AR038996A1 - Compuestos con efecto inhibidor sobre la gsk3, formulaciones farmaceuticas que los contienen y proceso de preparacion de los mismos - Google Patents
Compuestos con efecto inhibidor sobre la gsk3, formulaciones farmaceuticas que los contienen y proceso de preparacion de los mismosInfo
- Publication number
- AR038996A1 AR038996A1 ARP030100931A ARP030100931A AR038996A1 AR 038996 A1 AR038996 A1 AR 038996A1 AR P030100931 A ARP030100931 A AR P030100931A AR P030100931 A ARP030100931 A AR P030100931A AR 038996 A1 AR038996 A1 AR 038996A1
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- Prior art keywords
- alkyl
- formula
- oalkyl
- compound
- independently selected
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 20
- 102000001267 GSK3 Human genes 0.000 title abstract 3
- 238000002360 preparation method Methods 0.000 title abstract 3
- 108060006662 GSK3 Proteins 0.000 title abstract 2
- 230000002401 inhibitory effect Effects 0.000 title abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 2
- NFVJNJQRWPQVOA-UHFFFAOYSA-N n-[2-chloro-5-(trifluoromethyl)phenyl]-2-[3-(4-ethyl-5-ethylsulfanyl-1,2,4-triazol-3-yl)piperidin-1-yl]acetamide Chemical compound CCN1C(SCC)=NN=C1C1CN(CC(=O)NC=2C(=CC=C(C=2)C(F)(F)F)Cl)CCC1 NFVJNJQRWPQVOA-UHFFFAOYSA-N 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 22
- 125000000217 alkyl group Chemical group 0.000 abstract 18
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 8
- 229910052760 oxygen Inorganic materials 0.000 abstract 8
- 229910052717 sulfur Inorganic materials 0.000 abstract 8
- 125000005842 heteroatom Chemical group 0.000 abstract 7
- 125000000623 heterocyclic group Chemical group 0.000 abstract 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 7
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 6
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 6
- 229910052736 halogen Inorganic materials 0.000 abstract 6
- 150000002367 halogens Chemical group 0.000 abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- 239000001257 hydrogen Substances 0.000 abstract 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 6
- 125000001072 heteroaryl group Chemical group 0.000 abstract 5
- 239000002904 solvent Substances 0.000 abstract 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 4
- 125000005213 alkyl heteroaryl group Chemical group 0.000 abstract 4
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 abstract 4
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 abstract 4
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 abstract 4
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 abstract 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 4
- 125000003341 7 membered heterocyclic group Chemical group 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 2
- 101100295741 Gallus gallus COR4 gene Proteins 0.000 abstract 2
- 101100533888 Hypocrea jecorina (strain QM6a) sor4 gene Proteins 0.000 abstract 2
- 101100533877 Hypocrea jecorina (strain QM6a) sor8 gene Proteins 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 125000004429 atom Chemical group 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- 239000011737 fluorine Substances 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000004043 oxo group Chemical group O=* 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- 238000002560 therapeutic procedure Methods 0.000 abstract 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 abstract 1
- 125000001963 4 membered heterocyclic group Chemical group 0.000 abstract 1
- 208000024827 Alzheimer disease Diseases 0.000 abstract 1
- 206010012289 Dementia Diseases 0.000 abstract 1
- 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 abstract 1
- 208000018737 Parkinson disease Diseases 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 210000003169 central nervous system Anatomy 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 230000007170 pathology Effects 0.000 abstract 1
- 210000001428 peripheral nervous system Anatomy 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—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
