AR040079A1 - 3-aminopirazoles n-sustituidos como inhibidores para el tratamiento de los desordenes proliferativos de las celulas, composicion farmaceutica y metodos de preparacion - Google Patents
3-aminopirazoles n-sustituidos como inhibidores para el tratamiento de los desordenes proliferativos de las celulas, composicion farmaceutica y metodos de preparacionInfo
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- AR040079A1 AR040079A1 ARP030101696A ARP030101696A AR040079A1 AR 040079 A1 AR040079 A1 AR 040079A1 AR P030101696 A ARP030101696 A AR P030101696A AR P030101696 A ARP030101696 A AR P030101696A AR 040079 A1 AR040079 A1 AR 040079A1
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- Prior art keywords
- alkyl
- nhc
- group
- benzo
- fused
- Prior art date
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- 238000002360 preparation method Methods 0.000 title abstract 4
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 3
- 239000003112 inhibitor Substances 0.000 title abstract 2
- 230000002062 proliferating effect Effects 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 113
- 125000000592 heterocycloalkyl group Chemical group 0.000 abstract 16
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 15
- 125000003545 alkoxy group Chemical group 0.000 abstract 13
- 125000004001 thioalkyl group Chemical group 0.000 abstract 12
- -1 cyano, hydroxy Chemical group 0.000 abstract 11
- 125000001072 heteroaryl group Chemical group 0.000 abstract 10
- 125000003342 alkenyl group Chemical group 0.000 abstract 8
- 125000003118 aryl group Chemical group 0.000 abstract 7
- 125000003282 alkyl amino group Chemical group 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 6
- 229910052736 halogen Inorganic materials 0.000 abstract 5
- 150000002367 halogens Chemical class 0.000 abstract 5
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 4
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 4
- 238000000034 method Methods 0.000 abstract 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- 108091008606 PDGF receptors Proteins 0.000 abstract 2
- 125000005605 benzo group Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 230000003287 optical effect Effects 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 abstract 2
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical class NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- 102000011653 Platelet-Derived Growth Factor Receptors Human genes 0.000 abstract 1
- 125000004367 cycloalkylaryl group Chemical group 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 238000001647 drug administration Methods 0.000 abstract 1
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- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/65031—Five-membered rings having the nitrogen atoms in the positions 1 and 2
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Abstract
La presente está dirigida a derivados 3-aminopirazol tricíclicos N-sustituidos, que son utilizados como inhibidores de la quinasa de receptor del factor de crecimiento derivado de plaquetas (PDGF-R), y los métodos para la preparación de dichos derivados. La presente está dirigida además a las composiciones farmacéuticas que comprenden los compuestos de la presente, a los métodos para tratar las afecciones tales como tumores y otros desórdenes proliferativos de células, a los procesos de preparación del compuesto y de las composiciones farmacéuticas y a un dispositivo para administración de la droga Reivindicación 1: Un compuesto de fórmula (1): en la cual, n es un número entero de 1 a 4; R1 está seleccionado del grupo que consiste en hidrógeno, alquilo