BRPI0606905B1 - Derivados de quinazolina tendo atividade inibitória de tirosina cinase e composição farmacêutica que os compreende - Google Patents

Derivados de quinazolina tendo atividade inibitória de tirosina cinase e composição farmacêutica que os compreende Download PDF

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BRPI0606905B1
BRPI0606905B1 BRPI0606905-3A BRPI0606905A BRPI0606905B1 BR PI0606905 B1 BRPI0606905 B1 BR PI0606905B1 BR PI0606905 A BRPI0606905 A BR PI0606905A BR PI0606905 B1 BRPI0606905 B1 BR PI0606905B1
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Masaharu Kume
Kenji Matsuo
Naoki Omori
Masami Takayama
Aiko OMORI
Takeshi Endo
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Shionogi & Co., Ltd.
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    • A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
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Abstract

derivados de quinazolina tendo atividade inibitória de tirosina cinase e composição farmacêutica contendo-os. a presente invenção refere-se a um composto que inibe tanto a tirosina cinase do receptor egf quanto a tirosina cinase her2. composto representado pela fórmula geral (i): fórmula química 1 (i) em que rx é um grupo representado pela fórmula: fórmula químca 2 em que r1 é um átomo de hidrogênio, alquila opcionalmente substituida, etc.; z é -o-, -n(r10)-, etc.; r10 é um átomo de hidrogênio, alquila, etc.; r2 é um átomo de hidrogênio, alquila opcionalmente substituida, etc.; r18 é um átomo de hidrogênio, alquila opcionalmente substituida, etc.; r19 é alquila opcionalmente substituida, etc.; w1 e um grupo contendo nitrogênio não aromático opcionalmente substituído; r17 é um átomo de hidrogênio, alquila opcionalmente substituida, etc.; r3 e r4 são independentemente um átomo de hidrogênio, alquila opcionalmente substituída, etc.; x é -o-, -s-, ou -n(r12)-, etc.; r12 é um átomo de hidrogênio, alquila, etc.; e a é fenila opcionalmente tendo um substituinte, etc., seu sal farmaceuticamente aceitável, ou um solvato do mesmo.

Description

Campo Técnico
[001] A presente invenção refere-se a um composto que inibe tanto a tirosina cinase receptora de EGF quanto a tirosina cinase HER2, e a uma composição farmacêutica contendo o mesmo como ingrediente ativo.
Antecedentes da Técnica
[002] Tirosina cinase é uma enzima que fosforila resíduos tirosina em proteínas de substratos, e sabe-se que desempenha um papel importante no sistema de transdução de sinal intracelular no que se refere à diferenciação e proliferação celular. Duas tirosina cinases receptoras, o receptor de EGF (doravante EGFR) e HER2 (também chamada ErbB2 ou Neu) estão consideravelmente envolvidos no desenvolvimento de câncer, e suas atividades são aumentadas em vários cânceres humanos (Literatura Não-Patentiada 1, Literatura Não- Patentiada 2 e Literatura Não-Patentiada 3). Também se sabe que essas cinases são expressas de forma aberrante em cânceres de cérebro, pulmão, estômago, intestino, pâncreas, cabeça e pescoço, esôfago, bexiga, rim, próstata, ovário, mama, útero, e glândula tireóide (Literatura Não-patentiada 4 e Literatura Patentiada 1). Portanto, acredita-se que um inibidor dessas cinases seja útila como fármaco anticâncer que pode ser eficaz em muitos tipos de cânceres e tem pouco efeito colateral. Como inibidor de tirosina cinases, são conhecidos os compostos descritos na Literatura Patentiada 2, Literatura Patentiada 3, Literatura Patentiada 4, Literatura Patentiada 5, Literatura Patentiada 6, Literatura Patentiada 7.
[003] Além disso, sabe-se que a transformação celular devido ao EGFR é acelerada pela coexpressão adicional de HER2 (Literatura Não- patentiada 5). Ademais, a expressão concomitante de EGFR e HER2 é relatada como um marcador de pobre prognóstico na mama, cavidade oral e cânceres de pulmão (Literatura Não-patentiada 6). Como uma fármaco que inibe tanto o EGFR quanto o HER2, são conhecidos os compostos descritos na Literatura Patentiada 8.
[004] Um agente anticâncer tendo um substituinte tipo oxima na posição 4 de um derivado de quinazolina está descrito na Literatura Patentiada 9 e Literatura Patentiada 10. Literatura Patentiada 1 - Pedido de Patente Japonesa Aberto à Inspeção Pública (JP-A) N° 5-208911 Literatura Patentiada 2 - WO 92/20642 Literatura Patentiada 3 - EPA N° 92305703.8 Literatura Patentiada 4 - EPA N° 0566266 Literatura Patentiada 5 - EPA N° 0602851 Literatura Patentiada 6 - EPA N° 0520722 Literatura Patentiada 7 - WO 98/02434 Literatura Patentiada 8 - WO 02/066445 Literatura Patentiada 9 - WO 2004/0691545 Literatura Patentiada 10 - WO 2004/105765 Literatura Não-patentiada 1 - Cancer Res., 1991, vol.51, pp. 4430-4435 Literatura Não-patentiada 2 - Cancer Res., 1992, vol.52, pp. 3636-3641 Literatura Não-patentiada 3 - Cancer Chemother. Pharmacol., 1993, vol.32, pp. 1-19 Literatura Não-patentiada 4 - Expart. Opin. Invest. Drugs, 1994, vol.3, No.6, pp. 577-595 Literatura Não-patentiada 5 - Cell, 1987, vol.58, pp. 287-292 Literatura Não-patentiada 6 - Clin. Cancer Res., 1999, vol.5, pp. 41644174
Descrição da Invenção Problemas a serem resolvidos pela invenção
[005] Em comparação com um inibidor seletivo de EGFR ou HER2, espera-se que um inibidor dual para EGFR e HER2 seja mais eficaz, pois este último inibidor apresenta efeito mais forte em uma maior faixa de doenças por efeito sinergístico de inibição dual. Portanto, deseja-se um composto que iniba tanto o EGFR quanto o HER2.
Meios para resolver os problemas
[006] Na situação acima, os presentes inventores estudaram intensamente e, como resultado, descobriram que um derivado de quinazolina tendo um certo substituinte na posição 6 tem excelente atividade inibitória dual em um receptor de EGF e HER2.
[007] Isto é, a presente invenção refere-se a: (1) um composto representado pela fórmula geral (I): Fórmula química 1
Figure img0001
onde RX é um grupo representado pela fórmula: Fórmula química 2
Figure img0002
onde R1 é um átomo de hidrogênio, alquila opcionalmente substituída, alquenila opcionalmente substituída, arila opcionalmente substituída, ou um grupo heterocíclico contendo nitrogênio não- aromático opcionalmente substituído; Z é -O-, -N(R10)-, ou alquileno que pode ser interposto com - O- ou -N(R11)-; onde R10 e R11são independentemente um átomo de hidrogênio, alquila, acila, alquiloxicarbonila, alqueniloxicarbonila, ou aralquiloxicarbonila; R2é um átomo de hidrogênio, alquila opcionalmente substituída, alquenila opcionalmente substituída, alquinila opcionalmente substituída, cicloalquila opcionalmente substituída, arila opcionalmente substituída, ou heteroarila opcionalmente substituída; R19é alquila opcionalmente substituída, arila opcionalmente substituída, heteroarila opcionalmente substituída, ou um grupo heterocíclico não aromático opcionalmente substituído; R18é um átomo de hidrogênio, alquila opcionalmente substituída, alquenila opcionalmente substituída, ou alquinila opcionalmente substituída; W1é um grupo heterocíclico contendo nitrogênio não aromático opcionalmente substituído ou heteroarila opcionalmente substituída; R17é um átomo de hidrogênio, alquila opcionalmente substituída, alquenila opcionalmente substituída, ou um grupo heterocíclico contendo nitrogênio não-aromático opcionalmente substituído; R3 e R4são independentemente um átomo de hidrogênio, alquila opcionalmente substituída, alquenila opcionalmente substituída, alquinila opcionalmente substituída, alquilóxi opcionalmente substituído, alquenilóxi opcionalmente substituído, halogênio, hidróxi, mercapto, ou amina opcionalmente substituída,; X é -O-, -S-, -N(R12)-, ou alquileno que pode ser interposto com -O-, -S-, ou -N(R13)-; onde R12 e R13são independentemente um átomo de hidrogênio, alquila, acila, alquiloxicarbonila, alqueniloxicarbonila, ou aralquiloxicarbonila; e
[008] A é um grupo representado pela fórmula: Fórmula química 3
Figure img0003
onde R5 é um átomo de hidrogênio, halogênio, alquilóxi opcional-mente substituído, alquenilóxi opcionalmente substituído, alquinilóxi opcionalmente substituído, ou um grupo representado pela fórmula: -Y-R8 onde Y é -O-, -S-, -SO2-, ou alquileno que pode ser interposto com -O-, - S-, ou -N(R9)-, R8 é arila opcionalmente substituída ou heteroarila opcionalmente substituída; R9 é um átomo de hidrogênio, alquila, acila, alquiloxicarbonila, alqueniloxicarbonila, ou aralquiloxicarbonila; R6 e R7 são independentemente um átomo de hidrogênio, alquila opcionalmente substituída, alquenila opcionalmente substituída, alquinila opcionalmente substituída, alquilóxi opcionalmente substituído, alquenilóxi opcionalmente substituído, alquinilóxi opcionalmente substituído, halogênio, hidróxi, mercapto, ciano, ou amina opcionalmente substituída; R20 é alquila opcionalmente substituída, alquenila opcional-mente substituída, alquinila opcionalmente substituída, ou um grupo representado pela fórmula: Fórmula química 4
Figure img0004
onde R5, R6 e R7 são como definidos acima; Q é N ou CH2, seu sal farmaceuticamente aceitável, ou um solvato do mesmo.
[009] Mais particularmente, a presente invenção refere-se aos itens (2) a (20) a seguir. (2) O composto de acordo com o item (1), onde RXé um grupo representado pela fórmula: Fórmula química 5
Figure img0005
onde R1, R2, R18, R19, Z, eW1são como definidos no item (1), seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (3) O composto de acordo com o item (1) ou (2), onde R1é alquila opcionalmente substituída com um substituinte selecionado do grupo A de substituintes que consiste em hidróxi, heteroarila, carbóxi, amina opcionalmente substituída, um grupo heterocíclico contendo nitrogênio não aromático opcionalmente substituído, aminocarbonila opcionalmente substituída, e carbonila heterocíclico contendo nitrogênio não aromático opcionalmente substituído, ou um grupo heterocíclico contendo nitrogênio não aromático opcionalmente substituído com um substituinte selecionado do grupo B de substituintes que consiste em alquiloxicarbonila, aminocarbonila opcionalmente substituída, oxo, amino, carbóxi, ciano, cianoalquila, hidroxialquila, alquilcarbonilamino, alquilsulfonilamino, e aminocarbonilalquila, seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (4) O composto de acordo com qualquer um dos itens (1) a (3), onde R1é alquila substituída com amina opcionalmente substituída com um substituinte selecionado do grupo C de substituintes que consiste em alquila, alquenila, alquinila, arila opcionalmente substituída, aralquila, alquilóxi, hidroxialquila, hidroxialquiloxialquila, haloalquila, aminoalquila opcionalmente substituída com 1 ou 2 alquilas, alquilsulfonila, alquilsulfonilalquila, alquilcarbonila opcionalmente substituída com halogênio ou alquilóxi, alquiloxicarbonila, cicloalquila opcionalmente substituída, carboxialquila, aminocarbonilalquila opcionalmente substituída, aminocarboniloxialquila opcionalmente substituída, alquiloxialquila, alquiltioalquila, alquilcarbonilaminoalquila, alquilsulfonilaminoalquila, alquilsulfonila(alquila)aminoalquila, alquiloxi- carbonilalquila, alquiltio(hidroxi)alquila, cicloalquilalquila, cianoalquila, aminoalquilcarbonila opcionalmente substituída, heteroarila opcional-mentesubstituída, heteroarilalquila, hidroxialquiloxialquila, um grupo heterocíclico não aromático opcionalmente substituído, e alquila heterocíclica não aromática opcionalmente substituída, alquila substituída com um grupo heterocíclico contendo nitrogênio não aromático opcionalmente substituído com um substituinte selecionado do grupo D de substituintes que consiste em halogênio; arila; hidróxi; oxo; aminocarbonila opcionalmente substituída; alquiloxicarbonila; alquila opcionalmente substituída com um substitu- inte selecionado do grupo H de substituintes que consiste em aminocarbonila opcionalmente substituída, ciano, alquilóxi, alquilsulfo- nilamino, amino, carbóxi, alquiloxicarbonila, and hidróxi; alquilaminocar- bonila; carbóxi; ciano; alquilsulfonila; alquilcarbonila; alquenilcarbonila; alquilsulfonilalquilcarbonila; alquiloxialquilcarbonila; alquilcarbonila- mino; aminocarbonilóxi; um grupo heterocíclico contendo nitrogênio não aromático; e carbonila heterocíclico não aromático, ou um grupo heterocíclico contendo nitrogênio não aromático opcionalmente substituído com um substituinte selecionado do grupo B de substituintes, seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (5) O composto de acordo com qualquer um dos itens (1) a (4), onde Z é -O-, seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (6) O composto de acordo com o item (1) ou (2), onde R19é alquila opcionalmente substituída com um substituinte selecionado do grupo A de substituintes; arila opcionalmente substituída com um substituinte selecionado do grupo I de substituintes que consiste em alquiloxicar- bonila, aminocarbonila opcionalmente substituída, ciano, cianoalquila, hidroxialquila, e aminocarbonilalquila, ou heteroarila opcionalmente substituída com um substituinte selecionado do grupo I de substituintes; seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (7) O composto de acordo com qualquer um dos itens (1), (2), e (6), onde R19é alquila substituída com amina opcionalmente substituída com um substituinte selecionado do grupo C de substituintes; ou alquila substituída com um grupo heterocíclico contendo nitrogênio não aromático opcionalmente substituído com um substituinte selecionado do grupo D de substituintes; seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (8) O composto de acordo com o item (1) ou (2), onde W1é um grupo representado por um grupo heterocíclico contendo nitrogênio não aromático opcionalmente substituído com um substituinte selecionado do grupo J de substituintes que consiste em alquila, cianoalquila, hidroxialquila, aminocarbonilalquila, alquilóxi, alquiloxicarbonila, aminocarbonila opcionalmente substituída, e ciano; ou um grupo representado por heteroarila opcionalmente substituída com um substituinte selecionado do grupo J de substituintes; seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (9) O composto de acordo com qualquer um dos itens (1) a (8), onde R2é um átomo de hidrogênio, C1-C6 alquila opcionalmente substituída com halogênio, C2-C6 alquenila, C2-C6 alquinila, halogênio, ou fenila, seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (10) O composto de acordo com qualquer um dos itens (1) a (9), onde R2é C2-C4 alquinila, seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (11) O composto de acordo com qualquer um dos itens (1) a (10), onde um de R3 e R4é um átomo de hidrogênio, e o outro é um átomo de hidrogênio, alquilóxi opcionalmente substituído ou alquenilóxi opcionalmente substituído, seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (12) O composto de acordo com qualquer um dos itens (1) a (11), onde X é -NH-, seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (13) O composto de acordo com qualquer um dos itens (1) a (12), onde A é um grupo representado pela fórmula: Fórmula química 6
Figure img0006
onde R5é um átomo de hidrogênio ou halogênio; R6é halogênio ou alquinila; e R7é um átomo de hidrogênio, seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (14) O composto de acordo com qualquer um dos itens (1) a (12), onde A é um grupo representado pela fórmula: Fórmula química 7
Figure img0007
onde R5é alquilóxi opcionalmente substituído com um substituinte selecionado do grupo E de substituintes que consiste em carbóxi, alcoxioxicarbonila, cicloalquila, e aminocarbonila opcionalmente substituída; alquenilóxi opcionalmente substituído com um substituinte selecionado do grupo E de substituintes; ou alquinilóxi opcionalmente substituído com um substituinte selecionado do grupo E de substituintes; R6é alquinila opcionalmente substituída, alquilóxi opcionalmente substituído, ou halogênio; e R7é um átomo de hidrogênio, seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (15) O composto de acordo com qualquer um dos itens (1) a (12), onde A é um grupo representado pela fórmula: Fórmula química 8
Figure img0008
onde R5é um grupo representado pela fórmula: -Y-R8 onde Y é alquileno que pode ser interposto com -O-; R8é fenila opcionalmente substituída com um substituinte selecionado do grupo F de substituintes que consiste em halogênio, carbóxi, alquila, haloalquila, hidroxialquila, alquilóxi, alquiloxicarbonila, e amina opcionalmente substituída; piridila opcionalmente substituída com um substituinte selecionado do grupo F de substituintes; furila opcionalmente substituída com um substituinte selecionado do grupo F de substituintes; tienila opcionalmente substituída com um substituinte selecionado do grupo F de substituintes; tiazolila opcionalmente substituída com um substituinte selecionado do grupo F de substituintes; ou oxazolila opcionalmente substituída com um substituinte selecionado do grupo F de substituintes; R6é alquinila opcionalmente substituída, alquilóxi opcionalmente substituído, ou halogênio; e R7é um átomo de hidrogênio, seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (16) O composto de acordo com o item (1), onde RXé um grupo representado pela fórmula: Fórmula química 9
Figure img0009
onde R1é alquila substituída com amina opcionalmente substituída com alquila, hidroxialquila, alquilcarbonilaminoalquila ou um heterociclo não aromático; alquila substituída com um heterociclo contendo nitrogênio não aromático opcionalmente substituído com alquila, hidroxialquila ou alquilcarbonilamino; ou um grupo heterocíclico contendo nitrogênio não aromático substituído com hidroxialquila; e R2é C2-C4 alquinila; R3 e R4são ambos um átomo de hidrogênio; X é -NH-; e
[010] A é um grupo representado pela fórmula: Fórmula química 10
Figure img0010
onde R5é um grupo representado pela fórmula: -Y-R8 onde Y é C1-C3 alquileno que pode ser interposto com -O-; R8é fenila opcionalmente substituída com halogênio, ou piridila opcionalmente substituída com halogênio; R6é halogênio; e R7é um átomo de hidrogênio, seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (17) Uma composição farmacêutica contendo o composto definido em qualquer um dos itens (1) a (16) como ingrediente ativo. (18) Uma composição farmacêutica útila para o tratamento de câncer contendo o composto definido em qualquer um dos itens (1) a (16) como ingrediente ativo. (19) Um método para prevenir e/ou tratar um câncer, compreendendo administrar o composto de acordo com qualquer um dos itens (1) a (16), seus sal farmaceuticamente aceitável ou um solvato do mesmo. (20) Uso do composto de acordo com qualquer um dos itens (1) a (16), seu solvato farmaceuticamente aceitável ou um sal para produzir uma composição para prevenir e/ou tratar um câncer.
[011] Além disso, a presente invenção inclui as seguintes invenções como outro aspecto. (I) Um composto representado pela fórmula geral (I): Fórmula química 11
Figure img0011
onde RXé um grupo representado pela fórmula: Fórmula química 12
Figure img0012
onde R1é um átomo de hidrogênio, alquila opcionalmente substituída, alquenila opcionalmente substituída, ou um grupo heterocíclico contendo nitrogênio não-aromático opcionalmente substituído; Z é -O- ou -N(R10)-, ou alquileno que pode ser interposto com -O- ou -N(R11)-; R10 e R11são independentemente um átomo de hidrogênio, alquila, acila, alquiloxicarbonila, alqueniloxicarbonila, ou aralquiloxicarbonila; R2é um átomo de hidrogênio, alquila opcionalmente substituída, alquenila opcionalmente substituída, alquinila opcionalmente substituída, arila opcionalmente substituída, ou heteroarila opcionalmente substituída; R19é alquila opcionalmente substituída, arila opcionalmente substituída, heteroarila opcionalmente substituída, ou um grupo heterocíclico não aromático opcionalmente substituído; R18é um átomo de hidrogênio, alquila opcionalmente substituída, alquenila opcionalmente substituída, ou alquilnila opcionalmente substituída; W1é um grupo heterocíclico contendo nitrogênio não aromático opcionalmente substituído ou heteroarila opcionalmente substituída; R17é um grupo hidrogênio, alquila opcionalmente substituída, alquenila opcionalmente substituída, ou um grupo heterocíclico contendo nitrogênio não aromático opcionalmente substituído; R3 e R4são independentemente um átomo de hidrogênio, alquila opcionalmente substituída, alquenila opcionalmente substituída, alquinila opcionalmente substituída, alquilóxi opcionalmente substituído, alquenilóxi opcionalmente substituído, halogênio, hidróxi, mercapto, ou amina opcionalmente substituída; X é -O-, -S-, -N(R12)-, ou alquileno que pode ser interposto com -O-, -S-, ou -N(R13)-; onde R12 e R13são independentemente um átomo de hidrogênio, alquila, acila, alquiloxicarbonila, alqueniloxicarbonila, ou aralquiloxicarbonila; e
[012] A é um grupo representado pela fórmula: Fórmula química 13
Figure img0013
onde R5é um átomo de hidrogênio, halogênio, alquilóxi opcionalmente substituído, alquenilóxi opcionalmente substituído, alquinilóxi opcionalmente substituído, ou um grupo representado pela fórmula: -Y-R8 onde Y é -O-, -S-, ou alquileno que pode ser interposto com -N(R9)-; R8é arila opcionalmente substituída, ou heteroarila opcionalmente substituída; R9é um átomo de hidrogênio, alquila, acila, alquiloxicarbonila, alqueniloxicarbonila, ou aralquiloxicarbonila; R6 e R7são independentemente um átomo de hidrogênio, alquila opcionalmente substituída, alquenila opcionalmente substituída, alquinila opcionalmente substituída, alquilóxi opcionalmente substituído, alquenilóxi opcionalmente substituído, alquinilóxi opcionalmente substituído, halogênio, hidróxi, mercapto, ou amina opcionalmente substituída; R20é alquila opcionalmente substituída, alquenila opcionalmente substituída, alquinila opcionalmente substituída, ou um grupo representado pela fórmula: Fórmula química 14
Figure img0014
onde R5, R6 e R7são como definidos acima; Q é N ou CH2, seu sal farmaceuticamente aceitável, ou um solvato do mesmo.
