1-6-SO2-alquilo C1-6; o un resto del grupo de fórmulas (2); R10 se selecciona entre -alquilo C1-6, -O-alquilo C1-6, -cicloalquilo C3-7, -O-cicloalquilo C3-7, fenilo, -O-fenilo, -NR12R13, -CH[CH(CH3)2]-NH2, -CH[CH(CH3)2]-NHC(O)O-alquilo C1-6, y -CH(NH2)CH2COOCH3; y R12 y R13 se seleccionan en forma independiente entre H, -alquilo C1-6, y bencilo; o R12 y R13 se toman juntos como -(CH2)3-6-, -C(O)-(CH2)3-, o -(CH2)2O(CH2)2-; y R31 se selecciona entre -O-alquilo C1-6, -O-bencilo, y -NR12R13; R32 es -alquilo C1-6 o -alquilen C0-6-arilo C6-10; R8 se selecciona entre H, -OH, -OC(O)R14, -CH2COOH, -O-bencilo, piridilo, y -OC(S)NR15R16; R14 se selecciona entre H, -alquilo C1-6, -arilo C6-10, -OCH2-arilo C6-10, -CH2O-arilo C6-10, y -NR15R16; y R15 y R16 se seleccionan en forma independiente entre H y -alquilo C1-4; R9 se selecciona entre H, -alquilo C1-6, y -C(O)R17; y R17 se selecciona entre H, -alquilo C1-6, -cicloalquilo C3-7, -arilo C6-10, y -heteroarilo C1-9; R18 y R19 se seleccionan en forma independiente entre H, -alquilo C1-6, y -O-cicloalquilo C3-7, o R18 y R19 se toman juntos para formar =O; R20 se selecciona entre H y -alquilo C1-6; R21 y R35 se seleccionan en forma independiente entre H, -alquilo C1-6, -alquilen C1-3-arilo C6-10, -alquilen C1-3-heteroarilo C1-9, -cicloalquilo C3-7, -[(CH2)2O]1-3CH3, -alquilen C1-6-OC(O)R25; -alquilen C1-6-NR27R28, -alquilen C1-6-C(O)R33, -alquilen C0-6morfolinilo, -alquilen C1-6-SO2-alquilo C1-6, o un resto del grupo de fórmulas (3); R25 se selecciona entre -alquilo C1-6, -O-alquilo C1-6, -cicloalquilo C3-7, -O-cicloalquilo C3-7, fenilo, -O-fenilo, -NR27R28, -CH[CH(CH3)2]-NH2, -CH[CH(CH3)2]-NHC(O)O-alquilo C1-6, y -CH(NH2)CH2COOCH3; R27 y R28 se seleccionan en forma independiente entre H, -alquilo C1-6, y bencilo; o R27 y R28 se toman juntos como -(CH2)3-6-, -C(O)-(CH2)3-, o -(CH2)2O(CH2)2-; R33 se selecciona entre -O-alquilo C1-6, -O-bencilo, y -NR27R28; y R34 es -alquilo C1-6 o -alquilen C0-6-arilo C6-10; R22 y R23 se seleccionan en forma independiente entre H, -alquilo C1-6, -CH2COOH, -(CH2)2OH; -(CH2)2OCH3, -(CH2)2SO2NH2, -(CH2)2N(CH3)2, -alquilen C0-1-cicloalquilo C3-7, y -(CH2)2-imidazolilo; o R22 y R23 se toman juntos para formar un -heterociclo C3-5 saturado o parcialmente insaturado opcionalmente sustituido con halo, -OH, -COOH, o -CONH2; y que contiene opcionalmente un átomo de oxígeno en el anillo; R24 se selecciona entre -alquilo C1-6; -alquilen C0-1-O-alquilo C1-6; fenilo opcionalmente sustituido con halo o -OCH3 y -heteroarilo C1-9; y R36 se selecciona entre H, -CH(CH3)2, fenilo, y bencilo; donde cada grupo alquilo en R1, R3, y R4 está opcionalmente sustituido con entre 1 y 8 átomos de flúor; y; donde el ligando metileno en el bifenilo está opcionalmente sustituido con uno o dos grupos -alquilo C1-6 o ciclopropilo; o una sal farmacéuticamente aceptable de los mismos. Reivindicación 19: Un intermediario útil en la síntesis de un compuesto de acuerdo con cualquiera de las reivindicaciones 1 a 17, caracterizado porque es de fórmula (4) donde P1 es H o un grupo protector de amino seleccionado entre t-butoxicarbonilo, tritilo, benciloxicarbonilo, 9-fluorenilmetoxicarbonilo, formilo, trimetilsililo, y t-butildimetilsililo; o una sal del mismo. Reivindicación 21: Un intermediario útil en la síntesis de un compuesto de acuerdo con cualquiera de las reivindicaciones 1 a 17, caracterizado porque se selecciona entre los compuestos de fórmula (5), (6), (7) u (8), o una sal del mismo; donde R1P se selecciona entre -O-P3, -NHP2, y -NH(O-P4); R3P se selecciona entre -alquilen C0-5-O-P4, -alquilen C0-1-COO-P3, y fenilo sustituido con -O-P4; R4P se selecciona entre -O-P4; -alquilen C1-2-COO-P3; y fenilo o bencilo sustituido con -COO-P3; P2 es un grupo protector de amino seleccionado entre t-butoxicarbonilo, tritilo, benciloxicarbonilo, 9-fluorenilmetoxicarbonilo, formilo, trimetilsililo, y t-butildimetilsililo; P3 es un grupo protector de carboxi seleccionado entre metilo, etilo, t-butilo, bencilo, p-metoxibencilo, 9-fluorenilmetilo, trimetilsililo, t-butildimetilsililo, y difenilmetilo; y P4 es un grupo protector de hidroxilo seleccionado entre -alquilo C1-6, trialquilsililo C1-6, -alcanoilo C1-6, benzoilo, bencilo, p-metoxibencilo, 9-fluorenilmetilo, y difenilmetilo.
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ARP110104683 AR084290A1 (es) | 2010-12-15 | 2011-12-14 | Inhibidores de neprilisina, metodos para su preparacion e intermediarios utilizados en los mismos, composiciones farmaceuticas que los comprenden y su uso en la fabricacion de medicamentos para tratar enfermedades mediadas por la inhibicion de nep |
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EP (1) | EP2651900B1 (es) |
JP (2) | JP5944922B2 (es) |
KR (1) | KR101892611B1 (es) |
CN (1) | CN103261168B (es) |
AR (1) | AR084290A1 (es) |
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BR (1) | BR112013014952A2 (es) |
CA (1) | CA2819153A1 (es) |
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IL (1) | IL226451A (es) |
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TW (1) | TWI523843B (es) |
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- 2011-12-14 MX MX2013006802A patent/MX354476B/es active IP Right Grant
- 2011-12-14 EP EP11805709.0A patent/EP2651900B1/en active Active
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- 2011-12-14 WO PCT/US2011/064837 patent/WO2012082857A1/en active Application Filing
- 2011-12-14 KR KR1020137018340A patent/KR101892611B1/ko active IP Right Grant
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- 2011-12-14 US US13/325,453 patent/US8563512B2/en active Active
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- 2011-12-14 ES ES11805709.0T patent/ES2548887T3/es active Active
- 2011-12-14 CN CN201180060322.XA patent/CN103261168B/zh active Active
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- 2013-09-12 US US14/024,974 patent/US9120758B2/en active Active
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