inferior, -OH-alcoxi, -oxo, -NH2, -NH(alquilo) y -N(alquilo)2; el anillo A está seleccionado del grupo que consiste en un arilo, un heteroarilo monocíclico de cinco a seis miembros, un heteroarilo benzo-fusionado de nueve a diez miembros, un grupo heterocicloalquilo benzo-fusionado de nueve a diez miembros, y un grupo cicloalquilo benzo-fusionado de nueve a diez miembros; donde el heteroarilo benzo-fusionado, el heterocicloalquilo benzo-fusionado o el grupo cicloalquilo benzo-fusionado está adherido a la molécula de manera que el anillo fenilo está directamente ligado a la porción de fórmula (2) de la molécula; p es un número entero de 0 a 2; R2 está seleccionado del grupo que consiste en: un resto de fórmula (3), y -X-A1-Y-A2; en la cual, X e Y están cada uno independientemente ausentes o están seleccionados del grupo que consiste en -O-, -NH-, -N(alquilo)-, S-, -SO-, -SO2-, -OC(=O), -C(=O)O-, -NHC(=O)-, -N(alquilo)C(=O)-, -C(=O)NH-, -C(=O)N(alquilo)-, -OC(=O)O-, -NHC(=O)O-, -OC(=O)NH-, -N(alquilo)C(=O)O-, -OC(=O)N(alquilo)-, -NHC(=O)NH-, -NHC(=O)N(alquilo)-, -N(alquilo)C(=O)NH-, -N(alquilo)C(=O)N(alquilo)-, -NHSO2-, -SO2NH-, -N(alquilo)SO2- y -SO2N(alquilo)-; A1 está ausente o está seleccionado entre alquilo o alquenilo; A2 está seleccionado entre alquilo, alquenilo, o H; donde, cuando A1 o A2 es alquilo o alquenilo, el grupo alquilo o alquenilo puede estar opcionalmente sustituido con uno o más grupos independientemente seleccionados de halógeno, ciano, hidroxi, alcoxi, tio, alcoxi halogenado, -OC(=O)alquilo, -OC(=O)Oalquilo, amino, alquilamino, -NHC(=O)alquilo, -N(alquilo)C(=O)alquilo, dialquilamino, -NHC(=O)NH2, -NHC(=O)NHalquilo, -N(alquilo)C(=O)NHalquilo, -(alquilo)C(=O)NH2, -OC(=O)NHalquilo, -NHC(=O)Oalquilo, -N(alquilo)C(=O)Oalquilo, -NHSO2alquilo, -N(alquilo)SO2alquilo, tioalquilo, tioalquilo halogenado, -SO2alquilo, -SO2alquilo halogenado, -NHC(=O)N(alquilo)2, -N(alquilo)C(=O)N(alquilo)2 o -OC(=O)N(alquilo)2; el anillo D está seleccionado del grupo que consiste en un arilo a cicloalquilo, un carbociclo parcialmente insaturado, un heteroarilo, un heterocicloalquilo, un cicloalquilo benzo-fusionado de nueve a diez miembros, y un heterocicloalquilo benzo-fusionado de nueve a diez miembros; donde el arilo, cicloalquilo, carbociclo parcialmente insaturado, heteroarilo, heterocicloalquilo, cicloalquilo, benzo-fusionado o heterocicloalquilo benzo-fusionado, está opcionalmente sustituido con uno o más sustituyentes independientemente seleccionados de halógeno, hidroxi, amino, tio, nitro, ciano, alquilo, alquilo halogenado, alcoxi, alcoxi halogenado, alquilamino, -NHC(=O)alquilo, -N(alquilo)C(=O)alquilo, o dialquilimino, -NHC(=O)NH2, -NHC(=O)NHalquilo, -N(alquilo)C(=O)NHalquilo, -OC(=O)NHalquilo, -NHC(=O)Oalquilo, -N(alquilo)C(=O)Oalquilo, -NHSO2alquilo, -N(alquilo)SO2alquilo, tioalquilo, tioalquilo halogenado, -SO2alquilo, halogenado, -SO2alquilo, -NHC(=O)N(alquilo)2, -N(alquilo)C(=O)N(alquilo)2 o OC(=O)N(alquilo)2; q es un número entero de 0 a 4; R3 está seleccionado del grupo que consiste en halogenado, hidroxi, amino, tio, nitro, ciano, alquilo, alquilo halogenado, alcoxi, alquiloxi halogenado, alquilamino, -NHC(=O)alquilo, -N(alquilo)C(=O)alquilo, o dialquilamino, -NHC(=O)NH2, -NHC(=O)NHalquilo, -N(alquilo)C(=O)NHalquilo, -OC(=O)NHalquilo, -NHC(=O)Oalquilo, -N(alquilo)C(=O)Oalquilo, -NHSO2alquilo, -N(alquilo)SO2alquilo, tioalquilo, tioalquilo halogenado, -SO2alquilo, -SO2alquilo halogenado, -NHC(=O)N(alquilo)2, -N(alquilo)C(=O)N(alquilo)2 y -OC(=O)N(alquilo)2; con la condición de que la suma p y q es un número entero de 0 a 4; L1 esta ausente o está seleccionado