AR066911A1 - Derivados de piperidina / piperazina - Google Patents
Derivados de piperidina / piperazinaInfo
- Publication number
- AR066911A1 AR066911A1 ARP080102427A ARP080102427A AR066911A1 AR 066911 A1 AR066911 A1 AR 066911A1 AR P080102427 A ARP080102427 A AR P080102427A AR P080102427 A ARP080102427 A AR P080102427A AR 066911 A1 AR066911 A1 AR 066911A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- nrx
- aryl
- het
- optionally substituted
- Prior art date
Links
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- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
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- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Abstract
Además, se refiere a métodos para preparar tales compuestos, composiciones farmacéuticas que comprenden dichos compuestos así como al uso como medicamentos de dichos compuestos, inhibidores de DGAT. Reivindicacion 1: Un compuesto de formula (1) que incluye cualquier forma estereoquímicamente isomérica del mismo, donde A representa CH o N; la línea punteada representa un enlace opcional en el caso en que A represente un átomo de carbono; X representa -C(=O)-; -O-C(=O)-; -C(=O)-C(=O)-; NRx-C(=O)-; -Z1-C(=O)-; -Z1-NRx-C(=O)-, -C(=O)-Z1-; -NRx-C(=O)-Z1, -S(=O)p-; -C(=S)-; -NRx-C(=S)-; -Z1-C(=S)-; -Z1-NRx-C(=S)-; -C(=S)-Z1-; -NRx-C(=S)-Z1-; Z1 representa un radical bivalente seleccionado de alcandiilo C1-6, alquendiilo C2-6 o alquindiilo C2-6; donde cada uno de dicho alcandiilo C1-6, alquendiilo C2-6 o alquindiilo C2-6 puede estar opcionalmente sustituido con hidroxilo o amino; y donde dos átomos de hidrogeno unidos al mismo carbono en el alcandiilo C1-6 pueden opcionalmente reemplazarse con alcandiilo C1-6; Y representa NRx-C(=O)-Z2-; -NRx-C(=O)-Z2-NRy-; -NRx-C(=O)-Z2-NRy-C(=O)-; -NRx-C(=O)-O-Z2-NRy-C(=O)-O-; -NRx-C(=O)-Z2-O-C(=O)-, -NRx-C(=O)-Z2-C(=O)-; -NRx-C(=O)Z2-C(=O)-O-; -NRx-C(=O)-O-Z2-C(=O)-; -NRx-C(=O)-O-Z2-C(=O)-O-, -NRx-C(=O)-O-Z2-O-C(=O)-;-NRx-C(=O)-Z2-C(=O)-NRy-; -NRc-C(=O)-Z2-NRy-C(=O)-NRy-; -C(=O)-Z2-; -C(=O)-Z2-O-; -C(=O)-NRx-Z2; -C(=O)-NRx-Z2-O-; -C(=O)-NRx-Z2-C(=O)-O-; -C(=O)-NRx-Z2-O-C(=O)-; -C(=O)-NRx-O-Z2-; -C(=O)-NRx-Z2-NRy-; -C(=O)-NRx-Z2-NRy-C(=O)-; -C(=O)-NRx-Z2-NRy-C(=O)-O-; Z2 representa un radical bivalente seleccionado de alcandiilo C1-6, alquendiilo C2-6 o alquindiilo C2-6; donde cada uno de dicho alcandiilo C1-6, alquendiilo C2-6 o alquindiilo C2-6 puede estar opcionalmente sustituido con alquiloxi C1-4, alquiltio C1-4, hidroxilo, ciano o arilo; y donde dos átomos de hidrogeno unidos al mismo átomo de carbono en la definicion de Z2 pueden opcionalmente reemplazarse con alcandiilo C1-6; Rx representa hidrogeno o alquilo C1-4; Ry representa hidrogeno; alquilo C1-4 opcionalmente sustituido con cicloalquilo C3-6 o arilo o Het; alquenilo C2-4 o -S(=O)p-ariIo; R1 representa alquilo C1-12 opcionalmente sustituido con ciano, alquiloxi C1-4, alquil-oxi C1-4-alquiloxi C1-4, cicloalquilo C3-6 o arilo; alquenilo C2-6; alquinilo