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
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- A61P15/16—Masculine contraceptives
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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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Abstract
Compuestos de fórmula (1) y (2), así como también un procedimiento para su preparación e intermediarios usados en el mismo, formulaciones farmacéuticas que comprenden dichos compuestos terapéuticamente activos y el uso de dichos compuestos activos en terapia. Estos compuestos son apropiados para inhibir la enzima glucógeno sintasa quinasa-3 o GSK3. Ésta está altamente expresada en el sistema nervioso central y periférico y en otros tejidos por lo cual con terapia en base a estos compuestos se pueden prevenir y/o tratar trastornos asociados con demencia, enfermedad de Alzheimer, enfermedad de Parkinson y otras patologías asociadas a la marana neurofibrilar. Reivindicación 1: Un compuesto de fórmula (1) y (2), en las cuales P representa un anillo heteroaromático de 5 ó 6 miembros que contiene uno o dos heteroátomos seleccionados independientemente entre N, O y S, de los cuales, por lo menos un átomo es nitrógeno; R1 es hidrógeno; R2 y R3 están independientemente seleccionados entre halógeno, nitro, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, alquilo C0-6 - cicloalquilo C3-6, alquilarilo C0-6, alquilheteroarilo C0-6, CHO, alquilo (C0-6)OR4, Oalquilo (C1-6)OR4, alquilo (C0-6)SR4, Oalquilo (C1-6)SR4, (CO)R4, (CO)OR4, O(CO)R4, fluormetilo, difluormetilo, trifluormetilo, fluormetoxi, difluormetoxi, trifluormetoxi, Oalquilciano C1-6, alquilciano C0-6, alquilo (C1-6)CO2R4, Oalquilo (C1-6)CO2R4, O(CO)OR4, Oalquilo (C1-6)COR4 alquilo (C1-6)COR4, NR4OR5, alquilo (C0-6)NR4R5, Oalquilo (C1-6)NR4R5, alquilo (C0-6)CONR4R5, Oalquilo (C1-6)CONR4R5, Oalquilo (C1-6)NR4(CO)R5, alquilo (C0-6)NR4(CO)R5, alquilo (C0-6)NR4(CO)NR4R5, O(CO)NR4R5, NR4(CO)OR5, alquilo (C0-6)(SO2)NR4R5, Oalquilo C1-6(SO2)NR4R5, alquilo (C0-6)NR4(SO2)R5, Oalquilo (C1-6)NR4(SO2)R5, alquilo (C0-6)(SO)NR4R5, Oalquilo(C1-6)(SO)NR4R5, SO3R4, alquilo (C0-6)NR4(SO2)NR4R5, alquilo (C0-6)NR4(SO)R5, Oalquilo (C0-6)NR4(SO)R5, Oalquilo (C0-6)SO2R4, alquilo (C0-6)SO2R4, alquilo (C0-6)SOR4, Oalquilo (C1-6)SOR4 y un grupo X1R6, en el cual X1 es un enlace directo, O, CONR7R8, SO2NR9R10, SO2R11 o NR12R13; y en el cual R6 está ligado a R8, R10, R11 y R13; R7, R9 y R12 son cada uno independientemente hidrógeno o alquilo C1-6; R8, R10, R11 y R13 son alquilo C1-6; R6 es fenilo o un grupo heterocíclico de 5, 6 ó 7 miembros que contiene uno o dos heteroátomos seleccionados independientemente entre N, O y S, donde el grupo heterocíclico puede estar saturado o insaturado, o dicho fenilo o grupo heterocíclico de 5, 6 ó 7 miembros puede estar opcionalmente fusionado con un anillo saturado o insaturado de 5 ó 6 miembros que contiene átomos seleccionados independientemente entre C, N, O y S y donde el grupo fenilo o heterocíclico puede estar sustituido con uno o dos sustituyentes entre W; m es 0, 1, 2, 3 ó 4; n es 0, 1, 2, 3 ó 4; R4 está seleccionado entre hidrógeno, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, alquilo (C0-6) cicloalquilo (C3-6), alquilarilo (C0-6), alquilheteroarilo C0-6, alquilo (C1-6)NR14R15 y un grupo heterocíclico de 5 ó 6 miembros que contiene uno o dos heteroátomos seleccionados independientemente entre N, O y S, donde dicho grupo heterocíclico puede estar opcionalmente sustituido con un grupo Y; R5 está seleccionado entre hidrógeno, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, alquilo(C0-6)-cicloalquilo(C3-6), alquilarilo C0-6, alquilheteroarilo C0-6 y alquilo (C1-6)NR14R15 y; donde R4 y R5 pueden formar conjuntamente un grupo heterocíclico de 4, 5, 6 ó 7 miembros que contiene uno o más heteroátomos seleccionados independientemente entre N, O y S, donde dicho grupo heterocíclico puede estar opcionalmente sustituido con un grupo Y; y donde cualquier alquilo C1-6, alquenilo C2-6, alquinilo