AR054208A1 - Derivados de oxopiperidina, su preparacion, una composicion farmaceutica y compuestos intermediarios - Google Patents

Derivados de oxopiperidina, su preparacion, una composicion farmaceutica y compuestos intermediarios

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AR054208A1
AR054208A1 AR20050103084A ARP050103084A AR054208A1 AR 054208 A1 AR054208 A1 AR 054208A1 AR 20050103084 A AR20050103084 A AR 20050103084A AR P050103084 A ARP050103084 A AR P050103084A AR 054208 A1 AR054208 A1 AR 054208A1
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cycloalkyl
heterocycloalkyl
heteroaryl
aryl
alkyl
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Alain Braun
Gilles Courtemanche
Olivier Crespin
Eykmar Fett
Cecile Pascal
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Sanofi Aventis
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Publication of AR054208A1 publication Critical patent/AR054208A1/es

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    • C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/10—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
    • C07D295/104—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
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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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    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
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    • A—HUMAN NECESSITIES
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—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
    • C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/10—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
    • C07D295/104—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/108—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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    • C07D401/02—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
    • C07D401/06—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 carbon chain containing only aliphatic carbon atoms
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    • C07D401/14—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 three or more hetero rings
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems

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  • Chemical & Material Sciences (AREA)
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  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