C2-6; cicloalquilo C3-6; adamantanilo; arilo1, aril1alquilo C1-6; Het1 o Het1alquilo C1-6; con la salvedad de que cuando Y representa -NRx-C(=O)Z2-; -NRx-C(=O)Z2-NRy-; -NRx-C(=O)-Z2-C(=O)-NRy-; -C(=O)-Z2-; -NRx-C(=O)-Z2-NRy-C(=O)-NRy-; -C(=O)-NRx-Z2; -C(=O)-NRx-O-Z2-; o -C(=O)-NRx-Z2-NRy-; o entonces R1 puede también representar hidrogeno; R2 representa hidrogeno, alquilo C1-12, alquenilo C2-6 o R3; R3 representa cicloalquilo C3-6, fenilo, naftalenilo, 2,3-dihidro-1,4-benzodioxinilo, 1,3-benzodioxolilo, 2,3-dihidrobenzofuranilo o un heterociclo aromático de 6 miembros que contiene 1 o 2 átomos de N, donde dicho cicloalquilo C3-6, fenilo, naftalenilo, 2,3-dihidro-1,4-benzodioxinilo, 1,3-benzodioxolilo o heterociclo aromático de 6 miembros que contiene 1 o 2 átomos de N puede estar opcionalmente sustituido con al menos un sustituyente, en particular uno, dos, tres, cuatro o cinco sustituyentes, seleccionándose cada sustituyente en forma independiente de hidroxilo; carboxilo; halo; alquilo C1-6 opcionalmente sustituido con hidroxi; polihaloalquilo C1-6; alquiloxi C1-6 opcionalmente sustituido con alquiloxi C1-4; alquiltio C1-6; polihalo-alquiloxi C1-6; alquiloxicarbonilo C1-6 donde alquilo C1-6 puede estar opcionalmente sustituido con arilo; ciano; alquilcarbonilo C1-6; nitro: amino, mono o di(alquil C1-4)amino; alquilcarbonilamino C1-4; -S(=O)p-alquilo C1-4; R5R4N-C(=O)-; R5R4N-alquilo C1-6; cicloalquilo C3-6; cicloalquil C3-6-alquilo C1-4; cicloalquil C3-6-C(=O)-; arilo: ariloxi; arilalquilo C1-4; aril-C(=O)-alquilo C1-4; aril-C(=O)-; Het; Het-alquilo C1-4; Het-C(=O)-alquilo C1-4; Het-C(=O)-; Het-O-; R4 representa hidrogeno; alquilo C1-4 opcionalmente sustituido con hidroxilo o alquiloxi C1-4; R7R6N-alquilo C1-4; alquiloxi C1-4; Het; Het-alquilo C1-4; arilo; R7R6N-C(=O)-alquilo C1-4; R5 representa hidrogeno o alquilo C1-4; R6 representa hidrogeno; alquilo C1-4; alquilcarbonilo C1-4; R7 representa hidrogeno o alquilo C1-4; o R6 y R7 pueden tomarse junto con el nitrogeno al que están unidos para formar un heterociclo monocíclico saturado de 5, 6 o 7 miembros que puede además contener uno o más heteroátomos seleccionados en forma independiente de O, S, S(=O)p o N; y dicho heterociclo puede estar opcionalmente sustituido con alquilo C1-4; R8 representa hidrogeno, halo, alquilo C1-4, alquilo C1-4 sustituido con hidroxilo; arilo representa fenilo o fenilo sustituido con al menos un sustituyente, en particular uno, dos, tres, cuatro o cinco sustituyentes, seleccionándose cada sustituyente en forma independiente de hidroxilo; carboxilo; halo; alquilo C1-6 opcionalmente sustituido con alquiloxi C1-4, amino o mono o di(alquil C1-4)amino; polihaloalquilo C1-6; alquiloxi C1-6 opcionalmente sustituido con alquiloxi C1-4; alquiltio C1-6; polihaloalquiloxi C1-6; alquiloxicarbonilo C1-6; ciano; aminocarbonilo; mono o di(alquil C1-4)aminocarbonilo; alquilcarbonilo C1-6; nitro; amino; mono o di(alquil C1-4)amino; -S(=O)-alquilo C1-4; arilo1 representa fenilo, naftalenilo