del grupo que consiste en alquilo; el anillo B está seleccionado del grupo que consiste en un arilo, un cicloalquilo, un carbociclo parcialmente insaturado, un heteroarilo, un heterocicloalquilo, un cicloalquilo benzo-fusionado de nueve a diez miembros, y un heterocicloalquilo benzo-fusionado de nueve a diez miembros; o un isómero óptico, un enantiómero, un diasterómero, un racemato o una sal farmacéuticamente aceptable del mismo. Reivindicación 71: Un procedimiento para la preparación de un compuesto de la fórmula (1): en la cual, n es un número entero de 1 a 4; R1 está seleccionado del grupo que consiste en hidrógeno, alquilo inferior, -OH, alcoxi, -oxo, -NH2, -NH(alquilo) y -N(alquilo)2; el anillo A está seleccionado del grupo que consiste en un arilo, un heteroarilo monocíclico de cinco a seis miembros, un heteroarilo benzo-fusionado de nueve a diez miembros, un grupo heterocicloalquilo benzo-fusionado de nueve a diez miembros, y un grupo cicloalquilo benzo-fusionado de nueve a diez miembros; donde el heteroarilo benzo-fusionado, el heterocicloalquilo benzo-fusionado o el grupo cicloalquilo benzo-fusionado está adherido a la molécula de manera que el anillo fenilo está directamente ligado a la porción de fórmula (2) de la molécula; p es un número entero de 0 a 2; R2 está seleccionado del grupo que consiste en: un resto de fórmula (3), y -X-A1-Y-A2; donde, X e Y están cada uno independientemente ausentes o están seleccionados del grupo que consiste en -O-, -NH-, -N(alquilo)-, S-, -SO-, -SO2-, -OC(=O), -C(=O)O-, -NHC(=O)-, -N(alquilo)C(=O)-, -C(=O)NH-, -C(=O)N(alquilo)-, -OC(=O)O-, -NHC(=O)O-, -OC(=O)NH-, -N(alquilo)C(=O)O-, -OC(=O)N(alquilo)-, -NHC(=O)NH-, -NHC(=O)N(alquilo)-, -N(alquilo)C(=O)NH-, -N(alquilo)C(=O)N(alquilo)-, -NHSO2-, -SO2NH-, -N(alquilo)SO2- y -SO2N(alquilo)-; A1 está ausente o está seleccionado entre alquilo o alquenilo; A2 está seleccionado entre alquilo, alquenilo, o H; donde, cuando A1 o A2 es alquilo o alquenilo, el grupo alquilo o alquenilo puede estar opcionalmente sustituido con uno o más grupos independientemente seleccionados de halógeno, ciano, hidroxi, alcoxi, tio, alcoxi halogenado, -OC(=O)alquilo, -OC(=O)Oalquilo, amino, alquilamino, -NHC(=O)alquilo, -N(alquilo)C(=O)alquilo, diaquilamino, -NHC(=O)NH2, -NHC(=O)NHalquilo, -N(alquilo)C(=O)NHalquilo, -N(alquilo)C(=O)NH2, -OC(=O)NHalquilo, -NHC(=O)Oalquilo, -N(alquilo)C(=O)Oalquilo, -NHSO2alquilo, -N(alquilo)SO2alquilo, tioalquilo, tioalquilo halogenado, -SO2alquilo, -SO2alquilo, -SO2alquilo halogenado, -NHC(=O)N(alquilo)2, -N(alquilo)C(=O)N(alquilo)2 o -OC(=O)N(alquilo)2; el anillo D está seleccionado del grupo que consiste en un arilo, un cicloalquilo, un carbociclo parcialmente insaturado, un heteroarilo, un heterocicloalquilo, un cicloalquilo benzo-fusionado de nueve a diez miembros, y un heterocicloalquilo benzo-fusionado de nueve a diez miembros; donde el arilo, cicloalquilo, carbociclo parcialmente insaturado, heteroarilo, heterocicloalquilo, cicloalquilo benzo-fusionado o heterocicloalquilo benzo-fusionado, está opcionalmente sustituido con uno o más sustituyentes independientemente seleccionados de halógeno, hidroxi, amino, tio, nitro, ciano, alquilo, alquilo halogenado, alcoxi, alcoxi halogenado, alquilamino, -NHC(=O)alquilo, -N(alquilo)C(=O)alquilo, o dialquilamino, -NHC(=O)NH2, -NHC(=O)NHalquilo, -N(alquilo)C(=O)NHalquilo, -OC(=O)NHalquilo, -NHC(=O)Oalquilo, -N(alquilo)C(=O)Oalquilo, -NHSO2alquilo, -N(alquilo)SO2alquilo, tioalquilo, tioalquilo halogenado, -SO2alquilo, -SO2alquilo halogenado, -NHC(=O)N(alquilo)2, -N(alquilo)C(=O)N(alquilo)2 o OC(=O)N(alquilo)2; q es un número entero de 