[013] Mais particularmente, a presente invenção refere-se aos itens (II) a (XV) a seguir. (II) Um composto de acordo com o item (I), onde RXé um grupo representado pela fórmula: Fórmula química 15
Figure img0015
onde R1, R2, R18, R19, Z, e W1são como definidos no item (I), seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (III) O composto de acordo com o item (I) ou (II), onde R1é alquila opcionalmente substituída com um substituinte selecionado do grupo A' de substituintes que consiste em hidróxi, amina opcionalmente substituída, um grupo heterocíclico contendo nitrogênio não aromático opcionalmente substituído, aminocarbonila opcionalmente substituída, e carbonila heterocíclico contendo nitrogênio não aromático opcionalmente substituído, ou um grupo heterocíclico contendo nitrogênio não aromático opcionalmente substituído com um substituinte selecionado do grupo B' de substituintes que consiste em alquiloxicarbonila, aminocarbonila opcionalmente substituída, ciano, cianoalquila, hidroxialquila, e aminocarbonilalquila, seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (IV) O composto de acordo com qualquer um dos itens (I) a (III), onde R1é alquila opcionalmente substituída com amino substituído com um substituinte selecionado do grupo C' de substituintes que consiste em alquila, alquinila, alquilsulfonilalquila, hidroxialquila, alquilcarbonila opcionalmente substituída com halogênio, alquiloxicar- bonila, cicloalquila, opcionalmente substituída com aminocarbonilal- quila, aminocarboniloxialquila opcionalmente substituída, alquiloxial- quila, cicloalquilalquila, cianoalquila, e aminoalquilcarbonila opcional-mentesubstituída, ou alquila substituída com um grupo heterocíclico contendo nitrogênio não aromático opcionalmente substituído com um substituinte selecionado de um grupo D' de substituintes que consiste em hidróxi; oxo; aminocarbonila opcionalmente substituída; alquiloxicarbonila; alquila opcionalmente substituída com um substituinte selecionado do grupo H' de substituintes que consiste em aminocarbonila opcional-mentesubstituída, ciano, alquilóxi, e hidróxi; alquilaminocarbonila; ciano; alquilsulfonila; alquilcarbonila; alquenilcarbonila; alquilsulfonilal- quilcarbonila; alquiloxialquilcarbonila; alquilcarbonilamino; e carbonila heterocíclico não aromático, seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (V) O composto de acordo com o item (I) ou (II), onde R19é alquila opcionalmente substituída com um substituinte selecionado do grupo A' de substituintes, arila opcionalmente substituída com um substituinte selecionado do grupo I' de substituintes que consiste em alquiloxicarbonila, aminocarbonila opcionalmente substituída, ciano, cianoalquila, hidroxialquila, e aminocarbonilalquila, ou heteroarila substituída com um substituinte selecionado do grupo I' de substituintes, seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (VI) O composto de acordo com qualquer um dos itens (I), (II) e (V), onde R19é alquila substituída com amina opcionalmente substituída com um substituinte selecionado do grupo C' de substituintes, ou alquila substituída com um grupo heterocíclico contendo nitrogênio não aromático opcionalmente substituído com um substituinte selecionado do grupo D' de substituintes, seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (VII) O composto de acordo com o item (I) ou (II), onde W1é um grupo representado por um grupo heterocíclico contendo nitrogênio não aromático opcionalmente substituído com um substituinte selecionado do grupo J' de substituintes que consiste em alquila, cianoalquila, hidroxialquila, aminocarbonilalquila, alquilóxi, alquiloxicarbonila, aminocarbonila opcionalmente substituída, e ciano, ou um grupo representado por heteroarila opcionalmente substituída com um substituinte selecionado do grupo J' de substituintes, seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (VIII) O composto de acordo com qualquer um dos itens (I) a (VII), onde R2é um átomo de hidrogênio, C1-C6 alquila opcionalmente substituída com halogênio, C2-C6 alquenila, C2-C6 alquinila, halogênio, ou fenila, seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (IX) O composto de acordo com qualquer um dos itens (I) a (VIII), onde um de R3 e R4são um átomo de hidrogênio, e o outro é um átomo de hidrogênio, alquilóxi opcionalmente substituído ou alquenilóxi opcionalmente substituído, seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (X) O composto de acordo com qualquer um dos itens (I) a (IX), onde X é -NH-, seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (XI) O composto de acordo com qualquer um dos itens (I) a (IX), onde A é um grupo representado pela fórmula: Fórmula química 16
Figure img0016
onde R5é um átomo de hidrogênio ou halogênio; R6é halogênio ou alquinila; e R7é um hidrogênio, seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (XII) O composto de acordo com qualquer um dos itens (I) a (IX), onde A é um grupo representado pela fórmula: Fórmula química 17
Figure img0017
onde R5é alquilóxi opcionalmente substituído com um substituinte selecionado do grupo E' de substituintes que consiste em carbóxi, alquiloxicarbonila, cicloalquila, e aminocarbonila opcionalmente substituída, alquenilóxi opcionalmente substituído com um substituinte selecionado do grupo E' de substituintes, ou alquinilóxi opcionalmente substituído com um substituinte selecionado do grupo E' de substituintes; R6é alquinila opcionalmente substituída, alquilóxi opcionalmente substituído, ou halogênio; e R7é um átomo de hidrogênio, seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (XIII) O composto de acordo com qualquer um dos itens (I) a (IX), onde A é um grupo representado pela fórmula: Fórmula química 18
Figure img0018
onde R5é um grupo representado pela fórmula: -Y-R8 onde Y é alquileno que pode ser interposto com -O-; R8é fenila opcionalmente substituída com um substituinte selecionado do grupo F' de substituintes que consiste em halogênio, carbóxi, alquila, haloalquila, hidroxialquila, alquilóxi, alquiloxicarbonila, e amina opcionalmente substituída; piridila opcionalmente substituída com um substituinte selecionado do grupo F' de substituintes; furila opcionalmente substituída com um substituinte selecionado de um grupo F' de substituintes; tienila opcionalmente substituída com um substituinte selecionado de um grupo F' de substituintes; tiazolila opcionalmente substituída com um substituinte selecionado de um grupo F' de substituintes; ou oxazolila opcionalmente substituída com um substituinte selecionado de um grupo F' de substituintes; R6é alquinila opcionalmente substituída, alquilóxi opcionalmente substituído, ou halogênio; e R7é um átomo de hidrogênio, seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (XIV) Uma composição farmacêutica contendo o composto definido em qualquer um dos itens (I) a (XIII) como ingrediente ativo. (XV) Uma composição farmacêutica útila para o tratamento de câncer contendo o composto definido em qualquer um dos itens (I) a (XIII) como um ingrediente ativo. (XVI) Um método para prevenir e/ou tratar um câncer, compreendendo administrar o composto definido em qualquer um dos itens (I) a (XIII), seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (XVII) Uso do composto definido em qualquer um dos itens (I) a (XIII), seu sal farmaceuticamente aceitável, ou um solvato do mesmo para produzir uma composição para prevenir e/ou um câncer.
[014] Ainda um outro aspecto da presente invenção inclui as seguintes invenções. (i) um composto representado pela fórmula geral (I'): Fórmula química 19
Figure img0019
onde R1é um átomo de hidrogênio, alquila opcionalmente substituída, alquenila opcionalmente substituída, ou um grupo heterocíclico contendo nitrogênio não aromático opcionalmente substituído; Z é -O- ou -N(R10)-, ou alquileno que pode ser interposto com -O- ou -N(R11)-; R10 e R11são independentemente um átomo de hidrogênio, alquila, acila, alquiloxicarbonila, alqueniloxicarbonila, ou aralquiloxicarbonila; R2é um átomo de hidrogênio, alquila opcionalmente substituída, alquenila, alquinila, arila opcionalmente substituída, ou heteroarila opcionalmente substituída, ou um grupo representado por -C(R2) = N-Z-R1é um grupo representado pela fórmula: Fórmula química 20
Figure img0020
onde R17é um átomo de hidrogênio, alquila opcionalmente substituída, alquenila opcionalmente substituída, ou um grupo heterocíclico contendo nitrogênio não-aromático opcionalmente substituído; R3 e R4são independentemente um átomo de hidrogênio, alquila opcionalmente substituída, alquenila opcionalmente substituída, alquinila opcionalmente substituída, alquilóxi opcionalmente substituído, alquenilóxi opcionalmente substituído, halogênio, hidróxi, mercapto ou amina opcionalmente substituída; X é -O-, -S-, ou -N(R12)-, ou alquileno que pode ser interposto com -O-, -S-, ou -N(R13)-; onde R12 e R13são independentemente um átomo de hidrogênio, alquila, acila, alquiloxicarbonila, alqueniloxicarbonila, ou aralquiloxicarbonila; e
[015] A é um grupo representado pela fórmula: Fórmula química 21
Figure img0021
onde R5é um átomo de hidrogênio, halogênio, alquilóxi opcionalmente substituído, alquenilóxi opcionalmente substituído, alquinilóxi opcionalmente substituído, ou um grupo representado pela fórmula: -Y-R8 onde Y é -O-, -S-, ou alquileno que pode ser interposto com -N(R9)-; R8é arila opcionalmente substituída, ou heteroarila opcionalmente substituída; R9é um átomo de hidrogênio, alquila, acila, alquiloxicarbonila, alqueniloxicarbonila, ou aralquiloxicarbonila; R6 e R7são independentemente um átomo de hidrogênio, alquila opcionalmente substituída, alquenila opcionalmente substituída, alquinila opcionalmente substituída, alquilóxi opcionalmente substituído, alquenilóxi opcionalmente substituído, alquinilóxi opcionalmente substitu-ído, halogênio, hidróxi, mercapto, ou amina opcionalmente substituída, seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (ii) O composto de acordo com o item (i), onde R1é alquila opcionalmente substituída com um substituinte selecionado do grupo A'' de substituintes que consiste em amina opcionalmente substituída, e um grupo heterocíclico contendo nitrogênio não aromático opcionalmente substituído, ou um grupo heterocíclico contendo nitrogênio não aromático opcionalmente substituído com um substituinte selecionado do grupo B'' de substituintes que consiste em alquiloxicarbonila, aminocarbonila opcionalmente substituída, e ciano, seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (iii) O composto de acordo com o item (i) ou (ii), onde R1é alquila substituída com amina opcionalmente substituída com um substi- tuinte selecionado do grupo C'' de substituintes que consiste em alquila, alquilsulfonilalquila, alquilcarbonila opcionalmente substituído com halogê- nio, alquiloxicarbonila, cicloalquila, aminocarbonilalquila opcionalmente substituída, aminocarboniloxialquila opcionalmente substituída, alquiloxial- quila, e aminoalquilcarbonila opcionalmente substituído, ou alquila substituída com um grupo heterocíclico contendo nitrogênio não aromático opcionalmente substituído com um substituinte selecionado do grupo D'' de substituintes que consiste em oxo, aminocarbonila opcionalmente substituída, alquiloxicarbonila, alquila opcionalmente substituída com ciano ou alquilóxi, ciano, alquilsulfonila, alquilcarbonila, alquenilcarbonila, e alquilsulfonilalquilcarbonila, seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (iv) O composto de acordo com qualquer um dos itens (i) a (iii), onde um de R3 e R4é um átomo de hidrogênio, e o outro é um átomo de hidrogênio, alquilóxi opcionalmente substituído ou alquenilóxi opcionalmente substituído, seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (v) O composto de acordo com qualquer um dos itens (i) a (iv), onde X é -NH-, seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (vi) O composto de acordo com qualquer um dos itens (i) a (v), onde A é um grupo representado pela fórmula: Fórmula química 22
Figure img0022
onde R5é um átomo de hidrogênio ou halogênio; R6é halogênio ou alquinila; e R7é um átomo de hidrogênio, seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (vii) O composto de acordo com qualquer um dos itens (i) a (vi), onde A é um grupo representado pela fórmula: Fórmula química 23
Figure img0023
onde R5é alquilóxi opcionalmente substituído com um substituinte selecionado do grupo E'' de substituintes que consiste em carbóxi, alquiloxicarbonila, e aminocarbonila opcionalmente substituída, alquenilóxi opcionalmente substituído com um substituinte selecionado de um grupo E'' de substituintes, ou alquinilóxi opcionalmente substituído com um substituinte selecionado de um grupo E'' de substituintes; R6é alquinila opcionalmente substituída, alquilóxi opcionalmente substituído, ou halogênio; e R7é um átomo de hidrogênio, seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (viii) O composto de acordo com qualquer um dos itens (i) a (vii), onde A é um grupo representado pela fórmula: Fórmula química 24
Figure img0024
onde R5é um grupo representado pela fórmula: -Y-R8 onde Y é alquileno que pode ser interposto com -O-; R8é fenila opcionalmente substituída com um substituinte selecionado do grupo F'' de substituintes que consiste em halogênio, carbóxi, alquila, haloalquila, hidroxialquila, alquilóxi, alquiloxicarbonila, e amina opcionalmente substituída; piridila opcionalmente substituída com um substituinte selecionado de um grupo F'' de substituintes; furila opcionalmente substituída com um substituinte selecionado de um grupo F'' de substituintes; tienila opcionalmente substituída com um substituinte selecionado de um grupo F'' de substituintes; tiazolila opcionalmente substituída com um substituinte selecionado de um grupo F'' de substituintes; ou oxazolila opcionalmente substituída com um substituinte selecionado de um grupo F'' de substituintes; R6é alquinila opcionalmente substituída, alquilóxi opcionalmente substituído, ou halogênio; e R'é um átomo de hidrogênio, seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (ix) Uma composição farmacêutica contendo o composto definido em qualquer um dos itens (i) a (viii) como ingrediente ativo. (x) Uma composição farmacêutica útila para o tratamento de câncer contendo o composto definido em qualquer um dos itens (i) a (viii) como um ingrediente ativo. (xi) Um método para prevenir e/ou tratar um câncer, compreendendo administrar o composto definido em qualquer um dos itens (i) a (viii), seu sal farmaceuticamente aceitável, ou um solvato do mesmo. (xii) Uso do composto definido em qualquer um dos itens (i) a (viii), seu sal farmaceuticamente aceitável, ou um solvato do mesmo para produzir uma composição para prevenir e/ou tratar um câncer.
[016] Conforme usado neste relatório, "halogênio"significa flúor, cloro, bromo ou iodo. Flúor, cloro e bromo são preferidos.
[017] Conforme usado neste relatório, "alquila" que é usado isolado ou está em combinação com outro termo inclui um grupo hidrocarboneto monovalente de cadeia reta ou ramificada tendo 1 a 10 átomos de carbono. Exemplos incluem metila, etila, n-propila, isopropila, n-butila, isobutila, sec-butila, tert-butila, n-pentila, isopentila, neo-pentila, n-hexila, isohexila, n-heptila, n-octila, n-nonanila, e n-decanila. Exemplos preferidos incluem C1-C10 alquila. Outros exemplos preferidos incluem C1-C6 alquila. Exemplos mais preferidos incluem C1-C4 alquila.
[018] Conforme usado neste relatório, o termo "haloalquila" que é usado isolado ou está em combinação com outro termo inclui "alquila" que é substituído com "halogênio"nas posições 1 a 8, de preferência nas posições 1 a 5. Exemplos incluem trifluormetila, triclorometila, difluoretila, trifluoretila, dicloroetila, e tricloroetila. Exemplos preferidos incluem C1-C6 alquila que é substituído com "halogênio"nas posições 1 a 5.. Particularmente, C1-C3 alquila substituída com "halogênio"nas posições 1 a 3 é preferido. Exemplos mais preferidos incluem trifluormetila.
[019] Conforme usado neste relatório, "alquilsulfonila" inclui metilsulfonila, etilsulfonila, e propilsulfonila. Exemplos preferidos incluem C1-C6 alquilsulfonila. Particularmente, C1-C3 alquilsulfonila é preferido.
[020] Conforme usado neste relatório, exemplos de "alquilsulfonilalquila" incluem metilsulfonilmetila, metilsulfoniletila, metilsulfonilpropila, metilsulfonilbutila, e metilsulfonilpropila. Exemplos preferidos incluem C1- C6 alquilsulfonila C1-C6 alquila. Particularmente, C1-C3 alquilsulfonila C1-C4 alquila é preferida.
[021] Conforme usado neste relatório, exemplos de "alquilóxi"incluem metilóxi, etilóxi, n-propilóxi, isopropilóxi, n-butilóxi, isobutilóxi, sec-butilóxi, ter-butilóxi, n-pentilóxi, n-hexilóxi, n-heptilóxi, n-octilóxi, n- nonanilóxi, e n-decanilóxi. Exemplos preferidos incluem C1-C6 alquilóxi. Particularmente, C1-C3 alquilóxi é preferido.
[022] Conforme usado neste relatório, exemplos de "alquiloxialquila" incluem metiloximetila, metiloxietila, metiloxipropila, etiloximetila, etiloxietila, e etiloxipropila. Exemplos preferidos incluem C1-C6 alquilóxi C1-C6 alquila. Particularmente, C1-C3 alquilóxi C1-C4 alquila é preferida.
[023] Conforme usado neste relatório, exemplos de "alquiloxicarbonila" incluem metiloxicarbonila, etiloxicarbonila, n- propiloxicarbonila, isopropiloxicarbonila, n-butiloxicarbonila, t- butiloxicarbonila, e n-pentiloxicarbonila. Exemplos preferidos incluem C1-C6 alquiloxicarbonila. Particularmente, C1-C3 alquiloxicarbonila é preferido.
[024] Conforme usado neste relatório, exemplos de "alquilcarbonila" incluem metilcarbonila, etilcarbonila, n-propilcarbonila, isopropilcarbonila, n-butilcarbonila, t-butilcarbonila, e n-pentilcarbonila. Exemplos preferidos incluem C1-C6 alquilcarbonila. Particularmente, C1-C3 alquilcarbonila é preferido.
[025] Conforme usado neste relatório, exemplos de "haloalquilóxi"incluem trifluormetilóxi, triclorometilóxi, difluoretilóxi, trifluoretilóxi, dicloroetilóxi, e tricloroetilóxi. Exemplos preferidos incluem halo C1-C6 alquilóxi. Particularmente, halo C1-C3 alquilóxi é preferido. Exemplos mais preferidos incluem trifluormetilóxi.
[026] Conforme usado neste relatório, exemplos de "aminocarbonilalquila" incluem aminocarbonilmetila, aminocarboniletila, aminocarbonilpropila, e aminocarbonilbutila. Exemplos preferidos incluem aminocarbonila C1-C6 alquila. Particularmente, aminocarbonila C1-C3 alquila é preferido.
[027] Conforme usado neste relatório, exemplos de "aminocarbonilalquilóxi"incluem aminocarbonilmetilóxi, aminocarbo- niletilóxi, aminocarbonilpropilóxi, e aminocarbonilbutilóxi. Exemplos preferidos incluem aminocarbonila C1-C6 alquilóxi. Particularmente, aminocarbonila C1-C3 alquilóxi é preferido.
[028] Conforme usado neste relatório, exemplos de "hidroxialquila" incluem hidroximetila, hidroxietila, hidroxipropila, e hidroxibutila. Exemplos preferidos incluem hidroxi C1-C6 alquila. Particularmente, hidróxi C1-C3 alquila é preferido.
[029] Conforme usado neste relatório, exemplos de "alquiltio" incluem metiltio, etiltio, propiltio, e butiltio. Exemplos preferidos incluem C1-C6 alquiltio. Particularmente, C1-C3 alquiltio é preferido.
[030] Conforme usado neste relatório, o "alquileno" que é usado isolado ou em combinação com outro termo inclui um grupo hidrocarboneto divalente de cadeia reta ou ramificada tendo 1 a 4 átomos de carbono. Exemplos incluem metileno, etileno, propileno, e butileno. Exemplos preferidos incluem C1-C3 alquileno. Particularmente, C1-C2 alquileno é preferido.
[031] O "alquileno que pode ser interposto com -O- ou -N(R11)-" em Z inclui -CH2-O-, -O-CH2-, -CH2-N(R11)-, -N(R11)-CH2-, -(CH2)2-O-, -O- (CH2)2-, -(CH2)2-N(R11)-, e -N(R11)-(CH2)2-. Particularmente, -O-CH2-, - N(R11)-CH2-, -O-(CH2)2-, e -N(R11)-(CH2)2- são preferidos.
[032] O "alquileno que pode ser interposto com -O-, -S-, ou - N(R12)-" em X inclui -CH2-O-, -O-CH2-, -CH2-S-, -S-CH2-, -CH2-N(R12)-, -N(R12)-CH2-, -(CH2)2-O-, -O-(CH2)2-, -(CH2)2-S-, -S-(CH2)2-, -(CH2)2- N(R12)-, e -N(R12)-(CH2)2-.
[033] O "alquileno que pode ser interposto com -O-, -S-, ou -N(R9)- " em Y inclui -CH2-O-, -O-CH2-, -CH2-S-, -S-CH2-, -CH2-N(R9)-, -N(R9)- CH2-, -(CH2)2-O-, -O(CH2)2-, -(CH2)2-S-, -S-(CH2)2-, -(CH2)2-N(R9)-, - N(R9)-(CH2)2-, e -O-CH(CH3)-.
[034] Conforme usado neste relatório, "cicloalquila" que é usada isolada ou em combinação com outro termo inclui cicloalquila tendo 3 a 8 átomos de carbono. Exemplos incluem ciclopropila, ciclobutila, ciclopentila, ciclohexila, cicloheptila, e ciclooctila. Exemplos preferidos incluem C5-C6 cicloalquila.
[035] Conforme usado neste relatório, "alquenila" inclui um hidrocarboneto monovalente de cadeia reta ou ramificada tendo 2 a 8 átomos de carbono e tendo 1 ou 2 ou mais ligações duplas. A alquenila pode ter uma ligação tripla em uma cadeia. Exemplos incluem vinila, alila, 1-propenila, 2-propenila, e vários isômeros butenílicos. Exemplos preferidos incluem C2-C6 alquenila. Outros exemplos preferidos incluem C2-C4 alquenila.
[036] Conforme usado neste relatório, exemplos de "alquenilóxi"incluem vinilóxi, alilóxi, 1-propenilóxi, 2-propenilóxi, e vários butenilóxis. Exemplos preferidos incluem C2-C6 alquenilóxi. Particularmente, C2-C4 alquenilóxi é preferido.