o fluorenilo; cada fenilo, naftalenilo o fluorenilo está opcionalmente sustituido con al menos un sustituyente, en particular uno, dos, tres, cuatro o cinco sustituyentes, seleccionándose cada uno en forma independiente de hidroxilo; oxo; carboxilo; halo; alquilo C1-6 opcionalmente sustituido con carboxilo, alcoxicarbonilo C1-4 o aril-C(=O)-; hidroxialquilo C1-6 opcionalmente sustituido con arilo o aril-C(=O)-; polihaloalquilo C1-6; alquiloxi C1-6 opcionalmente sustituido con alquiloxi C1-4; alquiltio C1-6; polihaloalquiloxi C1-6; alquiloxi C1-6-carbonilo donde alquilo C1-6 puede estar opcionalmente sustituido con arilo; ciano; aminocarbonilo; mono o di(alquil C1-4)aminocarbonilo; alquilcarbonilo C1-6; nitro; amino; mono o di(alquil C1-6)amino; R5R4N-alquilo C1-6; cicloalquil C3-6-NRx-; aril-NRx-; Het-NRx-; cicloalquil C3-6-alquil C1-4-NRx-; arilalquil C1-4-NRx; Het-alquil C1-4-NRx; -S(=O)p-alquilo C1-4; cicloalquilo C3-6; cicloalquil C3-6-alquilo C1-4; cicloalquil C3-6-C(=O)-; arilo; ariloxi; arilalquilo C1-4; aril-C(=O)-alquilo C1-4; aril-C(=O)-; Het; Het-alquilo C1-4; Het-C(=O)-alquilo C1-4; Het-C(=O)-; Het-O-; Het representa un heterociclo monocíclico no aromático o aromático que contiene al menos un heteroátomo seleccionado en forma independiente de O, S, S(=O)p o N; o un heterociclo bicíclico o tricíclico no aromático o aromático que contiene al menos un heteroátomo seleccionado en forma independiente de O, S, S(=O)p o N; dicho heterociclo monocíclico o dicho heterociclo bi o tricíclico está opcionalmente sustituido con al menos un sustituyente, en particular uno, dos, tres, cuatro o cinco sustituyentes, seleccionándose cada uno en forma independiente de hidroxilo; oxo; carboxilo; halo; alquilo C1-6 opcionalmente sustituido con alquiloxi C1-4, amino o mono o di(alquil C1-4)amino; polihaloalquilo C1-6; alquiloxi C1-6 opcionalmente sustituido con alquiloxi C1-4; alquiltio C1-6; polihaloalquiloxi C1-6; alquil C1-6-oxicarbonilo; ciano; aminocarbonilo; mono o di(alquil C1-4)aminocarbonilo; alquilcarbonilo C1-6; nitro; amino; mono o di(alquil C1-4)amino; -S(=O)p-alquilo C1-4; Het1 representa un heterociclo monocíclico no aromático o aromático que contiene al menos un heteroátomo seleccionado en forma independiente de O, S, S(=O)p- o N; o un heterociclo bicíclico o tricíclico no aromático o aromático que contiene al menos un heteroátomo seleccionado en forma independiente de O, S, S(=O)p o N; dicho heterociclo monocíclico o dicho heterociclo bi o tricíclico está opcionalmente sustituido con al menos un sustituyente, en particular uno, dos, tres, cuatro o cinco sustituyentes, seleccionándose cada uno en forma independiente de hidroxilo: oxo; carboxilo; halo; alquilo C1-6 opcionalmente sustituido con carboxilo, alcoxicarbonilo C1-4 o aril-C(=O)-; hidroxialquilo C1-6 opcionalmente sustituido con arilo o aril-C(=O)-; polihaloalquilo C1-6; alquiloxi C1-6 opcionalmente sustituido con alquiloxi C1-4; alquiltio C1-6; polihaloalquiloxi