C2-6, alquilo(C0-6) cicloalquilo(C3-6), alquilarilo C0-6 y alquilheteroarilo C0-6 definidos bajo R2 a R5 pueden estar sustituidos con uno o más grupos Z; R14 y R15 están independientemente seleccionados entre hidrógeno, alquilo C1-6 y alquilo(C0-6)-cicloalquilo(C3-6), donde R14 y R15 pueden formar conjuntamente un grupo heterocíclico de 5 ó 6 miembros que contiene uno o más heteroátomos, seleccionados independientemente entre N, O y S, donde dicho grupo heterocíclico puede estar opcionalmente sustituido con un grupo Y; W y Z están independientemente seleccionados entre oxo, halógeno, nitro, CN, OR16, alquilo C1-6, alquilarilo C0-6, alquilo(C0-6)-cicloalquilo(C3-6), fluormetilo, difluormetilo, trifluormetilo, fluormetoxi, difluormetoxi, trifluormetoxi, Oalquilo (C1-6)NR16R17, NR16R17, CONR16R17, NR16(CO)R17, O(CO)alquilo C1-6, (CO)Oalquilo C1-6, COR16, (SO2)NR16R17, SO2R16, SOR16, (CO)alquilo (C1-6)NR16R17, (SO2)alquilo (C1-6)NR16R17, un grupo heterocíclico de 5 ó 6 miembros que contiene 1 ó 2 heteroátomos, seleccionados independientemente entre N, O y S, fenilo y heteroarilo, donde los grupos heterocíclico, fenilo o heteroarilo pueden estar opcionalmente sustituidos con un grupo Y; Y está seleccionado entre oxo, halógeno, nitro, CN, OR16, alquilo C1-6, alquilarilo C0-6, alquilo C0-6 cicloalquilo C3-6, fluormetilo, difluormetilo, trifluormetilo, fluormetoxi, difluormetoxi, trifluormetoxi, Oalquilo (C1-6)NR16R17, NR16R17, CONR16R17, NR16(CO)R17, O(CO)alquilo C1-6, (CO)Oalquilo C1-6, COR16, (SO2)NR16R17, SO2R16, SOR16, (CO)alquilo(C1-6)NR16R17, (SO2)alquilo (C1-6)NR16R17, fenilo, alquilarilo C0-6 y heteroarilo donde los grupos fenilo, alquilarilo C0-6 y heteroarilo pueden estar opcionalmente sustituidos con halógeno, nitro, CN, OR16, alquilo C1-6, fluormetilo, difluormetilo, trifluormetilo, fluormetoxi, difluormetoxi y trifluormetoxi; R16 y R17 están independientemente seleccionados entre hidrógeno y alquilo C1-6 y donde R16 y R17 pueden formar conjuntamente un grupo heterocíclico de 5 ó 6 miembros que contiene uno o más heteroátomos, seleccionados independientemente entre N, O y S; como base libre o como sal farmacéuticamente aceptable del mismo. Reivindicación 23: Un procedimiento para la preparación de un compuesto de fórmula (1) de acuerdo con la reivindicación 1, que comprende: a) hacer reaccionar un compuesto de fórmula (3), donde L1 es un grupo saliente tal como halógeno, por ejemplo flúor, cloro o bromo, con un compuesto de fórmula (4); donde R1, R2 y m son tal como se han definido en la reivindicación 1, para formar un compuesto de fórmula (1); en un solvente apropiado a una temperatura de entre +10°C y +150°C, b) hacer reaccionar un compuesto de fórmula (5) donde halo es halógeno, por ejemplo flúor, cloro o bromo, con un compuesto de fórmula (4); donde R1, R2 y m son tal como se han definido en la reivindicación 1 para formar un compuesto de fórmula (6); en un solvente apropiado a una temperatura comprendida entre +10°C y +150°C; c) hacer reaccionar un compuesto de fórmula (7), donde R4 es alquilo C1-6, con la amina apropiada HNR4R5, para formar un compuesto de fórmula (8); que se lleva a cabo mediante; i) reacción del compuesto de fórmula (7) con la amina apropiada R4R5NH en un solvente adecuado en presencia de un reactivo apropiado a una temperatura de reacción entre 0°C y reflujo; o ii) la reacción del compuesto de la fórmula (7) con la amina apropiada R4R5NH sola o en un solvente adecuado con o sin base apropiada a una temperatura entre -20°C y +150°C; d) la reducción del n-óxido en el compuesto de fórmula (9), para formar un compuesto de fórmula (10) mediante el uso de un reactivo adecuado en un solvente adecuado a una temperatura entre 0°C y + 100°C.
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2007
- 2007-06-13 JP JP2007155810A patent/JP2007224051A/ja active Pending
-
2008
- 2008-06-17 US US12/140,510 patent/US20090149460A1/en not_active Abandoned
-
2009
- 2009-02-19 CY CY20091100196T patent/CY1108823T1/el unknown
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