[037] Conforme usado neste relatório, exemplos de "alqueniloxicarbonila" incluem viniloxicarbonila, aliloxicarbonila, 1- propeniloxicarbonila, 2-propeniloxicarbonila, e várias buteniloxicarbonilas. Exemplos preferidos incluem C2-C6 alqueniloxicarbonila. Particularmente, C2-C4 alqueniloxicarbonila é preferida.
[038] Conforme usado neste relatório, "alquinila" inclui um grupo hidrocarboneto monovalente de cadeia reta ou ramificada tendo 2 a 8 átomos de carbono e tendo 1 ou 2 ou mais ligações triplas. Exemplos incluem etinila, 1-propinila, 2-propinila, 1-butinila, 2-butinila, 3-butinila, 1-pentinila, 2-pentinila, e vários isômeros pentinílicos. Exemplos preferidos incluem C2-C6 alquinila. Outros exemplos preferidos incluem C2-C4 alquinila.
[039] Conforme usado neste relatório, exemplos de "alquinilóxi"incluem etinilóxi, propinilóxi, butinilóxi, e pentinilóxi. Exemplos preferidos incluem C2-C6 alquinilóxi. Particularmente, C2-C4 alquinilóxi é preferido.
[040] Conforme usado neste relatório, "arila" que é usada isolada ou em combinação com outro termo inclui um hidrocarboneto aromático cíclico fundido ou monocíclico. Exemplos incluem fenila, 1-naftila, 2- naftila, e antrila. Fenila, 1-naftila, e 2-naftila são preferidos. Particularmente, fenila é preferido.
[041] Conforme usado neste relatório, "aralquila" inclui "alquila"substituído com um ou duas ou mais "arila", e estas podem ser substituídos em todas as posições possíveis. Exemplos incluem benzila, feniletila (por exemplo, 2-feniletila, etc.), fenilpropila (por exemplo, 3- fenilpropila, etc.), naftilmetila (por exemplo, 1-naftilmetila, 2-naftilmetila, etc.), e antrilmetila (por exemplo, 9-antrilmetila, etc.). Exemplos preferidos incluem benzila, e feniletila.
[042] Conforme usado neste relatório, exemplos de "aralquilóxi"incluem benzilóxi, feniletilóxi (por exemplo 2-feniletilóxi, etc.), fenilpropilóxi (por exemplo 3-fenilpropilóxi, etc.), naftilmetilóxi (por exemplo 1-naftilmetila, 2-naftilmetilóxi, etc.), antrilmetilóxi (por exemplo 9-antrilmetilóxi, etc.). Exemplos preferidos incluem benzilóxi, e feniletilóxi.
[043] Conforme usado neste relatório, exemplos de "aralquiloxicarbonila" incluem benziloxicarbonila, feniletiloxicarbonila (por exemplo 2-feniletiloxicarbonila, etc.), fenilpropiloxicarbonila (por exemplo 3-fenilpropiloxicarbonila, etc.), naftilmetiloxicarbonila (por exemplo 1-naftilmetila, 2-naftilmetiloxicarbonila, etc.), antrilmetiloxicar- bonila (por exemplo 9-antrilmetiloxicarbonila, etc.). Exemplos preferidos incluem benziloxicarbonila, e feniletiloxicarbonila.
[044] Conforme usado neste relatório, o termo "grupo heterocíclico não aromático"que é usado isolado ou em combinação com outro termo inclui um anel não aromático de 5 a 7 membros contendo um ou mais de um átomo de oxigênio, um átomo de enxofre ou um átomo de nitrogênio arbitrariamente selecionados em um anel, e um grupo derivado de um anel no qual um ou mais outros "grupos heterocíclicos não aromáticos"ou "heteroarilas"estão fundidos. Exemplos incluem pirrolidinila (por exemplo 1-pirrolidinila, 2-pirolidinila), pirrolinila (por exemplo 3-pirrolinila), imidazolidinila (por exemplo 2-imidazolidinila), imidazolinila (por exemplo imidazolinila), pirazolidinila (por exemplo 1- pirazolidinila, 2-pirazolidinila), pirazolinila (por exemplo pirazolinila), piperidila (por exemplo piperidino, 2-piperidila), piperazinila (por exemplo 1-piperazinila, 2-piperazinila), indolinila (por exemplo 1- indolinila), isoindolinila (por exemplo isoindolinila), morfolinila (por exemplo morfolino, 2-morfolinila, 3-morfolinila), tetrahidrofuranila, dihidropiranila, tetrahidropiranila, dioxolanila, tetrahidrotienila, dihidrotiopiranila, tetrahidrotiofuranila, decahidroisoquinolinila, azepinila, oxepinila, dihidrooxepinila, tetrahidrooxepinila, oxepanila, 4, 5, 6, 7- tetrahidrotieno[3, 2]piridila, 2-oxa-5-aza-biciclo[2.2.1]hepta-5-ila, e hexahidropirazila[2.1-b][1, 3]ozadin-8-ila.
[045] Como o "grupo heterocíclico não aromático"em R19, pirrodilinila (por exemplo 1-pirrodilinila, 2-pirrolidinila), piperidila (por exemplo piperidino, 2-piperidila), piperazinila (por exemplo 1- piperazinila), morfolinila (por exemplo morfolino, 3-morfolinila), e tetrahidrofuranila são preferidas.
[046] Conforme usado neste relatório, o termo "grupo heterocíclico contendo nitrogênio não aromático"que é usado isolado, ou em combinação com outro termo inclui um anel não aromático de 4 a 7 membros contendo pelo menos um átomo de nitrogênio em um anel e, ainda opcionalmente, contendo um ou mais átomos arbitrariamente selecionados de um átomo de oxigênio e um átomo de enxofre em um anel, ou um grupo derivado de um anel no qual dois ou mais deles estão fundidos. Exemplos incluem azetidinila (por exemplo 1-azetidinila, 2- azetidinila, 3-azetidinila), pirrolidinila (por exemplo 1-pirrolidinila, 2- pirrolidinila, 3-pirrolidinila), pirrolinila (por exemplo 3-pirrolinila), imidazolidinila (por exemplo 2-imidazolidinila), imidazolinila (por exemplo imidazolinila), pirazolidinila (por exemplo 1-pirazolidinila, 2- pirazolidinila), pirazolinila (por exemplo pirazolinila), piperidila (por exemplo piperidino, 2-piperidila, 3-piperidila, 4-piperidila), piperazinila (por exemplo 1-piperazinila, 2-piperazinila), indolinila (por exemplo 1- indolinila), isoindolinila (por exemplo isoindolinila), morfolinila (por exemplo morfolino, 2-morfolinila, 3-morfolinila), 1, 4-tiazinila (por exemplo 1, 4-tiazin-1-ila, 1, 4-tiazin-2-ila), tiomorfolinila (por exemplo 1- tiomorfolinila, 2-tiomorfolinila), decahidroisoquinolila (por exemplo 2- decahidroisoquinolila), azepinila (por exemplo 1-azepinila), diazepinila, 4, 5, 6, 7-tetrahidrotieno[3, 2]piridila, 2-oxa-5-aza-biciclo[2.2.1]hept-5-ila, e hexahidropirazila[2.1-b][1, 3]oxazin-8-ila.
[047] Como o "grupo heterocíclico contendo nitrogênio não aromático"em R1 e R17, azetidinila (por exemplo 1-azetidinila, 2- azetidinila, 3-azetidinila), pirrolidinila (por exemplo 1-pirrolidinila, 2- pirrolidinila, 3-pirrolidinila), e piperidila (por exemplo piperidino, 2- piperidila, 3-piperidila, 4-piperidila) são preferidas.
[048] Como o "grupo heterocíclico contendo nitrogênio não aromático"em W1, azetidinila (por exemplo 1-azetidinila, 2-azetidinila, 3-azetidinila), pirrolidinila (por exemplo 1-pirrolidinila, 2-pirrolidinila, 3- pirrolidinila), piperidila (por exemplo piperidino, 2-piperidila, 3-piperidila, 4-piperidila), piperazinila (por exemplo 1-piperazinila), e morfolinila (por exemplo morfolino, 3-morfolinila) são preferidas.
[049] Como o "grupo heterocíclico contendo nitrogênio não aromático"no grupo A de substituintes, pirrolidinila (por exemplo 1- pirrolidinila, 2-pirrolidinila, 3-pirrolidinila), piperidila (por exemplo piperidino, 2-piperidila, 3-piperidila, 4-piperidila), piperazinila (por exemplo 1-piperazinila, 2-piperazinila), morfolinila (por exemplo morfolino, 2-morfolinila, 3-morfolinila), tiomorfolinila (por exemplo 1- tiomorfolinila, 2-tiomorfolinila), decahidroisoquinolila (por exemplo 2- decahidroisoquinolila), azepinila (por exemplo 1-azepinila), diazepinila, 4, 5, 6, 7-tetrahidrotieno[3, 2]piridila, 2-oxa-5-aza-biciclo[2.2.1]hept-5-ila, e hexahidropirazila[2.1-b][1, 3]oxazin-8-ila são preferidos.
[050] Conforme usado neste relatório, "heteroarila" que é usado isolado, ou em combinação com outro termo inclui um grupo aromático de 5 a 6 membros contendo um ou mais de um átomo de oxigênio, um átomo de enxofre e um átomo de nitrogênio arbitrariamente selecionado em um anel. Este pode ser fundido com a "cicloalquila", a "arila", o "grupo heterocíclico não aromático", ou outro heteroarila em todas as posições possíveis. Quando heteroarila é qualquer um de um monociclo e um ciclo fundido, ele pode se ligar em todas as posições possíveis. Exemplos incluem pirrolila (por exemplo 1-pirrolila, 2-pirrolila, 3-pirrolila), furila (por exemplo 2-furila, 3-furila), tienila (por exemplo 2-tienila, 3- tienila), imidazolila (por exemplo 2-imidazolila, 4-imidazolila), pirazolila (por exemplo 1-pirazolila, 3-pirazolila), isotiazolila (por exemplo 3- isotiazolila), isooxazolila (por exemplo 3-isooxazolila), oxazolila (por exemplo 2-oxazolila), tiazolila (por exemplo 2-tiazolila, 5-tiazolila), piridila (por exemplo 2-piridila, 3-piridila, 4-piridila), pirazinila (por exemplo 2-pirazinila), pirimidinila (por exemplo 2-pirimidinila, 4- pirimidinila), piridazinila (por exemplo 3-piridazinila), triazolila, tetrazolila (por exemplo 1H-tetrazolila), oxadiazolila (por exemplo 1, 3, 4- oxadiazolila), tiadiazolila (por exemplo 1, 3, 4-tiadiazolila), indolidinila (por exemplo 2-indolidinila, 6-indolidinila), isoindolila (por exemplo 2- isoindolila), indolila (por exemplo 1-indolila, 2-indolila, 3-indolila), indazolila (por exemplo 3-indazolila), purinila (por exemplo 8-purinila), quinolizinila (por exemplo 2-quinolizinila), isoquinolila (por exemplo 3- isoquinolila), quinolila (por exemplo 2-quinolila, 5-quinolila), ftalazinila (por exemplo 1-ftalazinila), naftiridinila (por exemplo 2-naftiridinila), quinolanila (por exemplo 2-quinolanila), quinazolinila (por exemplo 2- quinazolinila), cinolinila (por exemplo 3-cinolinila), pteridinila (por exemplo 2-pteridinila), carbazolila (por exemplo 2-carbazolila, 4- carbazolila), fenantridinila (por exemplo 2-fenantridinila, 3- fenantridinila), acridinila (por exemplo 1-acridinila, 2-acridinila), dibenzofuranila (por exemplo 1-dibenzofuranila, 2-dibenzofuranila), benzoimidazolila (por exemplo 2-benzoimidazolila), benzoisooxazolila (por exemplo 3-benzoisooxazolila), benzooxazolila (por exemplo 2- benzooxazolila), benzooxadiazolila (por exemplo 4-benzooxadiazolila), benzoisotiazolila (por exemplo 3-benzoisotiazolila), benzotiazolila (por exemplo 2-benzotiazolila), benzofurila (por exemplo 3-benzofurila), benzotienila (por exemplo 2-benzotienila), 4, 5-dihidronafto[1, 2- d]tiazolila, 4H-cromeno[4, 3-d]tiazolila, 4H-tiocromeno[4, 3-d]tiazolila, 4, 5-dihidrotiazolo[5, 4-c]quinolila, 8H-indeno[1, 2-d]tiazolila, e 5, 6-dihidro- 4H-3-tia-1-aza-benzo[e]azulenila.
[051] Como "heteroarila" em R2, piridila, furila, tienila, tiazolila, oxazolila, tiadiazolila, oxadiazolila, e triazolila são preferidos. Outros exemplos preferidos incluem piridila, furila, tienila, tiazolila.
[052] Como "heteroarila" em R8, piridila, furila, tienila, tiazolila, oxazolila, tiadiazolila, oxadiazolila, e triazolila são preferidos. Outros exemplos preferidos incluem piridila, furila, tienila, e tiazolila.
[053] Como "heteroarila" em R19, piridila, furila, e tienila são preferidas.
[054] Como "heteroarila" em W1, pirrolila, imidazolila, pirazolila, triazolila, e tetrazolila são preferidas.
[055] Conforme usado neste relatório, "heteroarilalquila" inclui "alquila" em que uma ou duas ou mais de "heteroarila"são substituídos em uma posição arbitrária do mesmo, e estes podem ser substituídos em todas as posições possíveis. Exemplos incluem tienilmetila (por exemplo 2-tienilmetila), tieniletila (por exemplo 2-(tiofen-2-ila)etila), furilmetila (por exemplo 2-furilmetila), furiletila (por exemplo 2-(furan-2- ila)etila), pirrolilmetila (por exemplo 2-pirrolilmetila), pirroliletila (por exemplo 2-(pirrol-2-ila)etila), imidazolilmetila (por exemplo 2- imidazolilmetila, 4-imidazolilmetila), imidazoliletila (por exemplo 2- (imidazol-2-ila)etila), pirazolilmetila (por exemplo 3-pirazolilmetila), pirazoliletila (por exemplo 2-(pirazol-3-ila)etila), tiazolilmetila (por exemplo 2-tiazolilmetila), tiazoliletila (por exemplo 2-(tiazol-2-ila)etila), isotiazolilmetila (por exemplo 3-isotiazolilmetila), isooxazolilmetila (por exemplo 3-isooxazolilmetila), oxazolilmetila (por exemplo 2- oxazolilmetila), oxazoliletila (por exemplo 2-(oxazol-2-ila)etila), piridilmetila (por exemplo 2-piridilmetila, 3-piridilmetila, 4-piridiilmetila), e piridiletila (por exemplo 2-piridiletila).
[056] Conforme usado neste relatório, o termo "acila" que é usado isolado, ou em combinação com outro termo inclui alquilcarbonila em que uma parte alquila é o "alquila", haloalquilcarbonila em que uma parte haloalquila é a "haloalquila", alquenilcarbonila em que uma parte alquenila é o "alquenila", aralquilcarbonila em que uma parte aralquila é o "aralquila", e arilcarbonila em que uma parte arila é o "arila". Exemplos incluem acetila, propionila, butiroila, trifluormetilcarbonila, vinilcarbonila, fenilacetila, e benzoila. A "alquila", o "alquenila" e o "arila" podem ser substituídos com cada substituinte descrito abaixo.
[057] Como "acila" em R10 e R11, acetila, benzoila, e fenilacetila são preferidas.
[058] Como "acila" em R12 e R13, acetila, benzoila, e fenilacetila são preferidas.
[059] Como "acila" em R9, acetila, benzoila, e fenilacetila são preferidas.
[060] Conforme usado neste relatório, exemplos de "acilóxi" incluem acetilóxi, propionilóxi, e benzoilóxi.
[061] Conforme usado neste relatório, um termo "amina opcionalmente substituída"que é usado isolado, ou em combinação com outro termo inclui amina opcionalmente substituída com o "alquila" opcionalmente substituído com um substituinte selecionado do grupo A de substituintes, "haloalquila", "alquenila", "alquinila", "alquilsulfonila", "alquilsulfonilalquila", "alquiloxicarbonila", "aminocarboniloxialquila", "alquilóxi", "alquiloxialquila" opcionalmente substituído com um substituinte selecionado do grupo A de substituintes, "cicloalquila" opcionalmente substituído com um substituinte selecionado do grupo A de substituintes, "arila" opcionalmente substituído com um substituinte selecionado do grupo G de substituintes que consiste em alquila, alquenila, e aralquila, "aralquila", "heteroarila", "heteroarilalquila", "acila", "aminocarbonilalquila" opcionalmente substituído com um substituinte selecionado do grupo G de substituintes, "aminoalquil- carbonila" opcionalmente substituído com um substituinte selecionado do grupo G de substituintes, "alqueniloxicarbonila" em que uma parte alquenilóxi é "alquenilóxi", e "aralquiloxicarbonila" em que uma parte aralquilóxi é "aralquilóxi"em uma ou duas posições. Exemplos incluem amino, metilamino, dimetilamino, etilmetilamino, dietilamino, etilmetila- mino, diisopropilamino, benzilamino, acetilamino, trifluormetilcarbonila, benzoilamino, metiloxicarbonilamino, etiloxicarbonilamino, n- propiloxicarbonilamino, isopropiloxicarbonilamino, n-butilóxi, isobutiloxi- carbonilamino, sec-butiloxicarbonilamino, terc-butiloxicarbonilamino, aliloxicarbonilamino, benziloxicarbonilamino, ciclopentilamino, e ciclohexilamino.
[062] Como um substituinte do "amina opcionalmente substituída"em R3 e R4, alquila, acila, e outros são preferidos.
[063] Como um substituinte do "amina opcionalmente substituída"em R6 e R7, alquila e outros são preferidos.
[064] Como um substituinte da "amina opcionalmente substituída"e do "aminocarbonila opcionalmente substituída"em um grupo de substituintes A, alquila, alquenila, alquinila, arila opcionalmente substituída com um substituinte selecionado do grupo I de substituintes, aralquila, alquilóxi, hidroxialquila, hidroxialquiloxialquila, haloalquila, aminoalquila opcionalmente substituída com 1 ou 2 alquila(s), alquilsulfonila, alquilsulfonilalquila, alquilcarbonila opcionalmente substituído com halogênio ou alquilóxi, alquiloxicarbonila, cicloalquila opcionalmente substituída com um substituinte selecionado do grupo I de substituintes, carboxialquila, aminocarbonilalquila opcionalmente substituída com um substituinte selecionado do grupo G de substituintes, aminocarboniloxialquila opcionalmente substituída com um substituinte selecionado do grupo G de substituintes, alquiloxialquila, alquiltioalquila, alquilcarbonilaminoalquila, alquilsulfo- nilaminoalquila, alquilsulfonila(alquila)aminoalquila, alquiloxicarboni- lalquila, alquiltio(hidroxi)alquila, cicloalquilalquila, cianoalquila, aminoalquilcarbonila opcionalmente substituído com um substituinte selecionado do grupo G de substituintes, heteroarila opcionalmente substituída com um substituinte selecionado do grupo G de substituintes, heteroarilalquila, hidroxialquiloxialquila, um grupo heterocíclico não aromático opcionalmente substituído com um substituinte selecionado do grupo I de substituintes, e um alquila heterocíclico não aromático opcionalmente substituído com um substituinte selecionado do grupo I de substituintes.
[065] Aqui, como um substituinte na "aminocarbonila opcionalmente substituída", alquila, alquenila, aralquila, e outros são preferidos. Particularmente, alquila é preferido.
[066] Como um substituinte na "aminocarbonila opcionalmente substituída"em um grupo B de substituintes, alquila, alquenila, aralquila, e outros são preferidos.
[067] Como um substituinte na "aminocarbonila opcionalmente substituída"em um grupo D de substituintes, alquila, alquenila, aralquila, e outros são preferidos.
[068] Como um substituinte no "aminocarbonila opcionalmente substituída"em um grupo E de substituintes, alquila, alquenila, aralquila, e outros são preferidos.
[069] Como um substituinte no "aminocarbonila opcionalmente substituída"em um grupo H de substituintes, alquila, alquenila, aralquila, e outros são preferidos.
[070] Aqui, como um substituinte no "aminocarbonilalquila opcionalmente substituída", alquila, alquenila aralquila, e outros são preferidos. Particularmente, alquila é preferida.
[071] Como um substituinte no "aminocarbonilalquila opcionalmente substituída"em um grupo C de substituintes, alquilalquenila, aralquila, e outros são preferidos.
[072] Aqui, como um substituinte no "aminocarboniloxialquila opcionalmente substituída", alquila, alquenila, aralquila, e outros são preferidos. Particularmente, alquila é preferido.
[073] Como um substituinte no "aminocarboniloxialquila opcionalmente substituída"em um grupo C de substituintes, alquila, alquenila, aralquila, e outros são preferidos.
[074] Aqui, como um substituinte na "aminoalquilcarbonila opcionalmente substituído", alquila, alquenila, aralquila, e outros são preferidos. Particularmente, alquila é preferido.
[075] Como um substituinte na "aminoalquilcarbonila opcionalmente substituído"em um grupo C de substituintes, alquila, alquenila, aralquila, e outros são preferidos.
[076] Aqui, o termo "ureído opcionalmente substituído"inclui ureído opcionalmente substituído com "alquila", "cicloalquila", "arila", "aralquila", "heteroarila", "heteroarilalquila", "acila", cianoalquila, ou alquiloxialquila em uma ou duas ou mais posições.
[077] Aqui, o termo "guanidino opcionalmente substituído"inclui guanidino opcionalmente substituído com "alquila", "cicloalquila", "arila", "aralquila", "heteroarila", "heteroarilalquila", "acila", ciano, cianoalquila, ou alquiloxialquila em uma ou duas ou mais posições.
[078] Aqui, exemplos de um substituinte em "alquila opcionalmente substituída"incluem amina opcionalmente substituída, um grupo heterocíclico contendo nitrogênio não aromático opcionalmente substituído, carbonila heterocíclico contendo nitrogênio não aromático opcionalmente substituído, alquila, alquilóxi, ciano, alquilsulfonila, cicloalquila, alquenila, heteroarila, heteroarilóxi, hidróxi, mercapto, alquiltio, halogênio, nitro, carbóxi, alquiloxicarbonila, hidroxialquila, haloalquila, haloalquilóxi, alquilcarbonilóxi, carbamoilóxi, aminocarbonila opcionalmente substituída, aminocarbonilalquilóxi, acila, acilóxi, arilóxi, aralquila, aralquilóxi, guanidino opcionalmente substituído, um grupo azo, e ureído opcionalmente substituído. Estes podem ser substituídos com um ou mais substituintes em todas as posições possíveis.