C1-6; alquiloxi C1-6-carbonilo donde alquilo C1-6 puede estar opcionalmente sustituido con arilo; ciano; aminocarbonilo; mono o di(alquil C1-4)aminocarbonilo; alquilcarbonilo C1-6; nitro; amino; mono o di(alquil C1-6)amino; R5R4N-alquilo C1-6; cicloalquil C3-6-NRx-; aril-NRx-; Het-NRx-; cicloalquil C3-6- alquil C1-4-NRx-; arilalquil C1-4-NRx-; Hetalquil C1-4-NRx-; -S(=O)p-alquilo C1-4; cicloalquilo C3-6; cicloalquil C3-6-alquilo C1-4; cicloalquil C3-6-C(=O)-; arilo; ariloxi; arilalquilo C1-4; aril-C(=O)-alquilo C1-4; aril-C(=O)-; Het; Het-alquilo C1-4; Het-C(=O)-alquilo C1-4; Het-C(=O)-; Het-O-; p representa 1 o 2: con la salvedad de que si X representa -O-C(=O)-, entonces R2 representa R3; y con la salvedad de que se excluye el compuesto de formula (2), un N-oxido de los mismos, una sal aceptable para uso farmacéutico de los mismos o un solvato de los mismos.
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-
2008
- 2008-06-06 JP JP2010510816A patent/JP5385263B2/ja active Active
- 2008-06-06 ES ES08760634.9T patent/ES2536406T3/es active Active
- 2008-06-06 PE PE2008000972A patent/PE20090362A1/es not_active Application Discontinuation
- 2008-06-06 MX MX2009013335A patent/MX2009013335A/es active IP Right Grant
- 2008-06-06 PA PA20088783601A patent/PA8783601A1/es unknown
- 2008-06-06 CN CN200880019198.0A patent/CN101678019B/zh active Active
- 2008-06-06 RU RU2009148320/04A patent/RU2470017C2/ru active
- 2008-06-06 EP EP08760634.9A patent/EP2152270B1/en active Active
- 2008-06-06 BR BRPI0813331-0A2A patent/BRPI0813331A2/pt not_active Application Discontinuation
- 2008-06-06 US US12/663,013 patent/US8981094B2/en active Active
- 2008-06-06 CA CA2687754A patent/CA2687754C/en active Active
- 2008-06-06 AR ARP080102427A patent/AR066911A1/es unknown
- 2008-06-06 WO PCT/EP2008/057060 patent/WO2008148868A1/en active Application Filing
- 2008-06-06 TW TW097121019A patent/TWI426070B/zh not_active IP Right Cessation
- 2008-06-06 CL CL2008001671A patent/CL2008001671A1/es unknown
- 2008-06-06 AU AU2008258487A patent/AU2008258487B2/en not_active Ceased
Also Published As
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BRPI0813331A2 (pt) | 2014-12-23 |
CN101678019A (zh) | 2010-03-24 |
ES2536406T3 (es) | 2015-05-25 |
PE20090362A1 (es) | 2009-04-04 |
CA2687754A1 (en) | 2008-12-11 |
EP2152270B1 (en) | 2015-03-04 |
EP2152270A1 (en) | 2010-02-17 |
CA2687754C (en) | 2015-12-08 |
CL2008001671A1 (es) | 2009-07-17 |
JP2010529089A (ja) | 2010-08-26 |
JP5385263B2 (ja) | 2014-01-08 |
US20100190789A1 (en) | 2010-07-29 |
PA8783601A1 (es) | 2009-01-23 |
TWI426070B (zh) | 2014-02-11 |
AU2008258487B2 (en) | 2012-11-15 |
MX2009013335A (es) | 2010-01-20 |
RU2009148320A (ru) | 2011-07-20 |
CN101678019B (zh) | 2016-03-30 |
WO2008148868A1 (en) | 2008-12-11 |
AU2008258487A1 (en) | 2008-12-11 |
TW200911771A (en) | 2009-03-16 |
US8981094B2 (en) | 2015-03-17 |
WO2008148868A8 (en) | 2009-03-05 |
RU2470017C2 (ru) | 2012-12-20 |
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