0 a 4; R3 está seleccionado del grupo que consiste en halógeno, hidroxi, amino, tio, nitro, ciano, alquilo, alquilo halogenado, alcoxi, alquiloxi halogenado, alquilamino, -NHC(=O)alquilo, -N(alquilo)C(=O)alquilo, o dialquilamino, -NHC(=O)NH2, -NHC(=O)NHalquilo, -N(alquilo)C(=O)NHalquilo, -OC(=O)NHalquilo, -NHC(=O)Oalquilo, -N(alquilo)C(=O)Oalquilo, -NHSO2alquilo, -N(alquilo)SO2alquilo, tioalquilo, tioalquilo halogenado, -SO2alquilo, -SO2alquilo halogenado, -NHC(=O)N(alquilo)2, -N(alquilo)C(=O)N(alquilo)2 y -OC(=O)N(alquilo)2; con la condición de que la suma p y q es un número entero de 0 a 4; L1 esta ausente o está seleccionado del grupo que consiste en alquilo; el anillo B está seleccionado del grupo que consiste en un arilo, un cicloalquilo, un carbociclo parcialmente insaturado, un heteroarilo, un heterocicloalquilo, un cicloalquilo benzo-fusionado de nueve a diez miembros, y un heterocicloalquilo benzo-fusionado de nueve a diez miembros; o un isómero óptico, un enantiómero, un diastereómero, un racemato o una sal farmacéuticamente aceptable del mismo; que comprende un resto de fórmula (4), hacer reaccionar un compuesto de fórmula (4) con hidrazina, para proporcionar el correspondiente compuesto de la fórmula (1).
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2003
- 2003-05-13 PL PL03374062A patent/PL374062A1/xx not_active Application Discontinuation
- 2003-05-13 KR KR10-2004-7018454A patent/KR20040106554A/ko not_active Application Discontinuation
- 2003-05-13 JP JP2004505342A patent/JP2006502097A/ja not_active Withdrawn
- 2003-05-13 MX MXPA04011320A patent/MXPA04011320A/es active IP Right Grant
- 2003-05-13 RS YU98804A patent/RS98804A/sr unknown
- 2003-05-13 MY MYPI20031800A patent/MY138268A/en unknown
- 2003-05-13 DE DE60326950T patent/DE60326950D1/de not_active Expired - Fee Related
- 2003-05-13 AT AT03728909T patent/ATE427301T1/de not_active IP Right Cessation
- 2003-05-13 AU AU2003234567A patent/AU2003234567A1/en not_active Abandoned
- 2003-05-13 CN CNB038164884A patent/CN100396670C/zh not_active Expired - Fee Related
- 2003-05-13 BR BRPI0311179A patent/BRPI0311179A2/pt not_active IP Right Cessation
- 2003-05-13 NZ NZ548796A patent/NZ548796A/en unknown
- 2003-05-13 ES ES03728909T patent/ES2323952T3/es not_active Expired - Lifetime
- 2003-05-13 EP EP03728909A patent/EP1506175B1/en not_active Expired - Lifetime
- 2003-05-13 UA UA20041109391A patent/UA80820C2/uk unknown
- 2003-05-13 CA CA002486097A patent/CA2486097A1/en not_active Abandoned
- 2003-05-13 WO PCT/US2003/015193 patent/WO2003097609A1/en active Application Filing
- 2003-05-13 EA EA200401378A patent/EA008770B1/ru not_active IP Right Cessation
- 2003-05-14 US US10/438,152 patent/US7196110B2/en not_active Expired - Lifetime
- 2003-05-14 TW TW092113012A patent/TW200407311A/zh unknown
- 2003-05-15 AR ARP030101696A patent/AR040079A1/es not_active Application Discontinuation
- 2003-05-15 UY UY27811A patent/UY27811A1/es not_active Application Discontinuation
- 2003-05-15 PE PE2003000466A patent/PE20040758A1/es not_active Application Discontinuation
- 2003-12-07 SA SA03240431A patent/SA03240431A/ar unknown
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2004
- 2004-11-14 IL IL16519704A patent/IL165197A0/xx unknown
- 2004-11-15 CR CR7574A patent/CR7574A/es not_active Application Discontinuation
- 2004-12-14 HR HR20041188A patent/HRP20041188A2/xx not_active Application Discontinuation
- 2004-12-14 NO NO20045451A patent/NO20045451L/no unknown
- 2004-12-14 ZA ZA200410108A patent/ZA200410108B/en unknown
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2007
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