[079] Como um substituinte na "alquila opcionalmente substituída"em R1, R17 e R19, um substituinte selecionado do grupo A de substituintes, alquilóxi, ciano, halogênio, heteroarila, e outros são preferidos. Particularmente, amina opcionalmente substituída com um substituinte selecionado do grupo C de substituintes, e um grupo heterocíclico contendo nitrogênio não aromático opcionalmente substituído com um substituinte selecionado do grupo D de substituintes são preferidos.
[080] Como um substituinte da "alquila opcionalmente substituída"em R2, um substituinte selecionado do grupo A de substituintes, alquilóxi, alquilcarbonila, e halogênio são preferidos. Particularmente, hidróxi, alquilóxi, e halogênio são preferidos.
[081] Como um substituinte da "alquila opcionalmente substituída"em R3 e R4, alquilóxi, alquiloxicarbonila, aminocarbonila, ciano, e outros são preferidos.
[082] Como um substituinte da "alquila opcionalmente substituída"em R6 e R7, alquilóxi, alquiloxicarbonila, aminocarbonila, ciano, hidróxi, e outros são preferidos.
[083] Como um substituinte da "alquila opcionalmente substituída"em R18, hidróxi, alquilóxi, halogênio, ciano, e outros são preferidos.
[084] Como um substituinte da "alquila opcionalmente substituída"em R20, hidróxi, alquilóxi, halogênio, ciano, e outros são preferidos.
[085] Aqui, exemplos de um substituinte em "alquenila opcionalmente substituída"e em "alquinila opcionalmente substituída"incluem amina opcionalmente substituída, um grupo heterocíclico contendo nitrogênio não aromático opcionalmente substituído, cicloalquila, hidróxi, alquilóxi, mercapto, alquiltio, halogênio, nitro, ciano, carbóxi, alquiloxicarbonila, haloalquila, haloalquilóxi, aminocarbonila opcionalmente substituída, acila, acilóxi, arila, arilóxi, aralquila, aralquilóxi, alquilsulfonila, guanidino, um grupo azo, ureído opcionalmente substituído, e outros. Estes podem ser substituídos com um ou mais substituintes em todas as posições possíveis.
[086] Como um substituinte do "alquenila opcionalmente substituída"em R1 e R17, um substituinte selecionado do grupo A de substituintes é preferido. Em particular, amina opcionalmente substituída com um substituinte selecionado do grupo C de substituintes, e um grupo heterocíclico contendo nitrogênio não aromático opcionalmente substituído com um substituinte selecionado do grupo D de substituintes são preferidos.
[087] Como um substituinte do "alquenila opcionalmente substituída"e do "alquinila opcionalmente substituída"em R2, um substituinte selecionado do grupo A de substituintes, cicloalquila, alquilóxi, e halogênio são preferidos. Particularmente, hidróxi, cicloalquila, alquilóxi, e halogênio são preferidos.
[088] Como um substituinte da "alquenila opcionalmente substituída"e do "alquinila opcionalmente substituída"em R3 e R4, alquilóxi, alquiloxicarbonila, aminocarbonila, alquila opcionalmente substituída com ciano e outros, alquilóxi, alquiloxicarbonila, aminocarbonila, alquiloxicarbonila opcionalmente substituído com ciano e outros, e aminocarbonila opcionalmente substituída, e outros são preferidos.
[089] Como um substituinte da "alquenila opcionalmente substituída"e do "alquinila opcionalmente substituída"em R6 e R7, alquilóxi, alquiloxicarbonila, aminocarbonila, alquila opcionalmente substituída com ciano e outros, alquilóxi, alquiloxicarbonila, aminocarbonila, alquiloxicarbonila opcionalmente substituído com ciano e outros, e aminocarbonila opcionalmente substituída, e outros são preferidos.
[090] Como um substituinte da "alquenila opcionalmente substituída"e da "alquinila opcionalmente substituída"em R18, hidróxi, alquilóxi, halogênio, ciano, e outros são preferidos.
[091] Como um substituinte do "alquenila opcionalmente substituída"e do "alquinila opcionalmente substituída"em R20, hidróxi, alquilóxi, halogênio, ciano, e outros são preferidos.
[092] Aqui, exemplos de um substituinte em "cicloalquila opcionalmente substituída"incluem alquiloxicarbonila, aminocarbonila opcionalmente substituída com um substituinte selecionado do grupo G de substituintes, ciano, alquila opcionalmente substituída com um substituinte selecionado do grupo M de substituintes que consiste em ciano, hidróxi, carbóxi, aminocarbonila, alquiloxicarbonila, e alquilóxi, alquilsulfonila, alquilsulfonilalquilcarbonila, cicloalquila, hidróxi, alquilóxi, mercapto, alquiltio, halogênio, nitro, carbóxi, haloalquila, haloalquilóxi, acila, acilóxi, arila, arilóxi (por exemplo fenilóxi), aralquila, aralquilóxi (por exemplo benzilóxi), um grupo heterocíclico contendo nitrogênio não aromático, alquilcarbonilamino, aminocarbonilóxi, amino, oxo, guanidino, um grupo azo, e ureído opcionalmente substituído.
[093] Como um substituinte do "cicloalquila opcionalmente substituída"no grupo C de substituintes, os substituintes exemplificados no grupo I de substituintes são preferidos.
[094] Aqui, exemplos de um substituinte de "alquilóxi opcionalmente substituído", "alquenilóxi opcionalmente substituído", e "alquinilóxi opcionalmente substituído"incluem cicloalquila, alquenila, hidróxi, alquilóxi, mercapto, alquiltio, halogênio, nitro, ciano, carbóxi, alquiloxicarbonila, haloalquila, haloalquilóxi, amina opcionalmente substituída, aminocarbonila opcionalmente substituída, acila, acilóxi, um grupo heterocíclico não aromático opcionalmente substituído, arilóxi, aralquilóxi, alquilsulfonila, guanidino, um grupo azo, e ureído opcionalmente substituído. Estes podem ser substituídos em um ou mais lugares de todas as posições possíveis. Exemplos preferidos incluem halogênio.
[095] Como um substituinte do "alquilóxi opcionalmente substituído"e do "alquenilóxi opcionalmente substituído"em R3 e R4, alquilóxi, amina opcionalmente substituída, um grupo heterocíclico não aromático opcionalmente substituído com um substituinte selecionado do grupo D de substituintes, ciano, e outros são preferidos.
[096] Como um substituinte de "alquilóxi opcionalmente substituído", "alquenilóxi opcionalmente substituído", e "alquinilóxi opcionalmente substituído"em R5, um substituinte selecionado do grupo E de substituintes é preferido.
[097] Como um substituinte de "alquilóxi opcionalmente substituído", "alquenilóxi opcionalmente substituído", e "alquinilóxi opcionalmente substituído"em R6 e R7, alquilóxi, ciano, alquiloxi- carbonila, aminocarbonila opcionalmente substituída, e outros são preferidos.
[098] Aqui, exemplos de um substituinte no "grupo heterocíclico não aromático opcionalmente substituído"incluem alquiloxicarbonila, aminocarbonila opcionalmente substituída com um substituinte selecionado do grupo G de substituintes, ciano, alquila opcionalmente substituída com um substituinte selecionado do grupo M de substituintes que consiste em ciano, hidróxi, carbóxi, aminocarbonila, alquiloxi- carbonila, e alquilóxi, alquilsulfonila, alquilsulfonilalquilcarbonila, cicloalquila, hidróxi, alquilóxi, mercapto, alquiltio, halogênio, nitro, carbóxi, haloalquila, haloalquilóxi, acila, acilóxi, arila, arilóxi (por exemplo fenilóxi), aralquila, aralquilóxi (por exemplo benzilóxi), um grupo heterocíclico contendo nitrogênio não aromático, alquilcarbonilamino, aminocarbonilóxi, amino, oxo, guanidino, um grupo azo, e ureído opcionalmente substituído.
[099] Aqui, exemplos de um substituinte no "grupo heterocíclico contendo nitrogênio não aromático opcionalmente substituído"incluem alquiloxicarbonila, aminocarbonila opcionalmente substituída com um substituinte selecionado do grupo G de substituintes, ciano, alquila opcionalmente substituída com um substituinte selecionado do grupo M de substituintes que consiste em ciano, hidróxi, carbóxi, aminocarbonila, alquiloxicarbonila, e alquilóxi, alquilsulfonila, alquilsulfonilalquilcarbo- nila, cicloalquila, hidróxi, alquilóxi, mercapto, alquiltio, halogênio, nitro, carbóxi, haloalquila, haloalquilóxi, acila, acilóxi, arila, arilóxi (por exemplo fenilóxi), aralquila, aralquilóxi (por exemplo benzilóxi), um grupo heterocíclico contendo nitrogênio não aromático, alquilcarboni- lamino, aminocarbonilóxi, amina opcionalmente substituída, oxo, guanidino, um grupo azo, e ureído opcionalmente substituído.
[0100] Como um substituinte do "grupo heterocíclico contendo nitrogênio não aromático opcionalmente substituído"em R1 e R17, alquila, alquiloxicarbonila, aminocarbonila opcionalmente substituída com um substituinte selecionado do grupo G de substituintes, ciano, oxo, amino, carboxila, hidroxialquila, cianoalquila, alquiloxialquila, alquilsulfonila, alquilcarbonila, alquenilcarbonila, alquilsulfonilalquilcar- bonila, alquilcarbonilamino, alquilsulfonilamino, carboxialquila, alquiloxicarbonilalquila, e outros são preferidos. Particularmente, os substituintes exemplificados no grupo B de substituintes são preferidos.
[0101] Como um substituinte do "grupo heterocíclico contendo nitrogênio não aromático opcionalmente substituído"em W1, alquila, alquiloxicarbonila, aminocarbonila opcionalmente substituída, ciano, hidroxialquila, cianoalquila, alquiloxialquila, alquilsulfonila, alquilcar- bonila, alquenilcarbonila, alquilsulfonilalquilcarbonila, e outros são preferidos. Particularmente, os substituintes exemplificados no grupo J de substituintes são preferidos.
[0102] Como um substituinte do "grupo heterocíclico contendo nitrogênio não aromático opcionalmente substituído"e do "carbonila heterocíclico contendo nitrogênio não aromático opcionalmente substituído"no grupo A de substituintes, um substituinte selecionado do grupo D de substituintes é preferido.
[0103] Aqui, exemplos de um substituinte em "arila opcionalmente substituída", "fenila opcionalmente substituída", "heteroarila opcionalmente substituída", "piridila opcionalmente substituída", "furila opcionalmente substituída", "tienila opcionalmente substituída", "tiazolila opcionalmente substituída", "oxazolila opcionalmente substituída", "grupo heterocíclico não aromático opcionalmente substituído", "alquila heterocíclico não aromático opcionalmente substituído", "cicloalquila opcionalmente substituída", "aralquila opcionalmente substituída", e "heteroarilalquila opcionalmente substituída"incluem alquila opcionalmente substituída (como substituinte, halogênio, hidróxi, nitro, ciano, carbóxi, alquilóxi, alquiloxicarbonila, acila, etc.), cicloalquila, alquenila, alquinila, hidróxi, alquilóxi, aralquilóxi, mercapto, alquiltio, halogênio, nitro, ciano, carbóxi, alquiloxicarbonila, ariloxicarbonila, haloalquila, haloalquilóxi, amina opcionalmente substituída, aminocar-bonila opcionalmente substituída, acila, acilóxi, arila opcionalmente substituída (como substituinte, halogênio, hidróxi, nitro, ciano, carbóxi, alquilóxi, alquiloxicarbonila, acila, etc.), heteroarila opcionalmente substituída (como substituinte, halogênio, hidróxi, nitro, ciano, carbóxi, alquilóxi, alquiloxicarbonila, acila, etc.), um grupo heterocíclico não aromático opcionalmente substituído (como substituinte, halogênio, hidróxi, nitro, ciano, carbóxi, alquilóxi, alquiloxicarbonila, acila, etc.), aralquila opcionalmente substituída (como substituinte, halogênio, hidróxi, nitro, ciano, carbóxi, alquilóxi, alquiloxicarbonila, acila, etc.), alquilsulfonila, guanidino, um grupo azo, -N = N- (fenila opcionalmente substituída), e ureído opcionalmente substituído. Estes podem substituir em uma ou mais de todas as posições possíveis.
[0104] Como um substituinte de "arila opcionalmente substituída"em R1, substituintes exemplificados no grupo I de substituintes são preferidos.
[0105] Como um substituinte de "arila opcionalmente substituída"e "heteroarila opcionalmente substituída"em R2, alquila opcionalmente substituída com hidróxi ou amina opcionalmente substituída, amina opcionalmente substituída, halogênio, e outros são preferidos. Particularmente, alquila opcionalmente substituída com hidróxi ou amina opcionalmente substituída é preferida.
[0106] Como um substituinte do "arila opcionalmente substituída", do "heteroarila opcionalmente substituída", e do "grupo heterocíclico não aromático opcionalmente substituído"em R8, alquiloxicarbonila, aminocarbonila opcionalmente substituída, ciano, halogênio, alquila, alquilóxi, alquiltio, haloalquila e outros são preferidos. Particularmente, substituintes exemplificados no grupo F de substituintes são preferidos.
[0107] Como um substituinte de "arila opcionalmente substituída"e "heteroarila opcionalmente substituída"em R19, alquiloxicarbonila, aminocarbonila opcionalmente substituída, ciano, cianoalquila, hidroxi- alquila, aminocarbonilalquila. e outros são preferidos. Particularmente, substituintes exemplificados no grupo I de substituintes são preferidos.
[0108] Como um substituinte de "heteroarila opcionalmente substituída"em W1, alquila, hidróxi, alquilóxi, e outros são preferidos. Particularmente, substituintes exemplificados no grupo J de substituintes são preferidos.
[0109] Como um substituinte do "arila opcionalmente substituída", do "heteroarila opcionalmente substituída", do "grupo heterocíclico não aromático opcionalmente substituído"e do "alquila heterocíclico não aromático opcionalmente substituído"em um grupo C de substituintes, substituintes exemplificados no grupo I de substituintes são preferidos.
[0110] Aqui, a "composição farmacêutica útila para tratar câncer e a "terapêutica para um câncer"incluem produtos terapêuticos para tumor cerebral (por exemplo glioblastoma), câncer de órgão urinário (por exemplo câncer de bexiga, câncer renal), câncer genital (câncer de próstata, câncer de ovário, câncer de útero), tumor linfóide, câncer do trato digestivo (por exemplo câncer de estômago, câncer de intestino grosso), câncer de faringe, câncer de pulmão (por exemplo câncer de glândulas pulmonares, câncer de pulmão de células pequenas, câncer de pulmão de células não-pequenas), câncer de pâncreas, câncer de mama, câncer de cabeça e pescoço, câncer de esôfago, e glândula tireóide. Em particular, a composição é de preferência usada como produto terapêutico para câncer de mama, tumor cerebral, câncer de bexiga, câncer renal, câncer de próstata, câncer de ovário, câncer de útero, câncer de pulmão, câncer de pâncreas, câncer de intestino grosso, câncer de cabeça de pescoço.
[0111] A presente invenção inclui um método para tratar ou prevenir um câncer em um mamífero no qual é necessário tratar ou prevenir um câncer, e o método compreende administrar uma quantidade terapeuticamente eficaz do composto de fórmula (I) ao mamífero. Um câncer que é de preferência tratado é selecionado de tumor cerebral (por exemplo glioblastoma), câncer de órgão urinário (por exemplo câncer de bexiga, câncer renal), câncer genital (câncer de próstata, câncer de ovário, câncer de útero), tumor linfóide, câncer do trato digestivo (por exemplo câncer de estômago), câncer de faringe, câncer de pulmão (por exemplo câncer de glândulas pulmonares, câncer de pulmão de células pequenas, câncer de pulmão de células não- pequenas), câncer de pâncreas, câncer de mama, câncer de cabeça e pescoço, câncer de esôfago, e glândula tireóide. Mais preferivelmente são câncer de mama, tumor cerebral, câncer de bexiga, câncer renal, câncer de próstata, câncer de ovário, câncer de útero, câncer de pulmão, câncer de pâncreas, câncer de intestino grosso e câncer de cabeça de pescoço.
Efeito da Invenção
[0112] O presente composto possui a ação excelente de inibir um receptor de EGF e HER2, e é bastante seguro (possui atividade inibitória de CYP reduzida) e, portanto, é útila como medicamento, entre outras coisas, como um produto terapêutico para câncer.
Melhor modo de realizar a invenção
[0113] O presente composto (I) pode ser sintetizado por qualquer um dos métodos A a E descritos abaixo. Alternativamente, visto que um método para sintetizar um derivado de quinazolina está descrito no documento WO 96/09294, WO 98/02434 e outros, o presente composto (I) também pode ser sintetizado de acordo com este. Quando o composto tem um grupo que tem influência em cada reação, o grupo pode ser protegido com um grupo protetor adequado, e pode ser desprotegido em um estágio adequado. Além disso, quando uma matéria-prima, um reagente, um intermediário e um produto reacional em cada etapa pode formar um sal, o sal está incluído. (Método A) Fórmula química 25
Figure img0025
onde Hal1 e Hal2 são cada independentemente halogênio; R1, R5, R6, e R7 são como definidos no item (1).
Etapa 1
[0114] A primeira etapa é a etapa de sintetizar um composto (iii) por reação de uma matéria-prima de partida (S.M.) que pode ser sintetizada de acordo com o método descrito no documento WO 96/09294 ou outros, ou que está comercialmente disponível, e um composto (ii) que pode ser sintetizado de acordo com o método descrito no documento WO 98/02434 ou outros, ou que está comercialmente disponível.
[0115] A matéria-prima de partida (S.M.) e o composto (ii) podem ser reagidos em um solvente tal como tetrahidrofurano, acetonitrila e outros a uma temperatura de 20°C até uma temperatura abaixo do refluxo térmico, de preferência a uma temperatura de 60°C até uma temperatura abaixo do refluxo térmico, para obter o composto (iii).
Etapa 2
[0116] A segunda etapa é a etapa de inserir monóxido de carbono no composto (iii) na presença de um catalisador à base de paládio para obter um composto (iv).
[0117] O composto (iii) pode ser reagido a uma temperatura de 50°C a 150°C, de preferência 70°C a 90°C sob a atmosfera de monóxido de carbono em um solvente tal como N,N- dimetilformamida, N,N-dimetilacetamida, N,N'-dimetilimidazolidinona, dimetila sulfóxido e outros, na presença de uma fonte de hidrogênio tal como formiato de sódio, hidreto de tributila estanho e outros, um catalisador à base de paládio tal como diclorobis(trifenilfosfina)paládio, tetracis(trifenilfosfina)paládio, tris(dibenzilidenoacetona)dipaládio, [1, 1'- bis(difenilfosfino)ferroceno]dicloropaládio, acetato de paládio + trifenilfosfina e outros, e uma base tal como trietilamina, di(isopropila)etilamina e outros para obter o composto (iv).
Etapa 3
[0118] A terceira etapa é uma etapa de sintetizar um composto desejado (v) por reação do composto (iv) e um composto representado pela fórmula: R1-O-NH2 onde R1é como definido no item (1).
[0119] A matéria-prima de partida (iv) e o composto representado pela fórmula: R1-O-NH2 onde R1é como definido no item (1) ou um sal podem ser reagidos a uma temperatura de 0°C até uma temperatura abaixo do refluxo térmico, de preferência, a uma temperatura de 20°C a 70°C, em um solvente tal como tetrahidrofurano, dioxano, metanol e outros, ou em um solvente misto dos mesmos e água, se necessário, na presença de um ácido tal como ácido clorídrico, ácido sulfúrico, ácido p-toluenossulfônico, ácido metanossulfônico, ácido fórmico, ácido acético, ácido trifluoracético e outros para obter o composto (v). (Método B) Fórmula química 26
Figure img0026
onde R1, R5, R6, e R7 são como definidos no item (1).
(Etapa 1)
[0120] A primeira etapa é a etapa de sintetizar um composto desejado (v) por reação de um composto (v') obtido pela reação do composto (iv) obtido no método A com hidroxilamina, e um composto representado pela fórmula: R1-Hal3 onde Hal3 é halogênio; R1 é como definido no item (1).
[0121] O composto (v') e o composto representado pela fórmula: R1- Hal3 onde Hal3 é halogênio; R1 é como definido no item (1) podem ser dissolvidos em um solvente tal como N,N-dimetilacetamida, N,N- dimetilacetamida, N,N'-dimetilimidazolidinona, dimetila sulfóxido e outros, e reagidos a uma temperatura de 50°C a 150°C, de preferência 60oC a 80°C na presença de uma base tal como carbonato de potássio, carbonato de sódio, e outras para obter o composto (v). (Método C) Fórmula química 27
Figure img0027
onde R1, R5, R6, e R7 são como definidos no item (1).
(Etapa 1)
[0122] A primeira etapa é uma etapa de sintetizar um composto desejado (xv) por reação de um composto (v') obtido por reação do composto (iv) obtido no Método A com hidroxilamina, e um composto representado pela fórmula: R1-CH=CH2 onde R1 é como definido no item (1).
[0123] O composto (xv) pode ser obtido por dissolução do composto (v') em um solvente tal como clorofórmio, diclorometano, 1, 2-dicloroetano e outros, e reação com um agente oxidante à base de cloro tal como N- clorosuccinimida, N-cloroftalimida e outros a uma temperatura de 20°C a 100°C, de preferência 50°C a 60°C na presença de uma quantidade catalítica de uma base tal como piridina, 4-dimetilaminopiridina e outros, e subseqüentemente, adição de um composto representado pela fórmula: R1-CH=CH2 onde R1 é como definido no item (1), e uma base tal como trietilamina, di(isopropila)etilamina e outros, e reação dos mesmos a uma temperatura de 0°C a 100°C, de preferência 10°C a 30°C. (Método D) Fórmula química 28
Figure img0028
Figure img0029
onde R1, R2, R5, R6, e R7 são como definidos no item (1)
(Etapa 1)
[0124] A primeira etapa é a etapa de reagir o composto (iv) obtido no método A com um reagente representado pela fórmula: R2MgHal4 ou R2Li onde Hal4 é halogênio; R2 é como definido no item (1) para obter um composto (vi).