La presente se refiere a derivados de oxopiperidina de formula general (1), a un procedimiento para su preparacion, a medicamentos y composiciones farmacéuticas en base a ellos y a compuestos intermediarios de síntesis. Estos compuestos son de aplicacion en el tratamiento y prevencion de la obesidad, diabetes y disfunciones sexuales y el tratamiento de enfermedades cardiovasculares. Reivindicacion 1: Compuesto que responde a la formula (1): en la cual: n es igual a 1; Ra, Ra', Rb y Rb' son idénticos o diferentes entre sí, y representan un átomo de hidrogeno o un grupo alquilo o cicloalquilo, Rb y Rb' pueden formar juntos, con los átomos de carbono del ciclo al que están unidos, un puente carbonado que comprende de 4 a 5 eslabones; R1 representa un grupo alquilo o cicloalquilo; R2 representa un grupo heteroarilo; R3 representa 1 a 3 grupos, idénticos o diferentes entre sí, situados en posiciones cualesquiera del nucleo al cual están unidos, y elegidos, entre los átomos de halogeno y los grupos alquilos, cicloalquilos, -OR, -NRR', -CO-NRR', -NR-CO-R', -NR-CONRR', -NR-COOR', -NO2, -CN y -COOR; R5 representa un átomo de hidrogeno, un grupo alquilo, o cicloalquilo; R4 se elige entre los grupos de formulas (a), (b) y (c) que se presentan más adelante, eventualmente, substituidos por un grupo oxo, o mono- o polisubstituido por un grupo arilo o heteroarilo; en las cuales p = 0, 1, 2 o 3, m = 0, 1 o 2, y, o bien a) X representa un eslabon -N(R10) -, donde R10, se elige entre: ò un grupo (CH2)x-OR8, (CH2)x-COOR8, -(CH2)x-NR8R9, (CH2)x-CO-NR8R9 o -(CH2)x-NR8-COR9, -(CH2)x-COR8 en los cuales x = 1, 2, 3 o 4; ò un grupo cicloalquilo o heterocicloalquilo fusionado con un grupo arilo o heteroarilo; ò un grupo cicloalquilo, heterocicloalquilo, arilo, heteroarilo, alquilarilo, alquilheteroarilo, -CO-alquilo, -CO-cicloalquilo, -CO-heterocicloalquilo, -CO-arilo, -CO-heteroarilo, -CO-alquilarilo, -CO-alquilheteroarilo, -CS-alquilo, -CS-cicloalquilo, -CS- heterocicloalquilo, -CS-arilo, -CS-heteroarilo, -CS-alquilarilo, -CS-alquilheteroarilo, -CS-NR8R9, C(=NH)-NR8R9, -SO2-alquilo-, -SO2-cicloalquilo, -SO2-heterocicloalquilo, -SO2-arilo, -SO2-heteroarilo, -SO2-alquilarilo, -SO2-alquilheteroarilo o -SO2- NR8R9, los grupos alquilos, cicloalquilos, heterocicloalquilos, arilos, heteroarilos están eventualmente substituidos por 1 o varios grupos elegidos entre los átomos de halogeno y los grupos R, R', OR, NRR', -CO-NRR', -NRCOR', NRCONRR', -NO2, CN, - COOR, OCOR, COR,, OCONRR', NRCOOR'; los grupos cicloalquilos, heterocicloalquilos, están eventualmente fusionados con un grupo arilo o heteroarilo; o bien R10 forma con el átomo de nitrogeno al cual está unido y un átomo de carbono situado en una posicion cualquiera de la estructura cíclica de la formula (a), pero no adyacente a dicho átomo de nitrogeno, un puente que comprende de 3 a 5 eslabones, R8 y R9 se eligen, independientemente entre si, entre un átomo de hidrogeno y los grupos alquilos, cicloalquilos, heterocicloalquilos, arilos, heteroarilos, alquilarilos, alquilheteroarilos, -CO-alquilos, -CO-cicloalquilos, -CO-heterocicloalquilos, -CO-arilos, -CO-heteroarilos, -CO-alquilarilos, -CO-alquilheteroarilos, -SO2-alquilos, - SO2-cicloalquilos, -SO2-heterocicloalquilos, -SO2-arilos, -SO2-heteroarilos, -SO2-alquilarilos, -SO2-alquilheteroarilos, -C(=NH)-NRR', -COOR, -CO-NRR', -CS-NRR' y -(CH2)x-OR, donde x = 0, 1, 2, 3 o 4, los grupos alquilos, cicloalquilos, heterocicloalquilos, arilos y heteroarilos están substituidos, eventualmente, por uno o varios grupos elegidos entre los átomos de halogeno y los grupos R, R', OR, NRR', -CO-NRR', -NRCOR', NRCONRR', -NO2, CN, -COOR, OCOR, COR, OCONRR', NRCOOR'; o bien R8 y R9 forman juntos un cicloalquilo o un heterocicloalquilo; R y R' representan, independientemente entre si, un átomo de hidrogeno o un grupo alquilo, cicloalquilo, heterocicloalquilo, arilo, heteroarilo, alquilarilo o alquilheteroarilo, o pueden formar juntos un cicloalquilo o un heterocicloalquilo; o bien, b) X representa un eslabon -C(R6)(R7)-, donde R6 se elige entre: ò un átomo de hidrogeno, un átomo de halogeno; ò un grupo (CH2)x-OR8, (CH2)x-COOR8, -(CH2)x-NR8R9, (CH2)x-CO-NR8R9 o -(CH2)x-NR8-COR9, -(CH2)x-COR8 en los cuales x = 1, 2, 3 o 4; ò un grupo alquilo, cicloalquilo, heterocicloalquilo, arilo, heteroarilo, alquilarilo, alquilheteroarilo, -CO-alquilo, -CO-cicloalquilo, -CO-heterocicloalquilo, -CO-arilo, -CO- heteroarilo, -CO-alquilarilo, -CO-alquilheteroarilo, -CS-alquilo, -CS-cicloalquilo, -CS-heterocicloalquilo, -CS-arilo, -CS-heteroarilo, -CS-alquilarilo, -CS-alquilheteroarilo, -CS-NR8R9, C(=NH)-NR8R9; ò un grupo cicloalquilo o heterocicloalquilo, fusionado o no, situado en posicion espiro sobre el ciclo de formula (a) al cual está unido; un grupo cicloalquilo o heterocicloalquilo fusionado con un grupo arilo o heteroarilo; los grupos alquilos, cicloalquilos, heterocicloalquilos, arilos o heteroarilos están substituidos, eventualmente, por uno o varios grupos elegidos entre los átomos de halogeno y los grupos R, R', OR, NRR', -CO-NRR', -NRCOR', NRCONRR', -NO2, CN, -COOR, OCOR, COR, OCONRR', NRCOOR'; los grupos cicloalquilos o heterocicloalquilos están eventualmente fusionados con un grupo arilo o heteroarilo; R7 se elige entre los átomos de halogeno y los grupos alquilos, cicloalquilos, arilos, heteroarilos, alquilarilos, alquilheteroarilos, -OR, -O-arilos, -O- heteroarilos, -O-alquilarilos, -O-alquilheteroarilos, -NRR', -CO-NRR', -NR-CO-R', -NR-CO-NRR', -NR-COOR', -NO2, -CN y -COOR; R8 y R9, se eligen, independientemente entre si, entre un átomo de hidrogeno y los grupos alquilos, cicloalquilos, heterocicloalquilos, arilos, heteroarilos, alquilarilos, alquilheteroarilos, -CO-alquilos, -CO-cicloalquilos, -CO-heterocicloalquilos, -CO-arilos, -CO-heteroarilos, -CO-alquilarilos, -CO-alquilheteroarilos, -SO2-alquilos, -SO2-cicloalquilos, -SO2- heterocicloalquilos, -SO2-arilos, -SO2-heteroarilos, -SO2-alquilarilos, -SO2-alquilheteroarilos, -C(=NH)-NRR', -COOR, -CO-NRR', -CS NRR' y -(CH2)x-OR, donde x = 0, 1, 2, 3 o 4, los grupos alquilos, cicloalquilos, heterocicloalquilos, arilos y heteroarilos están substituidos, eventualmente, por uno o varios grupos elegidos entre los átomos de halogeno y los grupos R, R', OR, NRR', -CO-NRR', -NRCOR', NRCONRR', -NO2, CN, -COOR, OCOR, COR, OCONRR', NRCOOR'; o bien R8 y R9 forman juntos un cicloalquilo o un heterocicloalquilo; R y R' representan, independientemente entre si, un átomo de hidrogeno o un grupo alquilo, cicloalquilo, heterocicloalquilo, arilo, heteroarilo, alquilarilo o alquilheteroarilo, o pueden formar juntos un cicloalquilo o un heterocicloalquilo, en estado de base o de sal de adicion con un ácido, así como en estado de hidrato o de solvato.
AR20050103084A 2004-07-29 2005-07-26 Derivados de oxopiperidina, su preparacion, una composicion farmaceutica y compuestos intermediarios AR054208A1 (es)