[0125] O composto (vi) pode ser obtido por reação do composto (iv) e do reagente representado pela fórmula: R2MgHal4 ou R2Li onde Hal4 é halogênio; R2 é como definido no item (1) a uma temperatura de -100°C a 50°C, de preferência, -78°C a 10°C em um solvente tal como tetrahidrofurano, éter dietílico, tolueno, n-hexano e outros.
(Etapa 2)
[0126] A segunda etapa é a etapa de oxidar o composto (vi) para sintetizar um composto (vii).
[0127] O composto (vii) pode ser obtido por oxidação do composto (vi) por um método geral de oxidação de um álcool secundário descrito em Experimental Chemistry Course, vol. 23, Fourth edition (editado por The Chemical Society of Japan) ou outros. (Etapa 3)
[0128] De acordo com o mesmo método da terceira etapa do Método A, é possível obter um composto (viii) a partir do composto (vii). (Método E) Fórmula química 29
Figure img0030
onde Hal8 é halogênio; R43 é um grupo representado pela fórmula: R44(R45O)N onde R44 e R45 são independentemente C1-C3 alquila ou um grupo representado pela fórmula: Fórmula química 30
Figure img0031
onde W2 é um grupo heterocíclico contendo nitrogênio não aromático; R46 é C1-C3 alquila ou um grupo representado pela fórmula: Fórmula química 31
Figure img0032
onde L1 é C2-C3 alquileno; R1, R2, R5, R6, e R7 são como definidos no item (1)
(Etapa 1)
[0129] A primeira etapa é a etapa de obter um composto (x) por reação do composto (iii) obtido no A método com um álcool ou um reagente representado pela fórmula: Fórmula química 32
Figure img0033
onde L1 é C2-C3 alquileno enquanto monóxido de carbono é inserido na presença de um catalisador à base de paládio.
[0130] O composto (x) pode ser obtido por reação do composto (iii) com um álcool tal como metanol, etanol, n-propanol, isopropanol e outros, ou um reagente tal como imida de ácido N-hidroxissuccínico e outros a uma temperatura de 50°C a 150°C, de preferência, 70°C a 90°C sob uma atmosfera de monóxido de carbono em um solvente tal como N,N-dimetilformamida, N,N-dimetilacetamida, N,N'-dimetilimidazo- lidinona, dimetila sulfóxido e outros na presença de um catalisador à base de paládio tal como diclorobis(trifenilfosfina)paládio, tetracis(trifenilfosfina)paládio, tris(dibenzilidenoacetona)dipaládio, [1, 1'- bis(difenilfosfino)ferroceno]dicloropaládio, acetato de paládio + trifenilfosfina, acetato de paládio + 1,3-bisdifenilfosfinopropano e outros, e uma base tal como trietilamina, di(isopropila)etilamina e outras.
(Etapa 2)
[0131] A segunda etapa é uma etapa de obter um composto (xi) por reação do composto (x) com um reagente representado pela fórmula: R44(R45O)NH onde R44 e R45 são independentemente C1-C3 alquila ou um reagente representado pela fórmula: Fórmula química 33
Figure img0034
onde W2é um grupo heterocíclico contendo nitrogênio não aromático.
[0132] O composto (xi) pode ser obtido por misturação do composto (x) com um reagente representado pela fórmula: R44(R45O)NH onde R44 e R45são independentemente C1-C3 alquila ou um reagente representado pela fórmula: Fórmula química 34
Figure img0035
onde W2é um grupo heterocíclico contendo nitrogênio não aromático em um solvente tal como tetrahidrofurano, N,N-dimetilformamida, clorofórmio, diclorometano e outros, e adição de um reagente tal como cloreto de metilmagnésio, brometo de metilmagnésio, cloreto de isopropilmagnésio, metila lítio e outros a uma temperatura de - 100°C a 50°C, de preferência -78°C a 20°C para reagir os mesmos. (Etapa 3)
[0133] A terceira etapa é uma etapa de reagir o composto (xi) com um reagente representado pela fórmula: R2M onde M é Li, Na, K, ou um grupo representado pela fórmula: MgHal5 onde Hal5 é halogênio; R2 é como definido no item (1) para obter um composto (vii).
[0134] O composto (vii) pode ser obtido por reação do composto (xi) com um reagente representado pela fórmula: R2M onde M é Li, Na, K, ou um grupo representado pela fórmula: MgHal5 onde Hal5 é halogênio; R2 é como definido no item (1) a uma temperatura de - 100°C a 50°C, de preferência -78°C a 20°C em um solvente tal como tetrahidrofurano, éter dietílico, tolueno, n-hexano e outros.
(Etapa 4)
[0135] Da mesma maneira que para a terceira etapa do Método A, um composto (viii) pode ser obtido a partir do composto (vii).
[0136] Como um método alternativo para a primeira etapa e a segunda etapa do Método E, temos o Método E' a seguir. Fórmula química 35
Figure img0036
onde Hal8 e R43 são como definidos acima; R5, R6, e R7 são como definidos no item (1).
(Etapa 1)
[0137] A primeira etapa é uma etapa de obter um composto (xi) por reação do composto (iii) com um reagente representado pela fórmula: R43H onde R43 é como definido acima enquanto monóxido de carbono é inserido na presença de um catalisador à base de paládio.
[0138] Por reação de um reagente representado por R43H onde R43 é como definido acima no lugar de álcool ou outros da mesma maneira que aquela da primeira etapa do Método E, o composto (xi) pode ser obtido a partir do composto (iii).
[0139] Como outro método para obter um derivado tipo amida (xi) do método E, temos o método E" a seguir. (Método E") onde Hal6é halogênio; Hal7é halogênio; R43 e R46são como definidos acima; R5, R6, e R7são como definidos no item (1). Fórmula química 36
Figure img0037
(Etapa 1)
[0140] Da mesma maneira que para a primeira etapa do Método E, um composto (xii) pode ser obtido a partir de um composto (xvi).
(Etapa 2)
[0141] Da mesma maneira que para a segunda etapa do Método E, um composto (xiii) pode ser obtido a partir do composto (xii).
(Etapa 3)
[0142] A terceira etapa é uma etapa de converter um grupo hidroxila do composto (xiii) em halogênio para obter um composto (xiv).
[0143] O composto (xiv) pode ser obtido por reação do composto (xiii) com um agente halogenante tal como oxicloreto de fósforo, oxibrometo de fósforo e outros a uma temperatura de 0°C a 200°C, de preferência 20°C a 150°C em um solvente tal como tolueno, tetrahidrofurano e outros na presença de uma base tal como trietilamina, diisopropiletilamina, piridina e outros.
(Etapa 4)
[0144] Da mesma maneira que para a primeira etapa do Método A, um composto (xi) pode ser obtido a partir do composto (xiv).
[0145] O presente composto (I) no qual A é um grupo representado pela fórmula: Fórmula química 37
Figure img0038
onde Y2 é uma ligação simples ou C1-C3 alquileno; R6, R7, e R8 são como definidos no item (1) também pode ser sintetizado pelo Método F a seguir. (Método F) Fórmula química 38
Figure img0039
onde Hal6 e Hal7 são halogênio; Y2 é uma ligação simples ou C1-C3 alquileno; Pg é um grupo protetor adequado para um grupo hidroxila; R1, R2, R6, R7, e R8 são como definidos no item (1); R43 e R46 são como definidos acima.
(Etapa 1)
[0146] Da mesma maneira que para a primeira etapa do Método A, um composto (iii') pode ser obtido a partir de um composto de partida (S.M.) e um composto (ii').
(Etapa 2)
[0147] A segunda etapa é uma etapa de ligar um grupo protetor a um grupo hidroxila do composto (iii') para sintetizar um composto (iii").
[0148] Um grupo protetor adequado pode ser ligado pelo método descrito em Protective Groups in Organic Synthesis, Theodora W Green (John Wiley & Sons) ou outros.
(Etapa 3)
[0149] Da mesma maneira que para a primeira etapa do Método E, um composto (x') pode ser obtido a partir do composto (iii").
(Etapa 4)
[0150] Da mesma maneira que para a segunda etapa do Método E, um composto (xi') pode ser obtido a partir do composto (x').
(Etapa 5)
[0151] Da mesma maneira que para a terceira etapa do Método E, um composto (vii') pode ser obtido a partir do composto (xi').
(Etapa 6)
[0152] Da mesma maneira que para a terceira etapa do Método A, um composto (viii') pode ser obtido a partir do composto (vii').
(Etapa 7)
[0153] A sétima etapa é uma etapa de remover um grupo protetor do composto (viii') para sintetizar um composto (viii").
[0154] A desproteção pode ser efetuada na condição adequada pelo método descrito em Protective Groups in Organic Synthesis, Theodora W Green (John Wiley & Sons) ou outros.
(Etapa 8)
[0155] A oitava etapa é uma etapa de reagir o composto (viii") com um reagente representado pela fórmula: R8-Y2-Hal8 onde Hal8 é halogênio; Y2 é uma ligação simples ou C1-C3 alquileno; R8 é como definido no item (1) para obter um composto (viii"').
[0156] O composto (viii"') pode ser obtido por reação do composto (viii") com um reagente representado pela fórmula: R8-Y2-Hal8 onde Hal8 é halogênio; Y2 é uma ligação simples ou C1-C3 alquileno; R8 é como definido no item (1) a uma temperatura de -20°C a 200°C, de preferência 0°C a 100°C em um solvente tal como N,N-dimetilformamida, dimetila sulfóxido, tetrahidrofurano, éter dietílico, tolueno, n-hexano e outros na presença de uma base tal como carbonato de césio, carbonato de potássio, carbonato de sódio, carbonato de lítio, bicarbonato de potássio, bicarbonato de sódio, hidróxido de potássio, hidróxido de sódio, trietilamina, piridina e outros.
[0157] Como Y2 no Método F, C1-C3 alquileno é preferido. Particularmente, metileno é preferido.
[0158] Como R8 no Método F, fenila opcionalmente substituída com halogênio, ou piridila opcionalmente substituída com halogênio é preferido.
[0159] Um reagente tipo alcoxiamino representado pela fórmula: R1- O-NH2 onde R1é como definido no item (1) usado na terceira etapa do Método A encontra-se comercialmente disponível, ou pode ser sintetizado usando, como matéria-prima de partida, um composto tipo álcool que pode ser sintetizado de acordo com o método descrito em J. Med. Chem., 1999, 42:2007-2020, Liebigs Ann. Chem., 1988:11491153, Organic Letters, 2004, 6:4069-4072, Organic Letters, 2005, 7:937939, WO 04/054514 ou outros, de acordo com o método descrito no documento WO 02/062313 ou outros.
[0160] No composto representado pela fórmula (I), os compostos representados pela fórmula (I-A) até a fórmula (I-P) a seguir são preferidos.
[0161] Um composto representado na fórmula (I-A): Fórmula química 39
Figure img0040
onde R21é alquila substituída com amina opcionalmente substituída com um substituinte selecionado do grupo C de substituintes que consiste em alquila, alquenila, alquinila, arila opcionalmente substituída, aralquila, alquilóxi, hidroxialquila, hidroxialquiloxialquila, haloalquila, aminoalquila opcionalmente substituída com 1 ou 2 alquila(s), alquilsulfonila, alquilsulfonilalquila, alquilcarbonila opcionalmente substituído com halogênio ou alquilóxi, alquiloxicarbonila, cicloalquila opcionalmente substituída, carboxialquila, aminocarbonilalquila opcionalmente substituída, aminocarboniloxialquila opcionalmente substituída, alquiloxialquila, alquiltioalquila, alquilcarbonilaminoalquila, alquilsulfonilaminoalquila, alquilsulfonila(alquila)aminoalquila, alquiloxi- carbonilalquila, alquiltio(hidroxi)alquila, cicloalquilalquila, cianoalquila, aminoalquilcarbonila opcionalmente substituído, heteroarila opcional-mentesubstituída, heteroarilalquila, hidroxialquiloxialquila, um grupo heterocíclico não aromático opcionalmente substituído, e alquila heterocíclico não aromático opcionalmente substituído; alquila substituída com um grupo heterocíclico contendo nitrogênio não aromático, onde o grupo heterocíclico contendo nitrogênio não aromático é selecionado de pirrolidinila, piperidila, piperazinila, morfolinila, e tiomorfolinila, opcionalmente substituído com um substituinte selecionado do grupo D de substituintes que consiste em halogênio; arila; hidróxi; oxo; aminocarbonila opcionalmente substituída; alquiloxicarbonila; alquila opcionalmente substituída com um substituinte selecionado do grupo H de substituintes que consiste em aminocarbonila opcionalmente substituída, ciano, alquilóxi, alquilsulfonilamino, amino, carbóxi, alquiloxicarbonila, e hidróxi; alquilaminocarbonila; carbóxi; ciano, alquilsulfonila; alquilcarbonila; alquenilcarbonila; alquilsulfonilalquilcarbonila; alquiloxialquilcarbonila; alquilcarbonilamino; aminocarbonilóxi; um grupo heterocíclico contendo nitrogênio não aromático; e carbonila heterocíclico não aromático; ou um grupo heterocíclico contendo nitrogênio não aromático, onde o grupo heterocíclico contendo nitrogênio não aromático é selecionado de azetidinila, pirrolidinila, e piperidila, opcionalmente substituído com um substituinte selecionado do grupo B de substituintes que consiste em alquiloxicarbonila, aminocarbonila opcionalmente substituída, oxo, amino, carbóxi, ciano, cianoalquila, hidroxialquila, alquilcarbonilamino, alquilsulfonilamino, e aminocarbonilalquila; R22é alquila opcionalmente substituída com um substituinte selecionado do grupo K de substituintes que consiste em amina opcionalmente substituída com alquila, hidróxi, alquilóxi, e halogênio; alquenila opcionalmente substituída com um substituinte selecionado do grupo K de substituintes, alquinila opcionalmente substituída com um substituinte selecionado do grupo K de substituintes; hidróxi; halogênio; fenila; piridila; furila; tienila; ou tiazolila; um de R23 e R24é um átomo de hidrogênio, e o outro é um átomo de hidrogênio, alquilóxi, alquiloxialquilóxi, halogênio, ou aminoalquila opcionalmente substituída com alquila; R27é um átomo de hidrogênio, alquila, ou acila; e R25 e R26são cada um independentemente um átomo de hidrogênio, halogênio, alquinila, hidróxi, alquilóxi, alquenilóxi, alquinilóxi, ou heteroarilalquilóxi, seu sal farmaceuticamente aceitável, ou um solvato do mesmo.
[0162] Um composto representado pela fórmula (I-B): Fórmula química 40
Figure img0041
onde R21, R22, R23, R24 e R27são como definidos acima; Y1é C1-C3 alquileno; R28é alquila, alquilóxi, alquinila, ou halogênio; e R29, R30, e R31são cada um independentemente um átomo de hidrogênio ou um substituinte selecionado do grupo F de substituintes que consiste em halogênio, carbóxi, alquila, haloalquila, hidroxialquila, alquilóxi, alquiloxicarbonila, e amina opcionalmente substituída, seu sal farmaceuticamente aceitável, ou um solvato do mesmo.
[0163] Um composto representado pela fórmula (I-C): Fórmula química 41
Figure img0042
onde R21, R22, R23, R24, e R27são como definidos acima; R35é alquila opcionalmente substituída com um substituinte selecionado do grupo L de substituintes que consiste em hidróxi, alquilóxi, halogênio, e ciano; alquenila opcionalmente substituída com um substituinte selecionado do grupo L de substituintes; alquinila opcionalmente substituída com um substituinte selecionado do grupo L de substituintes; ou um grupo representado pela fórmula: Fórmula química 42
Figure img0043
onde R29, R30, e R31são como definidos acima; Q é N ou CH2, seu sal farmaceuticamente aceitável, ou um solvato do mesmo.
[0164] Um composto representado pela fórmula (I-D): Fórmula química 43
Figure img0044
onde R21, R22, R23, R24, R25, R26, e R27são como definidos acima; e R36 é alquila substituída com aminocarbonila opcionalmente substituída com um substituinte selecionado do grupo C de substituintes ou alquila substituída com carbonila heterocíclico não aromático, onde o heterociclo contendo nitrogênio não aromático é selecionado de pirrolidinila, piperidinila, piperazinila, morfolinila, e tiomorfolinila, opcionalmente substituído com um substituinte selecionado do grupo D de substituintes, seu sal farmaceuticamente aceitável, ou um solvato do mesmo.
[0165] Um composto representado pela fórmula (I-E): Fórmula química 44
Figure img0045
onde R21, R22, R23, R24, R27, R28, R29, R30, R31, R36, e Y1são como definidos acima, seu sal farmaceuticamente aceitável, ou um solvato do mesmo.
[0166] Um composto representado pela fórmula (I-F): Fórmula química 45
Figure img0046
onde R22, R23, R24, R27, R36, e Q são como definidos acima, seu sal farmaceuticamente aceitável, ou um solvato do mesmo.
[0167] Um composto representado pela fórmula (I-G): Fórmula química 46
Figure img0047
onde R23, R24, R25, R26, e R27são como definidos acima; R32é alquila substituída com amina opcionalmente substituída com um substituinte selecionado do grupo C de substituintes, alquila substituída com um grupo heterocíclico contendo nitrogênio não aromático, onde o grupo heterocíclico contendo nitrogênio não aromático é selecionado de pirrolidinila, piperidila, piperazinila, morfolinila, e tiomorfolinila, opcionalmente substituído com um substituinte selecionado do grupo D de substituintes, ou um grupo heterocíclico contendo nitrogênio não aromático, onde o grupo heterocíclico contendo nitrogênio não aromático é selecionado de azetidinila, pirrodilinila, e piperidila, opcionalmente substituído com um substituinte selecionado do grupo B de substituintes, seu sal farmaceuticamente aceitável, ou um solvato do mesmo.
[0168] Um composto representado pela fórmula (I-H): Fórmula química 47
Figure img0048
onde R23, R24, R27, R28, R29, R30, R31, R32, e Y1são como definidos acima, seu sal farmaceuticamente aceitável, ou um solvato do mesmo.
[0169] Um composto representado pela fórmula (I-I): Fórmula química 48
Figure img0049
onde R23, R24, R27, R32, R35, e Q são como definidos acima, seu sal farmaceuticamente aceitável, ou um solvato do mesmo.
[0170] Um composto representado pela fórmula (I-J): Fórmula química 49
Figure img0050
onde R22, R23, R24, R25, R26, e R27são como definidos acima; W2é pirrolidinila opcionalmente substituído com um substituinte selecionado do grupo J de substituintes, piperidila opcionalmente substituído com um substituinte selecionado do grupo J de substituintes, piperazinila opcionalmente substituído com um substituinte selecionado do grupo J de substituintes, morfolinila opcionalmente substituído com um substituinte selecionado do grupo J de substituintes, ou triazolila opcionalmente substituído com um substituinte selecionado do grupo J de substituintes, seu sal farmaceuticamente aceitável, ou um solvato do mesmo.
[0171] Um composto representado pela fórmula (I-K): Fórmula química 50
Figure img0051
onde R22, R23, R24, R27, R28, R29, R30, R31, Y1, e W2são como definidos acima, seu sal farmaceuticamente aceitável, ou um solvato do mesmo.
[0172] Um composto representado pela fórmula (I-L): Fórmula química 51
Figure img0052
:22, :23, :24, :27, :35, W2, e Q são como definidos acima, seu sal farmaceuticamente aceitável, ou um solvato do mesmo.
[0173] Um composto representado pela fórmula (I-M): Fórmula química 52
Figure img0053
onde R22, R23, R24, R25, R26, e R27são como definidos acima; R33é um átomo de hidrogênio, C1-C6 alquila opcionalmente substituída com um substituinte selecionado do grupo L de substituintes, C2-C6 alquenila opcionalmente substituída com um substituinte selecionado do grupo L de substituintes, ou C2-C6 alquinila opcionalmente substituída com um substituinte selecionado do grupo L de substituintes; e R34é alquila substituída com amina opcionalmente substituída com um substituinte selecionado do grupo C de substituintes, alquila substituída com um grupo heterocíclico contendo nitrogênio não aromático opcionalmente substituído com um substituinte selecionado do grupo D de substituintes, arila opcionalmente substituída com um substituinte selecionado do grupo F de substituintes, heteroarila opcionalmente substituída com um substituinte selecionado do grupo F de substituintes, ou um grupo heterocíclico não aromático opcionalmente substituído com um substituinte selecionado do grupo F de substituintes, seu sal farmaceuticamente aceitável, ou um solvato do mesmo.
[0174] Um composto representado pela fórmula (I-N): Fórmula química 53
Figure img0054
onde R22, R23, R24, R27, R28, R29, R30, R31, R33, R34, e Y1são como definidos acima, seu sal farmaceuticamente aceitável, ou um solvato do mesmo.
[0175] Um composto representado pela fórmula (I-O): onde R22, R23, R24, R27, R34, R35, e Q são como definidos acima, seu sal farmaceuticamente aceitável, ou um solvato do mesmo. Fórmula química 54
Figure img0055
[0176] Um composto representado pela fórmula (I-P): Fórmula química 55
Figure img0056
onde R37é alquila substituída com amina opcionalmente substituída com alquila, hidroxialquila, alquilcarbonilaminoalquila ou um grupo heterocíclico não aromático; alquila substituída com um grupo heterocíclico contendo nitrogênio não aromático opcionalmente substituído com alquila, hidroxialquila, ou alquilcarbonilamino; ou um grupo heterocíclico contendo nitrogênio não aromático substituído com hidroxialquila; R38é C2-C4 alquinila; R39é halogênio; R40é um grupo representado pela fórmula: -Y3-R42 onde Y3 é alquileno que pode ser interposto com -O-; R42é fenila opcionalmente substituída com halogênio, ou piridila opcionalmente substituída com halogênio; R41é halogênio; Y1é como definido acima, seu sal farmaceuticamente aceitável, ou um solvato do mesmo.
[0177] Um composto representado pela fórmula (I-Q): Fórmula química 56
Figure img0057
onde R47é um grupo representado pela fórmula: Fórmula química 57
Figure img0058
R37é como definido acima, seu sal farmaceuticamente aceitável, ou um solvato do mesmo.
[0178] Como R22 nos compostos representados pela fórmula (I-A) até a fórmula (I-F) e na fórmula (I-J) até a fórmula (I-O), metila, etila, n- propila, isopropila, propinila, butinila, ou fenila é preferido.
[0179] Aqui, o "solvato" inclui, por exemplo, um solvato com um solvente orgânico, um hidrato e outros. Quando se forma um solvato, o composto pode ser coordenado com um número arbitrário de moléculas de água.
[0180] Quando indicado o "presente composto", um sal farmaceuticamente aceitável, e um hidrato do mesmo também estão incluídos. Exemplos incluem sais de metais alcalinos (lítio, sódio, potássio etc.), ou metais alcalinos-terrosos (magnésio, cálcio etc.), e amônio, bases orgânicas e aminoácido, e sais com ácidos inorgânicos (ácido clorídrico, ácido bromídrico, ácido fosfórico, ácido sulfúrico etc.), ou ácidos orgânicos (ácido acético, ácido cítrico, ácido maléico, ácido fumárico, ácido benzenossulfônico, ácido p-toluenossulfônico etc.). Estes sais podem ser formados por métodos que são normalmente efetuados.
[0181] Além disso, o presente composto não está limitado a isômeros específicos, mas inclui todos os isômeros e racematos possíveis.
[0182] O presente composto, como descrito na seção Exemplos Experimentais descrita adiante, apresenta a excelente atividade inibitória da proliferação celular, e pode ser usado como uma composição farmacêutica útila para tratar câncer"e como um "produto terapêutico para um câncer".
[0183] Quando o presente composto é administrado a um ser humano com o propósito de tratar as doenças acima mencionadas, ele pode ser administrado por via oral como pós, grânulos, comprimidos, cápsulas, pílulas, soluções ou outros, ou podem ser administrados por via parenteral como injetáveis, supositórios, agentes absorventes transdérmicos, inalantes ou outros. E, uma quantidade eficaz do presente composto é misturada, se necessário, com aditivos farmacêuticos tais como excipientes, aglutinantes, agentes umectantes, agentes desintegradores, lubrificantes e outros que são adequados para uma forma de dosagem, dessa forma, o presente composto pode ser formulado como preparações farmacêuticas. No caso de injetáveis, o presente composto junto com um veículo adequado é submetido a um tratamento de esterilização para obter preparações.
[0184] Uma dose é diferente dependendo da condição de uma doença, da via de administração, e da idade ou peso de um paciente, e geralmente varia de 0,1 a 100 mg/kg/dia, de preferência, 1 a 20 mg/kg/dia quando administrada por via oral a um adulto.
[0185] Os exemplos e exemplos de teste a seguir ilustram a presente invenção mais detalhadamente abaixo, mas a presente invenção não está limitada aos mesmos.
[0186] Nos exemplos, são usadas as seguintes abreviações. Me: metila Et: etila nPr: n-propila iPr: isopropila Ph: fenila Exemplos Exemplo 1 Fórmula química 58
Figure img0059
(Etapa 1) Síntese de cloridrato de 4-(3-cloro-4-(3- fluorbenziloxi)fenilamino)-6-iodoquinazolina (III-1)
[0187] Em 180 ml de tetrahidrofurano foram dissolvidos 4-cloro-6- iodoquinazolina (6,0 g) e 3-cloro-4-(3-fluorbenziloxi)anilina (II-1, 5,2 g), seguido de refluxo térmico por 3 horas. Um precipitado foi filtrado, e lavado com tetrahidrofurano para obter cloridrato de 4-(4-(3- fluorbenziloxi)fenilamino)-6-iodoquinazolina (III-1, 10,5 g) como um sólido amarelo. 1H RMN (d6-DMSO δ): 11,47 (1H, brs), 9,25 (1H, s), 8,94 (1H, s), 8,36 (1H, dd, J= 1,8 Hz, J= 8,7 Hz), 7,92 (1H, d, J= 2,7 Hz), 7,71 (1H, d, J= 8,7 Hz), 7,66 (1H, dd, J= 2,7 Hz, J= 8,7 Hz), 7,48 (1H, dt, J= 6,0 Hz, J= 7,8 Hz), 7,37-7,30 (3H, m), 7,19 (1H, dt, J= 2,7 Hz, J= 8,7 Hz), 5,30 (2H, s).
[0188] O composto a seguir foi sintetizado de acordo com o mesmo método usado para a primeira etapa acima. Fórmula química 59
Figure img0060
Tabela 1
Figure img0061
Figure img0062
(Etapa 2) Síntese de 4-(3-cloro-4-(3-fluorbenziloxi)fenilamino)-6- formilquinazolina (IV-1)
[0189] Em 100 ml de dimetilformamida foi dissolvido cloridrato de 4-(4-(3-fluorbenziloxi)fenilamino)-6-iodoquinazolina (III-1, 5,0 g), e 1,25 g de formiato de sódio, diclorobis(trifenilfosfina)paládio (324 mg), e trietilamina (3,2 ml) foram adicionados. A mistura reacional foi desgaseificada, e agitada sob aquecimento a 80°C por 3 horas em uma atmosfera de monóxido de carbono. Em seguida, a mistura reacional foi despejada em água gelada, e extraída com acetato de etila. O extrato foi lavado com água e solução de cloreto de sódio, e secado com sulfato de magnésio. A solução secada foi filtrada por Celite, concentrada, e pulverizada com acetato de etila-hexano (1:2) para obter 4-(4-(3-fluorbenziloxi)fenilamino)-6-formilquinazolina (IV-1, 2,86 g) como um sólido amarelo. 1H RMN (d6-DMSO δ): 10,24 (1H, s), 10,13 (1H, s), 9,16 (1H, s), 8,6 9(1H, s), 8,27 (1H, br d, J= 8,7 Hz), 8,03 (1H, d, J= 2,1 Hz), 7,90 (1H, d, J= 9,0 Hz), 7,74 (1H, dd, J= 2,7 Hz, J= 8,7 Hz), 7,48 (1H, dt, J= 6,0 Hz, J= 8,4 Hz), 7,36-7,30 (2H, m), 7,30 (1H, d, J= 8,7 Hz), 7,19 (1H, br t, J= 8,7 Hz), 5,27 (2H, s).
[0190] O composto a seguir foi sintetizado de acordo com o mesmo método usado para a segunda etapa acima. Fórmula química 60
Figure img0063
Tabela 2
Figure img0064
(Etapa 3) Síntese de 4-(3-cloro-4-(3-fluorbenziloxi)fenilamino)-6-(2-(1- piperidila)etoxiimino)quinazolina (V-1)
[0191] Em uma mistura de tetrahidrofurano (2 ml) e água (0,1 ml) foram dissolvidos 4-(3-cloro-4-(3-fluorbenziloxi)fenilamino)-6- formilquinazolina (IV-1, 50 mg) e dicloridrato de 2-(1- piperidila)etoxiamina (36,5 mg), e a mistura foi agitada à temperatura ambiente por uma noite. A mistura reacional foi diluída com acetato de etila, lavada seqüencialmente com solução aquosa saturada de bicarbonato de sódio, e solução aquosa de cloreto de sódio, e secada em sulfato de magnésio. Depois de concentração, o resíduo foi purificado por cromatografia (eluindo com hexano: acetato de etila = 2:3) sando uma coluna de amino, e ainda novamente purificado por cromatografia em camada fina para obter 4-(3-cloro-4-(3- fluorbenziloxi)fenilamino)-6-(2-(1-piperidila)etoxiimino)quinazolina (V-1, 13 mg). 1H RMN (d6-DMSO, δ): 9,95 (1H, s), 8,63 (1H, s), 8,59 (1H, s), 8,34 (1H, s), 8,10 (1H, d, J= 9,3 Hz), 8,00 (1H, d, J= 2,4 Hz), 7,79 (1H, d, J= 8,7Hz), 7,72 (1H, dd, J= 9,0 Hz, J= 2,1 Hz), 7,51-7,44 (1H, m), 7,36-7,31 (2H, m), 7,28 (1H, d, J= 9,0 Hz), 7,19 (1H, br t, J= 9,0 Hz), 5,26 (2H, s), 4,28 (2H, t, J= 6,0 Hz), 2,63 (2H, t, J= 6,0 Hz), 2,41 (4H, t, J= 4,8 Hz), 1,50 (4H, quin, J= 5,3 Hz), 1,45-1,35 (2H, m). Exemplo 2 Fórmula química 61
Figure img0065
(Etapa 1) Síntese de 4-(3-cloro-4-(3-fluorbenziloxi)fenilamino)-6-(2- (N-(t-butoxicarbonila)-N-etilamino)etiloxiimino)quinazolina (V-16)
[0192] Em tetrahidrofurano (1,5 ml) foram dissolvidos 4-(3-cloro- 4-(3-fluorbenziloxi)fenilamino)-6-formilquinazolina (IV-1, 120 mg) e N- (t-butoxicarbonila)etilaminoetoxiamina (110 mg), e 134 μl de 2 mol/l de ácido clorídrico foram adicionados, e em seguida a mistura foi agitada à temperatura ambiente por 4 horas. Depois de completada a reação, a mistura reacional foi despejada em solução aquosa saturada e gelada de bicarbonato de sódio, e extraída com acetato de etila. A camada orgânica foi lavada com água e solução aquosa de cloreto de sódio, secada em sulfato de magnésio, e concentrada. O resíduo resultante foi purificado por cromatografia de coluna de amino (eluindo com hexano: acetato de etila = 1:1), e ainda novamente purificado por cromatografia sobre sílica-gel (eluindo com hexano: acetato de etila = 1:1) para obter 4-(3-cloro-4-(3- fluorbenziloxi)fenilamino)-6-(2-(N-(t-butoxicarbonila)-N- etilamino)etiloxiimino)quinazolina (V-16, 96 mg) como um óleo viscoso amarelo. 1H RMN (d6-DMSO, δ): 9,93 (1H, s), 8,63 (1H, brs), 8,60 (1H, s), 8,34 (1H, s), 8,12 (1H, dd, J= 1,2 Hz, J= 9,0 Hz), 8,01 (1H, d, J= 2,4 Hz), 7,79 (1H, d, J= 8,4 Hz), 7,72 (1H, dd, J= 2,4 Hz, J= 8,4 Hz), 7,48 (1H, dt, J= 6,0 Hz, J= 8,1 Hz), 7,36-7,30 (2H, m), 7,28 (1H, d, J= 9,0 Hz), 7,23-7,14 (1H, m), 5,26 (2H, s), 4,26 (2H, t, J= 5,7 Hz), 3,50 (2H, t, J= 6,3 Hz), 3,23 (2H, q, J= 6,9 Hz), 1,38 (9H, s), 1,12-1,00 (3H, m).
[0193] O composto a seguir foi sintetizado da mesma maneira que para a primeira etapa acima. Fórmula química 62
Figure img0066
Tabela 3
Figure img0067
Figure img0068
Figure img0069
Figure img0070
Figure img0071
(Etapa 2) Síntese de 4-(3-cloro-4-(3-fluorbenziloxi)fenilamino)-6-(2-(Netilamino)etiloxiimino)quinazolina (V-17)
[0194] Em clorofórmio (1,8 ml) foi dissolvida 4-(3-cloro-4-(3- fluorbenziloxi)fenilamino)-6-(2-(N-(t-butoxicarbonila)-N- etilamino)etiloxiimino)quinazolina (V-16, 54 mg), e ácido trifluoracético (1,8 ml) foi adicionado, seguido de agitação à temperatura ambiente por 1 hora. Depois de completada a reação, a mistura reacional foi concentrada, e diluída com acetato de etila. A mistura foi seqüencialmente lavada com solução aquosa saturada de bicarbonato de sódio, água, e solução aquosa de cloreto de sódio, e secada em sulfato de magnésio. Depois de concentração, o resíduo cristalino foi lavado com uma mistura de diclorometano-hexano (1:4) para obter 4-(3- cloro-4-(3-fluorbenziloxi)fenilamino)-6-(2-(N- etilamino)etiloxiimino)quinazolina (V-17, 28 mg) como um sólido branco. 1H RMN (d6-DMSO, δ): 9,96 (1H, s), 8,65 (1H, brs), 8,60 (1H, s), 8,35 (1H, s), 8,11 (1H, d, J= 9,0 Hz), 8,01 (1H, d, J= 3,0 Hz), 7,80 (1H, d, J= 9,0 Hz), 7,75-7,70 (1H, m), 7,52-7,43 (1H, m), 7,36-7,31 (2H, m), 7,28 (1H, d, J= 9,3 Hz), 7,23-7,14 (1H, m), 5,26 (2H, s), 4,26 (2H, t, J= 6,0 Hz), 2,93 (2H, t, J= 6,0 Hz), 2,66 (2H, q, J= 7,2 Hz), 1,05 (3H, t, J= 7,2 Hz). Exemplo 3 Fórmula química 63
Figure img0072
(Etapa 1) Síntese de 4-(3-cloro-4-(3-fluorbenziloxi)fenilamino)-6-(1-(N- cianometilpirrolidin-2-il)metoxiimino)metilquinazolina (V-30)
[0195] Em 0,4 ml de N, N-dimetilacetamida foram dissolvidos 40 mg de composto V-29 e 8 μl de iodoacetonitrila, e 15 mg de carbonato de potássio foram adicionados, seguidos de agitação à temperatura ambiente por 1 hora. Depois da reação, solução aquosa saturada de cloreto de sódio foi adicionada, seguida de extração com acetato de etila. A camada orgânica foi desidratada sendo passada por um Presep (marca registrada), e o filtrado foi concentrado. O resíduo concentrado foi purificado por cromatografia sobre sílica-gel (eluindo com hexano: acetato de etila = 2:1) para obter 35 mg de 4-(3-cloro-4-(3- fluorbenziloxi)fenilamino)-6-(1-(N-cianometilpirrolidin-2- il)metoxiimino)metilquinazolina (V-30). 1H RMN (d6-DMSO, δ): 9,92 (1H, s), 8,62 (1H, d, J= 1,5 Hz), 8,58 (1H, s), 8,36 (1H, s), 8,09 (1H, dd, J= 8,7 Hz, J= 1,5 Hz), 7,99 (1H, d, J= 2,6 Hz), 7,78 (1H, d, J= 8,7 Hz), 7,71 (1H, dd, J= 9,0 Hz, J= 2,6 Hz), 7,49-7,42 (1H, m), 7,33-7,25 (3H, m), 7,16 (1H, dt, J= 8,1 Hz, J= 1,8 Hz), 5,24 (2H, s), 4,17 (2H, d, J= 5,7 Hz), 3,97 (1H, d, J= 17 Hz), 3,90 (1H, d, J= 17 Hz), 3,00-2,89 (2H, m), 2,01-1,89 (1H, m), 1,78-1,54 (3H, m). Exemplo 4 Fórmula química 64
Figure img0073
(Etapa 1) Síntese de 4-(3-cloro-4-(3-fluorbenziloxi)fenilamino)-6-(2-(4- acriloila-1-piperazin-1-ila)etoxiimino)metilquinazolina (V-43)
[0196] Em 1,5 ml de tetrahidrofurano foram dissolvidos 40 mg de composto V-42 e 6 μl de cloreto de acriloíla, seguido de agitação à temperatura ambiente por 2 horas. Depois da reação, solução aquosa saturada de cloreto de sódio foi adicionada, seguida de extração com acetato de etila. A camada orgânica foi desidratada sendo passada por CHEM ELUT (nome comercial), e o filtrado foi concentrado. O resíduo concentrado foi purificado por cromatografia (eluindo com acetato de etila contendo 1% metanol), e o resíduo resultante foi solidificado com hexano-acetato de etila (6:1) para obter 20 mg de 4-(3-cloro-4-(3- fluorbenziloxi)fenilamino)-6-(2-(4-acriloila-1-piperazin-1- ila)etoxiimino)metilquinazolina (V-43). 1H RMN (d6-DMSO, δ): 9,95 (1H, s), 8,64 (1H, s), 8,59 (1H, s), 8,35 (1H, s), 8,10 (1H, d, J= 8,7 Hz), 8,00 (1H, d, J= 2,4 Hz), 7,78 (1H, d, J= 8,7 Hz), 7,72 (1H, dd, J= 9,0 Hz, 2,7 Hz), 7,44-7,51 (1H, m), 7,26-7,35 (3H, m), 7,15-7,22 (1H, m), 6,79 (1H, dd, J= 16,5 Hz, 10,2 Hz), 6,10 (1H, dd, J= 16,5 Hz, 2,4 Hz), 6,17 (1H, dd, J= 10,5 Hz, 2,4 Hz), 5,26 (2H, s), 4,32 (2H, t, J= 5,7 Hz), 3,55 (4H, m), 2,72 (2H, t, J= 5,7 Hz), 2,50 (4H, m) Exemplo 5 Fórmula química 65
Figure img0074
(Etapa 1) Síntese de 4-(3-cloro-4-(3-fluorbenziloxi)fenilamino)-6-(2-(4-(2- metanosulfoniletila)-1-piperazin-1 -ila)etoxiimino)metilquinazolina (V-44)
[0197] Em 1 ml de tetrahidrofurano foram dissolvidos 25 mg de composto V-42 e 4 μl de metilvinilsulfona, seguido de agitação à temperatura ambiente por 21 horas. Além disso, 4 μl de metilvinilsulfona foram adicionados, seguidos de agitação à temperatura ambiente por 29 horas. Depois da reação, solução aquosa saturada de cloreto de sódio foi adicionada, seguida de extração com acetato de etila. A camada orgânica foi lavada seqüencialmente com água, e solução aquosa saturada de cloreto de sódio, e secada em sulfato de magnésio. O resíduo concentrado foi purificado por cromatografia (eluindo com acetato de etila) usando uma coluna de amina, e o resíduo resultante foi solidificado com hexano-acetato de etila (6:1) para obter 15 mg de 4-(3- cloro-4-(3-fluorbenziloxi)fenilamino)-6-(2-(4-(2-metanosulfoniletila)-1- piperazin-1-ila)etoxiimino)metilquinazolina (V-44). 1H RMN (d6-DMSO, δ): 9,95(1H, s), 8,63(1H, s), 8,59(1H, s), 8,34(1H, s), 8,10(1H, d, J= 9,6 Hz), 8,00 (1H, d, J= 2,4 Hz), 7,79 (1H, d, J= 8,4 Hz), 7,71 (1H, dd, J= 8,7 Hz, 2,7 Hz), 7,44-7,51 (1H, m), 7,26-7,34 (3H, m), 7,15-7,22 (1H, m), 5,26 (2H, s), 4,29 (2H, t, J= 6,0 Hz), 3,27 (2H, t, J= 6,6 Hz), 3,02 (3H, s), 2,67-2,70 (4H, m), 2,46 (8H, m)
[0198] O composto a seguir foi sintetizado de acordo com os mesmos métodos usados nos exemplos 1 a 5. Fórmula química 66
Figure img0075
Tabela 4
Figure img0076
Figure img0077
Figure img0078
Figure img0079
Figure img0080
Tabela 5
Figure img0081
Figure img0082
Figure img0083
Figure img0084
Figure img0085
Tabela 6
Figure img0086
Figure img0087
Figure img0088
Figure img0089
Figure img0090
Tabela 7
Figure img0091
Figure img0092
Figure img0093
Figure img0094
Tabela 8
Figure img0095
Figure img0096
Figure img0097
Figure img0098
Tabela 9
Figure img0099
Figure img0100
Figure img0101
Figure img0102
Tabela 10
Figure img0103
Figure img0104
Figure img0105
Tabela 11
Figure img0106
Figure img0107
(Etapa 1) Síntese de 4-(3-cloro-4-(3-fluorbenziloxi)fenilamino)-6-(4-(N- (2-(metanossulfonila)etila)-N-(2,2,2- trifluoracetila)amino)butiloxiimino)quinazolina (V-14)
[0199] Em N,N-dimetilacetamida (1,5 ml) foram dissolvidos 4-(3- cloro-4-(3-fluorbenziloxi)fenilamino)-6-(hidroxiimino)quinazolina (V-2, 84 mg) e N-(4-bromobutila)-N-(2-metanossulfoniletila)-2, 2, 2- trifluoracetamida (71 mg), e carbonato de potássio (41 mg) foi adicionado, seguido de agitação a 60°C por 13 horas com aquecimento. Em seguida, a mistura reacional foi despejada em ácido cítrico 0,5 M, seguida de extração com acetato de etila. A camada orgânica foi lavada com água e solução aquosa de cloreto de sódio, e secada em sulfato de magnésio. O produto bruto foi purificado por cromatografia sobre sílica-gel (eluindo com hexano: acetato de etila = 1:4) para obter 4-(3- cloro-4-(3-fluorbenziloxi)fenilamino)-6-(4-(N-(2-(metanossulfonila)etila)- 2, 2, 2-trifluoracetamido)butiloxiimino)quinazolina (V-14, 41 mg) como um sólido amarelo pálido. 1H RMN (d6-DMSO, δ): 9,94 (1H, s), 8,63 (1H, s), 8,59 (1H, s), 8,33 (1H, s), 8,10 (1H, dd, J= 8,4 Hz, J= 1,5 Hz), 8,00 (1H, d, J= 2,4 Hz), 7,78 (1H, d, J= 8,7 Hz), 7,71 (1H, dd, J= 2,3 Hz, J= 8,7 Hz), 7,47 (1H, dt, J= 6,0 Hz, J= 8,1 Hz), 7,36-7,31 (2H, m), 7,28 (1H, d, J= 9,0 Hz), 7,18 (1H, dt, J= 2,0 Hz, J= 8,6 Hz), 5,26 (2H, s), 4,26-4,18 (2H, m), 3,79 (2H, t, J= 7,1 Hz), 3,60-3,44 (4H, m), 3,05 (3H, s), 1,78-1,66 (4H, m).