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JP (1) JP4871866B2 (es)
KR (1) KR20070047802A (es)
CN (1) CN101010309A (es)
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AT (1) ATE459608T1 (es)
AU (1) AU2005276353C1 (es)
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FR (1) FR2873690B1 (es)
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PE (1) PE20060563A1 (es)
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FR2873691B1 (fr) * 2004-07-29 2006-10-06 Sanofi Synthelabo Derives d'amino-piperidine, leur preparation et leur application en therapeutique
RU2009108280A (ru) 2006-08-08 2010-09-20 Санофи-Авентис (Fr) Ариламиноарилалкилзамещенные имидазолидин-2,4-дионы, способы их получения, содержащие эти соединения лекарственные средства и их применение
EP2020405A1 (en) * 2007-07-30 2009-02-04 Santhera Pharmaceuticals (Schweiz) AG Substituted aryl or heteroarylpiperidine derivatives as melanocortin-4 receptor modulators
EP2025674A1 (de) 2007-08-15 2009-02-18 sanofi-aventis Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
TW201014822A (en) 2008-07-09 2010-04-16 Sanofi Aventis Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof
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WO2012120051A1 (de) 2011-03-08 2012-09-13 Sanofi Mit adamantan- oder noradamantan substituierte benzyl-oxathiazinderivate, diese verbindungen enthaltende arzneimittel und deren verwendung
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ES2341722T3 (es) 2010-06-25
UY29036A1 (es) 2006-02-24
PL1773796T3 (pl) 2010-08-31
AU2005276353B2 (en) 2011-12-01
TW200609217A (en) 2006-03-16
IL180770A0 (en) 2007-06-03
FR2873690B1 (fr) 2006-10-13
ATE459608T1 (de) 2010-03-15
DE602005019743D1 (de) 2010-04-15
DK1773796T3 (da) 2010-06-21
JP2008508240A (ja) 2008-03-21
JP4871866B2 (ja) 2012-02-08
AU2005276353A1 (en) 2006-03-02
AU2005276353C1 (en) 2012-03-29
IL180770A (en) 2011-10-31
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RU2376298C2 (ru) 2009-12-20
PT1773796E (pt) 2010-06-01
BRPI0512680A (pt) 2008-04-01
WO2006021655A2 (fr) 2006-03-02
FR2873690A1 (fr) 2006-02-03
EP1773796B1 (fr) 2010-03-03
CY1110124T1 (el) 2015-01-14
KR20070047802A (ko) 2007-05-07
RU2007107374A (ru) 2008-09-10
US20070149562A1 (en) 2007-06-28
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WO2006021655A3 (fr) 2006-04-20
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