(Etapa 2) Síntese de 4-(3-cloro-4-(3-fluorbenziloxi)fenilamino)-6-(4-(2- (metanossulfonila)etilamino)butiloxiimino)quinazolina (V-15)
[0200] Em 2,6 ml de uma mistura (1:1) de tetrahidrofurano e metanol foi dissolvida 4-(3-cloro-4-(3-fluorbenziloxi)fenilamino)-6-(4-(N-(2- (metanossulfonila)etila)-2, 2, 2-trifluoracetamido)butiloxiimino)quinazolina (V-14, 40 mg), e 86 μl de solução aquosa de hidróxido de sódio a 1 mol/l foram adicionados, seguido de agitação à temperatura ambiente por 14 horas, e a 40°C por 2 horas. Depois da reação, a mistura reacional foi extraída com acetato de etila, a camada orgânica foi secada, e o filtrado foi concentrado. O resíduo concentrado foi purificado por cromatografia (eluindo com acetato de etila contendo 0 a 3% metanol) usando uma coluna de amina, e o óleo amarelo pálido resultante foi pulverizado com uma mistura de hexano e acetato de etila para obter 4-(3-cloro-4-(3- fluorbenziloxi)fenilamino)-6-(4-(2- (metanossulfonila)etilamino)butiloxiimino)quinazolina (V-15, 12 mg) como um sólido amarelo pálido. 1H RMN (d6-DMSO, δ): 9,95 (1H, s), 8,63 (1H, s), 8,59 (1H, s), 8,33 (1H, s), 8,11 (1H, d, J= 8,7 Hz), 8,01 (1H, d, J= 2,4 Hz), 7,79 (1H, d, J= 8,7 Hz), 7,72 (1H, br d, J= 9,0 Hz), 7,51-7,44 (1H, m), 7,36-7,31 (2H, m), 7,28 (1H, d, J= 9,0 Hz), 7,19 (1H, br t, J= 9 Hz), 5,26 (2H, s), 4,20 (2H, t, J= 6,6 Hz), 3,21 (2H, t, J= 6,9 Hz), 2,91 (2H, t, J= 6,6 Hz), 2,56 (2H, t, J= 6,9 Hz), 1,73 (2H, quin, J= 7 Hz), 1,51 (2H, quin, J= 7 Hz). Exemplo 7 Fórmula química 68
Figure img0108
Figure img0109
VIII-1
(Etapa 1) Síntese de 4-(3-cloro-4-(3-fluorbenziloxi)fenilamino)-6-(1- hidroxietan-1-ila)quinazolina (VI-1)
[0201] Em 30 ml de tetrahidrofurano foram dissolvidos 620 mg de 4-(3-cloro-4-(3-fluorbenziloxi)fenilamino)-6-formilquinazolina (IV-1), a solução foi resfriada para 0°C em uma atmosfera de nitrogênio, e 4,9 ml de brometo de metilmagnésio (solução em tetrahidrofurano 0,93 M) foram adicionados em gotas. Depois da reação a 0°C por 1 hora em uma atmosfera de nitrogênio, água e acetato de etila foram adicionados para separar as camadas. A camada orgânica foi lavada sequencialmente com água e solução aquosa saturada de cloreto de sódio, e secada em sulfato de magnésio. Depois de concentração, o cristal resultante foi lavado com clorofórmio para obter 330 mg de 4- (3-cloro-4-(3-fluorbenziloxi)fenilamino)-6-(1-hidroxietan-1- ila)quinazolina (VI-1). 1H RMN (d6-DMSO δ): 9,81 (1H, s), 8,55 (1H, s), 8,44 (1H, s), 8,03 (1H, d, J= 2,4 Hz), 7,86 (1H, dd, J= 8,7 Hz, J= 1,2 Hz), 7,787,73 (2H, m), 7,51-7,44 (1H, m), 7,35-7,25 (3H, m), 7,18 (1H, dt, J= 8,4 Hz, J= 2,4 Hz), 5,44 (1H, d, J= 3,9 Hz), 5,26 (2H, s), 4,93 (1H, m), 1,45 (3H, d, J= 6,6 Hz)
(Etapa 2) Síntese de 4-(3-cloro-4-(3-fluorbenziloxi)fenilamino)-6- (etano-4-ona)quinazolina (VII-1)
[0202] Em 150 ml de tetrahidrofurano foram dissolvidos 360 mg de 4-(3-cloro-4-(3-fluorbenziloxi)fenilamino-6-(1-hidroxietan-1- ila)quinazolina (VI-1), e 3,7 g de dióxido de manganês foram adicionados, seguido de agitação à temperatura ambiente por uma noite. Depois da reação, as substâncias inorgânicas foram filtradas, e o filtrado foi concentrado. O cristal resultante foi lavado com clorofórmio para obter 320 mg de 4-(3-cloro-4-(3- fluorbenziloxi)fenilamino)-6-(etano- 4-ona)quinazolina (VII-1). 1H RMN (d6-DMSO δ): 10,18 (1H, s), 9,16 (1H, d, J= 1,5 Hz), 8,64 (1H, s), 8,31 (1H, dd, J= 8,4 Hz, J= 2,4 Hz), 7,97 (1H, d, J= 2,4 Hz), 7,83 (1H, d, J= 8,7 Hz), 7,71 (1H, dd, J= 8,7 Hz, J= 2,4 Hz), 7,51-7,44 (1H, m), 7,35-7,29 (3H, m), 7,19 (1H, dt, J= 8,1 Hz, J= 2,7 Hz), 5,27 (2H, s), 2,74 (3H, s)
[0203] Os compostos a seguir foram sintetizados da mesma maneira que aquela descrita na primeira etapa e na segunda etapa acima. Fórmula química 69
Figure img0110
Tabela 12 Fórmula química 70
Figure img0111
Figure img0112
Figure img0113
Tabela 13
Figure img0114
Figure img0115
Figure img0116
>Tabela 14
Figure img0117
Figure img0118
(Etapa 3) Síntese de 4-(3-cloro-4-(3-fluorbenziloxi)fenilamino)-6-(1-(2- (1-morfolino)etoxiimino)etila)quinazolina (VIII-1)
[0204] Em 6 ml (20:1) de uma mistura de tetrahidrofurano e água foram dissolvidos 100 mg de composto VII-1 e 78 mg de dicloridrato de 2-(1-morfolino)etoxiamina, seguido de agitação à temperatura ambiente por uma noite. A mistura reacional foi diluída com acetato de etila, lavada com solução aquosa saturada de bicarbonato de sódio, e secada em sulfato de magnésio. Depois de concentração, o sólido foi lavado com uma mistura (2:1) de hexano e acetato de etila para obter 72 mg de 4- (3-cloro-4-(3-fluorbenziloxi)fenilamino)-6-(1-(2-(1- morfolino)etoxiimino)etila)quinazolina (VIII-1). 1H RMN (d6-DMSO, δ): 9,93 (1H, s), 8,62 (1H, brs), 8,58 (1H, s), 8,22 (1H, d, J= 6,6 Hz), 7,96 (1H, d, J= 1,8 Hz), 7,76 (1H, d, J= 6,6 Hz), 7,70 (1H, dd, J= 6,6 Hz, J= 1,8 Hz), 7,51-7,45 (1H, m), 7,35-7,28 (3H, m), 7,19 (1H, t, J= 6,0 Hz), 5,27 (2H, s), 4,33 (2H, t, J= 6,0 Hz), 3,59 (4H, t, J= 4,5 Hz), 2,69 (2H, t, J= 6,0 Hz), 2,47 (4H, t, J= 4,5 Hz), 2,36 (3H, s)
Exemplo de referência 1
[0205] Como um método para obter um derivado tipo cetona (VII), o método a seguir é exemplificado além da primeira etapa e da segunda etapa do exemplo 7. Fórmula química 71
Figure img0119
(Etapa 1) Síntese de éster metílico do ácido 4-(3-cloro-4-(3- fluorbenziloxi)fenilamino)-quinazolina-6-carboxílico (X-1)
[0206] Em uma mistura de 200 ml de dimetilformamida e 200 ml de metanol foram dissolvidos cloridrato de 4-(3-cloro-4-(3- fluorbenziloxi)fenilamino)-6-iodoquinazolina (III-1, 20 g) e 1,29 g de diclorobis(trifenilfosfina)paládio, e 25,7 ml de trietilamina foram adicionados. O interior de um vaso de reação foi suficientemente substituído com um gás monóxido de carbono, seguido de uma reação a 80°C por 15 horas sob a atmosfera de monóxido de carbono. A mistura reacional foi filtrada por Celite, e o filtrado foi resfriado para 0°C com agitação. Um precipitado foi filtrado, lavado com metanol frio, e secado para obter éster metílico do ácido 4-(3-cloro-4-(3- fluorbenziloxi)fenilamino)quinazolina-6-carboxílico (X-1, 13,5 g) como um sólido incolor. 1H RMN (d6-DMSO, δ): 10,26 (1H, s), 9,25 (1H, d, J= 1,5 Hz), 8,65 (1H, s), 8,31 (1H, dd, J= 1,5 Hz, J= 8,7 Hz), 8,02 (1H, d, J= 2,7 Hz), 7,85 (1H, d, J= 2,7 Hz), 7,77 (1H, dd, J= 2,7 Hz, J= 8,7 Hz), 7,49-7,44 (1H, m), 7,35-7,27 (3H, m), 7,20-7,16 (1H, m), 5,27 (2H, s), 3,96 (3H, s).
(Etapa 2) Síntese de metóxi metila amida de ácido 4-(3-cloro-4-(3- fluorbenziloxi)fenilamino)quinazolina-6-carboxílico (XI-1)
[0207] Em tetrahidrofurano (230 ml) foi dissolvido o éster metílico do ácido 4-(3-cloro-4-(3-fluorbenziloxi)fenilamino)-quinazolina-6- carboxílico (X-1, 11,6 g), cloridrato de N, O-dimetilhidroxilamina (7,8 g) foi adicionado, e solução de iPrMgCl a 2 mol/l em tetrahidrofurano (79,8 ml) foi adicionada em gotas por 30 minutos com resfriamento em gelo. Depois de completada a adição, a mistura foi agitada por 20 minutos com resfriamento em gelo e, depois de completada a reação, 200 ml de solução aquosa saturada de cloreto de amônio foram adicionados. Depois que 100 ml de água foram adicionados à mistura, a mistura foi extraída com acetato de etila, e a camada orgânica foi secada em sulfato de sódio. O filtrado foi concentrado para obter metóxi metila amida de ácido 4-(3-cloro-4-(3-fluorbenziloxi)fenilamino)-quinazolina-6- carboxílico (XI-1, 12,7 g) como um sólido amarelo pálido. 1H RMN (d6-DMSO, δ): 10,01 (1H, s), 8,79 (1H, d, J= 1,5 Hz), 8,64 (1H, s), 8,05 (1H, d, J= 2,7 Hz), 8,00 (1H, dd, J= 1,5 Hz, J= 8,7 Hz), 7,81 (1H, d, J= 8,7 Hz), 7,76 (1H, dd, J= 2,7 Hz, J= 8,7 Hz), 7,52-7,44 (1H, m), 7,35-7,26 (3H, m), 7,22-7,16 (1H, m), 5,27 (2H, s), 3,57 (3H, s), 3,34 (3H, s).
(Etapa 3) Síntese de 4-(3-cloro-4-(3-fluorbenziloxi)fenilamino)-6-(1-oxo- 2-butin-1-ila)quinazolina (VII-4)
[0208] A uma solução de 4,22 ml de N,N-diisopropilamina em tetrahidrofurano (25 ml) resfriada para -78°C foram adicionados em gotas 18,8 ml de solução de n-BuLi a 1,6 mol/l em hexano. Depois de completada a adição, a temperatura foi aumentada para 0°C, e a mistura foi agitada a 0°C por 20 minutos, e novamente resfriada para -78°C. 1,33 ml de 2-bromo-1-propeno em tetrahidrofurano (25 ml) foi adicionado, e a mistura foi agitada a -78°C por 2 horas. À mistura foi adicionada em gotas uma solução de metóxi metila amida de ácido 4- (3-cloro-4-(3-fluorbenziloxi)fenilamino)-quinazolina-6-carboxílico (XI-1, 2,33 g) em tetrahidrofurano (50 ml) e, depois de completada a adição, a temperatura foi aumentada para 0°C, seguido de agitação por 3 horas. Depois de completada a reação, a mistura reacional foi despejada em água gelada, neutralizada com ácido clorídrico a 2 mol/l, e extraída com acetato de etila. A camada orgânica foi secada em sulfato de sódio, o filtrado foi concentrado, e o resíduo cristalino resultante foi lavado com cloreto de metileno para obter 4-(3-cloro-4-(3-fluorbenziloxi)fenilamino)- 6-(1-oxo-2-butin-1-ila)quinazolina (VII-4, 1,71 g) como um sólido amarelo.
Exemplo de referência 2
[0209] Como outro método da terceira etapa do Exemplo de referência 1, temos o seguinte método. Fórmula química 72
Figure img0120
(Etapa 3) Síntese de 4-(3-cloro-4-(3-fluorbenziloxi)fenilamino)-6-(1-oxo- 2-propino-3-ciclopropila-1-ila)quinazolina (VII-7)
[0210] A uma solução de 0,16 ml de etinilciclopropano em tetrahidrofurano (3 ml) resfriada para -78°C foi adicionado em gotas 1,25 ml de solução de n-BuLi a 1,54 mol/l em hexano. Depois de completada a adição, a mistura foi agitada a -78°C por 1 hora. À mistura foi adicionada em gotas uma solução de metóxi metila amida de ácido 4- (3-cloro-4-(3-fluorbenziloxi)fenilamino)-quinazolina-6-carboxílico (XI-1, 300 mg) em tetrahidrofurano (3 ml) e, depois de completada a adição, a temperatura foi aumentada para 0°C, e a mistura foi agitada por 3 horas. Depois de completada a reação, 10 ml de água e 10 ml de acetato de etila foram adicionados à mistura reacional para separar as camadas. Depois que a camada aquosa foi novamente extraída com 10 ml de acetato de etila duas vezes, todas as camadas orgânicas foram combinadas, e secadas em sulfato de sódio, e o filtrado foi concentrado. O resíduo foi purificado por cromatografia de coluna sobre sílica-gel para obter 4-(3-cloro-4-(3-fluorbenziloxi)fenilamino)-6-(1-oxo-2-propino- 3-ciclopropila-1-ila)quinazolina) (VII-7, 265 mg) como um sólido amarelo. 1H RMN (d6-DMSO, δ): 10,4 (1H, s), 9,21 (1H, s), 8,67 (1H, s), 8,41 (1H, d, J= 8,7 Hz), 8,01 (1H, d, J= 2,7 Hz), 7,88 (1H, d, J= 8,7 Hz), 7,73 (1H, dd, J= 8,7 Hz, J= 3 Hz), 7,40-7,52 (1H, m), 7,15-7,4 (4H, m), 5,28 (2H, s), 1,77-1,87 (1H, m), 1,05-1,20 (3H, m).
Exemplo de referência 3
[0211] Como um método para obter um derivado tipo amida (XI), temos o método a seguir além da primeira etapa e da segunda etapa do Exemplo de referência 1. Fórmula química 73
Figure img0121
(Etapa 1) Síntese de éster metílico do ácido 4-hidroxiquinazolina-6- carboxílico (XII-1)
[0212] 4-Hidroxi-6-iodoquinazolina (250 mg), uma quantidade catalítica de acetato de paládio (II) e 1,3-bis(difenilfosfino)propano foram dissolvidos em N,N-dimetilformamida (3,8 ml) e metanol (1,5 ml) e 1,5 ml de trietilamina foi adicionado. Depois que o interior de um vaso de reação foi suficientemente substituído com gás monóxido de carbono, uma reação foi realizada a 80°C por 20 horas sob atmosfera de monóxido de carbono. Depois de completada a reação, a mistura reacional foi despejada em ácido cítrico aquoso a 10%, seguida de extração com acetato de etila. A camada orgânica foi lavada com água, e secada em sulfato de sódio, e o filtrado foi concentrado. O resíduo resultante foi purificado por cromatografia de coluna sobre sílica-gel (eluindo com acetato de etila) para obter éster metílico do ácido 4- hidroxiquinazolina-6-carboxílico (XII-1, 157 mg) como um sólido castanho. 1H RMN (d6-DMSO, δ): 12,48 (1H« s), 8,63 (1H, s), 8,26 (1H, d, J= 8,4 Hz), 8,19 (1H, s), 7,73 (1H, d, J= 8,4 Hz).
(Etapa 2) Síntese de metoximetilamida de ácido 4-hidroxiquinazolina-6- carboxílico (XIII-1)
[0213] Éster metílico do ácido 4-Hidroxiquinazolina-6-carboxílico (XII-1, 4,0 g) foi dissolvido em tetrahidrofurano (120 ml), cloridrato de N,O-dimetila hidroxilamina (5,7 g) foi adicionado, e solução de iPrMgCl a 2 mol/l em tetrahidrofurano (59 ml) foi adicionada em gotas durante 30 minutos. Depois de completada a adição, a mistura foi agitada por 30 minutos com resfriamento em gelo e, depois de completada a reação, 40 ml de ácido clorídrico a 2 mol/l foram adicionados em gotas. A mistura foi neutralizada com solução aquosa saturada de bicarbonato de sódio, e extraída com clorofórmio, e a camada orgânica foi lavada com solução aquosa de cloreto de sódio, e secada em sulfato de sódio. Depois de concentração, o resíduo cristalino foi purificado por cromatografia de coluna sobre sílica-gel (eluindo com acetato de etila: metanol = 9:1) para obter metoximetilamida de ácido 4-hidroxiquinazolina-6-carboxílico (XIII-1, 2,9 g) como um sólido branco. 1H RMN (d6-DMSO, δ): 12,42 (1H, s), 8,36 (1H, s), 8,18 (1H, s), 8,02 (1H, d, J= 8,4 Hz), 7,73 (1H, d, J= 8,4 Hz), 3,57 (3H, s), 3,32 (3H, s).
(Etapa 3) Síntese de metoximetilamida de ácido 4-cloroquinazolina-6- carboxílico (XIV-1)
[0214] Metoximetilamida de ácido 4-Hidroxiquinazolina-6- carboxílico (XIII-1, 2,9 g) foi suspendida em tolueno (57 ml), e 6,8 ml de trietilamina e 3,4 ml de oxicloreto de fósforo foram adicionados, seguido de agitação a 130°C por 30 minutos. Depois de completada a reação, a mistura reacional foi resfriada para a temperatura ambiente, e 50 ml de solução aquosa saturada de bicarbonato de sódio e acetato de etila foram adicionados. Bicarbonato de sódio foi adicionado até a camada aquosa apresentar um pH 8, seguido de extração com acetato de etila. A camada orgânica foi lavada com solução aquosa saturada de bicarbonato de sódio, secada em sulfato de sódio. Depois de concentração, o resíduo cristalino foi lavado com éter dietílico, e secado para obter metoximetilamida de ácido 4-cloroquinazolina-6-carboxílico (XIV-1, 2,3 g) como um sólido branco. 1H RMN (d6-DMSO, δ): 8,75 (1H, s), 8,36 (1H, s), 8,11 (1H, dd, J= 2,0 Hz, J= 8,4 Hz), 7,87 (1H, d, J= 8,4 Hz), 3,56 (3H, s), 3,32 (3H, s).
(Etapa 4) Síntese de metoximetilamida de ácido 4-(3-cloro-4-(piridin-2- ilmetoxi)fenilamino)-quinazolina-6-carboxílico (XI-2)
[0215] Metoximetilamida de ácido 4-Cloroquinazolina-6-carboxílico (XIV-1, 5,78 g) foi dissolvida em tetrahidrofurano (100 ml), e 5,39 g de 3-cloro-4-(piridin-2-ilmetoxi)anilina foram adicionados, seguido de agitação a 60°C por 1 hora. Um precipitado foi filtrado, e lavado com tetrahidrofurano para obter metoximetilamida de ácido 4-(3-cloro-4- (piridin-2-ilmetoxi)fenilamino)-quinazolina-6-carboxílico (XI-2, 7,87 g) como um sólido branco. O filtrado foi deixado repousar à temperatura ambiente, e o precipitado resultante foi recolhido por filtração, para de novo obter 2,21 g de XI-2. 1H RMN (d6-DMSO, δ): 10,02 (1H, s), 8,79 (1H, s), 8,62-8,59 (2H, m), 8,04 (1H, s), 8,00-7,98 (1H, m), 7,90-7,86 (1H, s), 7,80-7,78 (1H, m), 7,75-7,73 (1H, m), 7,59-7,57 (1H, m), 7,37-7,35 (1H, m), 7,28- 7,26 (1H, m), 5,29 (2H, s), 3,57 (3H, s). Fórmula química 74
Figure img0122
Exemplo de referência 4
[0216] Como outro método da quarta etapa do Exemplo de referência 3, temos o método a seguir.
(Etapa 4) Síntese de metoximetilamida de ácido 4-(4- benzenossulfonilfenilamino)-quinazolina-6-carboxílico (XI-3)
[0217] Metoximetilamida de ácido 4-Cloroquinazolina-6-carboxílico (XIV-1, 550 mg), 611 mg de 4-benzenossulfonilfenilamina, 49 mg de acetato de paládio (II), 190 mg de Xant phos e 997 mg de carbonato de césio foram adicionados a 1, 4-dioxano (30 ml), e o interior de um vaso de reação foi substituído com nitrogênio gasoso, seguido de agitação a 100°C por 2,5 horas. A mistura reacional foi filtrada com Celite, e água foi adicionada ao filtrado, seguida de extração com acetato de etila. A camada orgânica foi lavada com solução aquosa saturada de cloreto de sódio, e secada em sulfato de sódio. O filtrado foi concentrado, e o resíduo foi purificado por cromatografia de coluna sobre sílica-gel (eluindo com acetato de etila: metanol = 95:5) para obter metoximetilamida de ácido 4-(4-benzenossulfonilfenilamino)- quinazolina-6-carboxílico (XI-3, 651 mg) como um sólido amarelo pálido. 1H RMN (d6-DMSO, δ): 10,66 (1H, s), 9,29 (1H, s), 8,80 (1H, s), 8,48 (1H, d, J= 7,7 Hz), 8,16 (2H, d, J= 7,7 Hz), 7,99-7,94 (5H, m), 7,80-7,61 (3H, m), 2,27 (3H, s).
Exemplo de referência 5
[0218] Como um método para obter um derivado tipo amida (XI), temos ainda o método a seguir além da primeira etapa e da segunda etapa do Exemplo de referência 1, e do Exemplo de referência 3. Fórmula química 75
Figure img0123
(Etapa 1) Síntese de metoximetilamida de ácido 4-(3-cloro-4-(3- fluorbenziloxi)fenilamino)-quinazolina-6-carboxílico (XI-1)
[0219] Cloridrato de 4-(3-Cloro-4-((3-fluorbenziloxi)fenilamino)-6- iodoquinazolina (III-1, 500 mg), 32 mg de diclorobis(trifenilfosfina)paládio, e 191 mg de N-hidroxissuccinimida foram dissolvidos em 10 ml de dimetilformamida, e 360 μl de trietilamida foram adicionados. O interior de um vaso de reação foi suficientemente substituído como gás monóxido de carbono, seguido de uma reação a 80°C por 3 horas sob atmosfera de monóxido de carbono. A 1/5 da mistura reacional foi adicionado 0,3 ml de uma solução aquosa de N,O- dimetilhidroxilamina a 40%, seguido de agitação à temperatura ambiente por uma noite. Depois de completada a reação, água foi adicionada à mistura reacional, seguida de extração com acetato de etila. A camada orgânica foi lavada com água e solução aquosa saturada de cloreto de sódio nesta ordem, e secada em sulfato de sódio. O resíduo concentrado do filtrado foi purificado por cromatografia de coluna sobre sílica-gel (eluindo com acetato de etila) para obter metoximetilamida de ácido 4-(3-cloro-4-(3-fluorbenziloxi)fenilamino)- quinazolina-6-carboxílico (XI-1, 74 mg) como um sólido amarelo pálido. Exemplo 8 Fórmula química 76
Figure img0124
(Etapa 1) Síntese de dicloridrato de 4-(3-cloro-4-(3- fluorbenziloxi)fenilamino)-6-( 1 -((S)-morfolin-2-ilmetoxiimino)-2-butin-1- ila)quinazolina (VIII-32)
[0220] A uma suspensão de 4-(3-cloro-4-(3- fluorbenziloxi)fenilamino)-6-(1-oxo-2-butin-1-ila)quinazolina (VII-4, 786 mg) e 614 mg de éster ter-butílico do ácido (S)-2-aminooximetila- morfolina-4-carboxílico em 31 ml de 1,4-dioxano foram adicionados 2,21 ml de solução aquosa de ácido metanossulfônico a 2 mol/l, seguidos de agitação a 80°C por 22 horas. E, 1,32 ml de solução aquosa de ácido metanossulfônico a 2 mol/l foi adicionalmente adicionado, seguido de mais agitação por 5,5 horas. Depois de completada a reação, a mistura reacional foi despejada em solução aquosa de bicarbonato de sódio, seguida de extração com acetato de etila. Depois que uma camada aquosa foi novamente extraída com acetato de etila, todas as camadas orgânicas foram combinadas, lavadas com água, e secadas em sulfato de magnésio anidro. Depois que o filtrado foi concentrado, o resíduo foi purificado por cromatografia de coluna sobre sílica-gel (eluindo com clorofórmio: metanol = 9:1) para obter um óleo amarelo. Este óleo foi dissolvido em 50 ml de acordo com, e filtrado, e 0,95 ml de solução de ácido clorídrico a 4 mol/l em acetato de etila foi adicionada com agitação, seguida de agitação à temperatura ambiente por 1 hora. Um precipitado foi filtrado, e lavado com acetato de etila e hexano nesta ordem. Uma substância recolhida por filtração foi recristalizada com metanol-acetato de etila para obter dicloridrato de 4-(3-cloro-4-(3- fluorbenziloxi)fenilamino)-6-(1-((S)-morfolin-2-ilmetoxiimino)-2-butin-1- ila)quinazolina (VIII-32, 839 mg) como um cristal amarelo. 1H RMN (d6-DMSO, δ): 11,69 (1H, bs), 9,49-9,37 (2H, m), 9,05 (1H, s), 8,88 (1H, s), 8,38 (1H, dd, J= 1,5 Hz, J= 8,7 Hz), 7,96 (1H, d, J= 8,7 Hz), 7,89 (1H, d, J= 2,7 Hz), 7,64 (1H, dd, J= 2,4 Hz, J= 9,0 Hz), 7,52-7,45 (1H, m), 7,36-7,30 (3H, m), 7,23-7,16 (1H, m), 5,31 (2H, s), 4,36-4,34 (1H, m), 4,25-4,22 (1H, m), 4,04-3,98 (1H, m), 3,84-3,77 (1H, m), 3,04-2,85 (3H, m), 2,28 (3H, s). Exemplo 9 Fórmula química 77
Figure img0125
(Etapa 1) Síntese de 4-(3-cloro-4-(3-fluorbenziloxi)fenilamino)-6-(1-(2- hidroxietoxiimino)-2-butin-1-ila)quinazolina (VIII-33)
[0221] 4-(3-Cloro-4-(3-fluorbenziloxi)fenilamino)-6-(1-oxo-2-butin-1- ila)quinazolina (VII-4, 10 g) foi dissolvida em 300 ml de 1,4-dioxano, 1,5 equivalente de 2-(acetoxi)etoxiamina foi adicionado, e 28 ml de solução aquosa de ácido metanossulfônico a 2 mol/l foram adicionados, seguidos de agitação a 60°C por 17 horas. A mistura reacional foi despejada em solução aquosa saturada de bicarbonato de sódio, e a mistura foi extraída com acetato de etila. A camada orgânica foi lavada com água, e secada em sulfato de sódio. O resíduo obtido por concentração do filtrado foi recristalizado de etanol hidratado-água, filtrado, e secado para obter 4-(3-cloro-4-(3-fluorbenziloxi)fenilamino)-6- (1-(2-hidroxietoxiimino)-2-butin-1-ila)quinazolina (VIII-33, 7,6 g) como um sólido incolor. 1H RMN (d6-DMSO, δ): 10,07 (1H, s), 8,74 (1H, s), 8,58 (1H, s), 8,22 (1H, d, J= 8,8 Hz), 7,96 (1H, d, J= 2,4 Hz), 7,80 (1H, d, J= 8,8 Hz), 7,69 (1H, dd, J= 2,4 Hz, J= 8,8 Hz), 7,50-7,45 (1H, m), 7,35-7,24 (3H, m), 7,20-7,16 (1H, m), 5,27 (2H, s), 4,79 (1H, t. J= 5,6 Hz), 4,29 (2H, t. J= 5,6 Hz), 3,75 (2H, dd, J= 5,2 Hz, J= 10,4 Hz), 2,26 (3H, s).
(Etapa 2) Síntese de 4-(3-cloro-4-(3-fluorbenziloxi)fenilamino)-6-(1-(2- sulfoniloxietoxiimino)-2-butin-1-ila)quinazolina (VIII-34)
[0222] 4-(3-Cloro-4-(3-fluorbenziloxi)fenilamino)-6-(1-(2- hidroxietoxiimino)-2-butin-1-ila)quinazolina (VIII-33, 7,6 g) foi dissolvida em 150 ml de tetrahidrofurano, e 4,19 ml de trietilamina e 2,33 ml de cloreto de metanossulfonila foram adicionados, seguidos de agitação por 3,5 horas. Depois de completada a reação, a mistura reacional foi despejada em água, e solução aquosa saturada de bicarbonato de sódio foi adicionada, seguida de extração com acetato de etila. A camada orgânica foi secada em sulfato de sódio, e o filtrado foi concentrado. Acetato de etila foi adicionado ao resíduo concentrado, este foi deixado repousar à temperatura ambiente, um cristal foi precipitado, e diluído com hexano, e o cristal foi recolhido por filtração para obter 4-(3-cloro- 4-(3-fluorbenziloxi)fenilamino)-6-(1-(2-sulfoniloxietoxiimino)-2-butin-1- ila)quinazolina (VIII-34, 7,66 g) como um cristal amarelo pálido. 1H RMN (d6-DMSO, δ): 10,07 (1H, s), 8,77 (1H, s), 8,60 (1H, s), 8,24 (1H, d, J= 8,8 Hz), 7,97 (1H, d, J= 2,4 Hz), 7,81 (1H, d, J= 8,8 Hz), 7,69 (1H, dd, J= 2,4 Hz, J= 8,8 Hz), 7,51-7,45 (1H, m), 7,35-7,27 (3H, m), 7,21-7,17 (1H, m), 5,27 (2H, s), 4,58 (2H, t. J= 4,8 Hz), 4,54 (2H, t. J= 4,8Hz), 3,24 (3H, s), 2,27 (3H, s). Fórmula química 78
Figure img0126
4-(3-Cloro-4-(piridin-2-ilmetoxi)fenilamino)-6-(1-(2- sulfoniloxietoxiimino)-2-butin-1-ila)quinazolina (VIII-36)
[0223] O composto foi sintetizado da mesma maneira que a descrita para a primeira etapa e para a segunda etapa. 1H RMN (d6-DMSO, δ): 10,09 (1H, s), 8,77 (1H, s), 8,61 (1H, s), 8,59 (1H, s), 8,24 (1H, d, J= 8,1 Hz), 7,97 (1H, d, J= 2,4 Hz), 7,89 (1H, t, J= 7,5 Hz), 7,81 (1H, d, J= 9,0 Hz), 7,68 (1H, dd, J= 2,4 Hz, J= 9,0 Hz), 7,59 (1H, d, J= 8,1 Hz), 7,40-7,35 (1H, m), 7,29 (1H, d, J= 9,0 Hz), 5,31 (2H, s), 4,57 (2H, bs), 4,55 (2H, bs), 3,24 (3H, s), 2,27 (3H, s). Fórmula química 79
Figure img0127
4-( 1 -(3-Fluorbenzila)-1 H-indazol-5-ilamino)-6-( 1 -(2-sulfoniloxietoxiimino)-2- butin-1-ila)quinazolina (VIII-37)
[0224] O composto foi sintetizado da mesma maneira que a descrita para a primeira etapa e para a segunda etapa. 1H RMN (d6-DMSO, δ): 10,20 (1H, s), 8,81 (1H, s), 8,53 (1H, s), 8,24 (1H, d, J= 8,7 Hz), 8,17 (1H, s), 8,13 (1H, s), 7,80 (1H, d, J= 8,7 Hz), 7,75 (1H, d, J= 8,7 Hz), 7,67 (1H, d, J= 9,3 Hz), 7,41-7,36 (1H, m), 7,147,04 (3H, m), 5,72 (2H, s), 4,58 (2H, t. J= 5,4 Hz), 4,54 (2H, t. J= 5,4 Hz), 3,24 (3H, s), 2,26 (3H, s).
(Etapa 3) Síntese de 4-(3-cloro-4-3-fluorbenziloxi)fenilamino)-6-(1-2- etilaminoetoxiimino)-2-butin-1-ila)quinazolina (VIII-35)
[0225] 4-(3-Cloro-4-(3-fluorbenziloxi)fenilamino)-6-(1-(2- sulfoniloxietoxiimino)-2-butin-1-ila)quinazolina (VIII-34, 100 mg) foi dissolvida em 3 ml de N,N-dimetilformamida, e 160 μg de solução aquosa de etilamina a 70% foram adicionados, seguidos de agitação a 60°C por 14 horas. Água foi adicionada à mistura reacional, seguida de extração com acetato de etila. A camada orgânica foi secada em sulfato de magnésio, e o resíduo concentrado do filtrado foi purificado por cromatografia (eluindo com acetato de etila) usando uma coluna de amina para obter 4-(3-cloro-4- 3-fluorbenziloxi)fenilamino)-6-(1-(2-etilaminoetoxiimino)-2-butin-1- ila)quinazolina (VIII-35, 53 mg) como um sólido incolor. 1H RMN (d6-DMSO, δ): 10,08 (1H, s), 8,74 (1H, s), 8,59 (1H, s), 8,21 (1H, d, J= 8,4 Hz), 7,96 (1H, s), 7,80 (1H, d, J= 8,8 Hz), 7,69 (1H, d, J= 8,0 Hz), 7,51-7,45 (1H, m), 7,35-7,27 (3H, m), 7,21-7,16 (1H, m), 5,27 (2H, s), 4,31 (2H, t. J= 5,6 Hz), 2,89 (2H, t, J= 6,0 Hz), 2,61 (2H, q, J= 7,2 Hz), 2,26 (3H, s), 1,02 (3H, t, J= 7,6 Hz).
[0226] Na aminação de uma terceira etapa, pode ser usada uma amina que está comercialmente disponível ou uma amina que pode ser sintetizada de acordo com o método descrito em J. Syn. Org. Chem., Jpn., 2001, 59:779-789, Tetrahedron Lett., 1995, 36:6373-6374, Synlett, 1999:1301-1303, Tetrahedron, 2002, 58:6267-6276 ou um sal da mesma. Exemplo 10 Fórmula química 80
Figure img0128
Figure img0129
(Etapa 1) Síntese de 4-(3-Cloro-4-hidroxifenilamino)-6-iodoquinazolina ÍIH-4)
[0227] Da mesma maneira que para a primeira etapa do Exemplo 1 e usando 20,3 g de 4-cloro-6-iodoquinazolina e 10 g de 3-cloro-4- hidroxianilina, cloridrato de 4-(3-cloro-4-hidroxifenilamino)-6- iodoquinazolina (III-4, 26,6 g) foi obtido como um sólido amarelo. 1H RMN (d6-DMSO, δ): 11,4 (1H, s), 10,5 (1H, s), 9,21 (1H, s), 8,93 (1H, s), 8,35 (1H, d, J= 8,4 Hz), 7,79 (1H, s), 7,69 (1H, d, J= 9,0 Hz), 7,48 (1H, d, J= 9,0 Hz), 7,10 (1H, d, J= 8,4 Hz).
(Etapa 2) Síntese de 4-(3-cloro-4-triisopropilsililoxifenilamino)-6- iodoquinazolina (III-5)
[0228] Cloridrato de 4-(3-Cloro-4-3-fluorbenziloxi)fenilamino)-6- iodoquinazolina (III-4, 20 g), 13,3 g de cloreto de triisopropilsilano, e 12,6 g de imidazol foram dissolvidos em 200 ml de N, N-dimetilformamida, seguidos de agitação à temperatura ambiente por 4 horas. Depois de completada a reação, 200 ml de solução aquosa saturada de bicarbonato de sódio e 200 ml de acetato de etila foram adicionados para separar as camadas. A camada aquosa foi novamente extraída com 200 ml de acetato de etila duas vezes, e todas as camadas orgânicas foram combinadas, lavadas com água e solução aquosa saturada de cloreto de sódio nesta ordem, e secadas em sulfato de magnésio anidro. O filtrado foi concentrado, e o resíduo foi lavado com hexano-acetato de etila (2:1) para obter 4-(3-cloro-4- triisopropilsililoxifenilamino)-6-iodoquinazolina (III-5, 25,3 g) como um sólido incolor. 1H RMN (d6-DMSO, δ): 9,8 (1H, s), 8,96 (1H, s), 8,62 (1H, s), 8,12 (1H, d, J= 8,7 Hz), 8,02 (1H, d, J= 2,7 Hz), 7,70 (1H, dd, J= 8,7 Hz, J= 2,7 Hz), 7,56 (1H, d, J= 8,7 Hz), 7,04 (1H, d, J= 8,7 Hz), 1,25-1,40 (3H, m), 1,11 (18H, d, J= 7,2 Hz).
(Etapa 3) Síntese de éster metílico do ácido 4-(3-cloro-4- triisopropilsililoxifenilamino)-quinazolina-6-carboxílico (X-2)
[0229] De 4-(3-cloro-4-triisopropilsililoxifenilamino)-6- iodoquinazolina (III-5, 21,8 g), éster metílico do ácido 4-(3-cloro-4- triisopropilsililoxifenilamino)-quinazolina-6-carboxílico (X-2, 20,4 g) foi obtido como um sólido amarelo da mesma maneira que para a primeira etapa do Exemplo de referência 1. 1H RMN (d6-DMSO, δ): 10,2 (1H, s), 9,26 (1H, s), 8,66 (1H, s), 8,30 (1H, d, J= 8,7 Hz), 8,01 (1H, d, J= 2,4 Hz), 7,84 (1H, d, J= 8,7 Hz), 7,71 (1H, dd, J= 9 Hz, J= 2,1 Hz), 7,04 (1H, d, J= 8,7 Hz), 3,96 (3H, s), 1,29-1,41 (3H, m), 1,11 (18H, d, J= 7,2 Hz).
(Etapa 4) Síntese de metoximetilamida de ácido 4-(3-cloro-4- triisopropilsililoxifenilamino)-quinazolina-6-carboxílico (XI-4)
[0230] De éster metílico do ácido 4-(3-cloro-4- triisopropilsililoxifenilamino)-quinazolina-6-carboxílico (X-2, 10 g), metoximetilamida de ácido 4-(3-cloro-4-triisopropilsililoxifenilamino)- quinazolina-6-carboxílico (XI-4, 4,1 g) foi obtida como um sólido incolor da mesma maneira que para a segunda etapa do Exemplo de referência 1. 1H RMN (d6-DMSO, δ): 10,0 (1H, s), 8,80 (1H, s), 8,65 (1H, s), 7,97-8,08 (2H, m), 7,81 (1H, d, J= 8,7 Hz), 7,70-7,75 (1H, m), 7,04 (1H, d, J= 9,0 Hz), 3,58 (3H, s), 3,35 (3H, s), 1,29-1,41 (3H, m), 1,11 (18H, d, J= 7,5 Hz).
(Etapa 5) Síntese de 4-(3-cloro-4-triisopropilsililoxifenilamino)-6-(1-oxo- 2-butin-1-ila)quinazolina (VII-20)
[0231] De metoximetilamida de ácido 4-(3-cloro-4- triisopropilsililoxifenilamino)-quinazolina-6-carboxílico (XI-4, 4,1 g), 4-(3- cloro-4-triisopropilsililoxifenilamino)-6-(1-oxo-2-butin-1-ila)quinazolina (VII-20, 1,3 g) foi obtida como um óleo amarelo da mesma maneira que para a terceira etapa do Exemplo de referência 1. 1H RMN (d6-DMSO, δ): 10,3 (1H, s), 9,24 (1H, s), 8,67 (1H, s), 8,45 (1H, d, J= 8,7 Hz), 7,99 (1H, s), 7,88(1H, s, J= 8,7 Hz), 7,68 (1H, d, J= 9,0 Hz), 7,06 (1H, d, J= 9,0 Hz), 2,28 (3H, s), 1,29-1,41 (3H, m), 1,11 (18H, d, J= 6,9 Hz).
(Etapa 6) Síntese de 4-(3-cloro-4-triisopropilsililoxifenilamino)-6-(1-(2- (N-(ter-butoxicarbonila)-N-metilaminoetoxiimino)-2-butin-1- ila)quinazolina (VIII-201)
[0232] De 4-(3-cloro-4-triisopropilsililoxifenilamino)-6-(1-oxo-2- butin-1-ila)quinazolina (VII-20, 1,3 g), 4-(3-cloro-4- triisopropilsililoxifenilamino)-6-(1-(2-(N-(ter-butoxicarbonila)-N- metilaminoetoxiimino)-2-butin-1-ila)quinazolina (VIII-201, 1,1 g) foi obtida como um sólido amarelo da mesma maneira que para a segunda etapa do Exemplo 2. ESI-MS (M/Z): (M+) = 666,71, (M+H) = 667,73
(Etapa 7) Síntese de 4-(3-cloro-4-hidroxifenilamino)-6-(1-(2-(N-(terc- butoxicarbonila)-N-metilaminoetoxiimino)-2-butin-1-ila)quinazolina (VIII202)
[0233] 4-(3-Cloro-4-triisopropilsililoxifenilamino)-6-(1-(2-(N-(terc- butoxicarbonila)-N-metilaminoetoxiimino)-2-butin-1-ila)quinazolina (VIII-201, 1,1 g) foi dissolvida em 20 ml de tetrahidrofurano, e 6,7 ml de solução de fluoreto de tetrabutilamônio a 1 mol/l em tetrahidrofurano foram adicionados, seguidos de agitação à temperatura ambiente por 30 minutos. Depois de completada a reação, 10 ml de água e 10 ml de acetato de etila foram adicionados para separar as camadas. A camada aquosa foi novamente extraída com 10 ml de acetato de etila duas vezes, e todas as camadas orgânicas foram combinadas, lavadas com água e solução aquosa saturada de cloreto de sódio, e secadas em sulfato de magnésio anidro. O filtrado foi concentrado, e o resíduo foi lavado com hexano-acetato de etila (1:1) para obter 4-(3-cloro-4- hidroxifenilamino)-6-(1-(2-(N-(ter-butoxicarbonila)-N- metilaminoetoxiimino)-2-butin-1-ila)quinazolina (VIII-202, 0,7 g) como um sólido amarelo. 1H RMN (d6-DMSO, δ): 9,96 (1H, s), 8,73 (1H, s), 8,55 (1H, s), 8,21 (1H, d, J= 8,7 Hz), 7,75-7,86 (2H, m), 7,50 (1H, d, J= 7,8 Hz), 7,00 (1H, d, J= 8,7 Hz), 4,36 (2H, bs), 3,56 (2H, bs), 2,86 (3H, bs), 2,25 (3H, bs), 1,36 (9H, s).
(Etapa 8) Síntese de 4-(3-cloro-4-(piridin-3-ilmetoxi)fenilamino)-6-(1-(2- (N-(terc-butoxicarbonila)-N-metilaminoetoxiimino)-2-butin-1- ila)quinazolina (VIII-203)
[0234] 4-(3-Cloro-4-hidroxifenilamino)-6-(1-(2-(N-(terc- butoxicarbonila)-N-metilaminoetoxiimino)-2-butin-1-ila)quinazolina (VIII-202, 70 mg), 87 mg de bromidrato de 3-bromometilpiridina, e 223 mg de carbonato de césio foram dissolvidos em 1,1 ml de N, N- dimetilformamida-água (10,1), seguidos de agitação à temperatura ambiente por 3 horas. Depois de completada a reação, 5 ml de água e 5 ml de acetato de etila foram adicionados para separar as camadas. A camada aquosa foi novamente extraída com 5 ml de acetato de etila duas vezes, e todas as camadas orgânicas foram combinadas, lavadas com água e solução aquosa saturada de cloreto de sódio nesta ordem, e secadas em sulfato de magnésio anidro. O filtrado foi concentrado, e o resíduo foi purificado por cromatografia de coluna sobre sílica-gel (eluindo com hexano: acetato de etila = 1:1) para obter 4-(3-cloro-4- (piridin-3-ilmetoxi)fenilamino)-6-(1-(2-(N-(terc-butoxicarbonila)-N- metilaminoetoxiimino)-2-butin-1-ila)quinazolina (VIII-203, 70 mg) como um óleo amarelo. 1H RMN (d6-DMSO, δ): 10,0 (1H, bs), 8,74 (1H, bs), 8,72 (1H, bs), 8,60 (1H, s), 8,57 (1H, d, J= 4,4 Hz), 8,23 (1H, d, J= 8,8 Hz), 7,97 (1H, bs), 7,91 (1H, d, J= 8,0 Hz), 7,80 (1H, d, J= 8,8 Hz), 7,72 (1H, d, J= 8,8 Hz), 7,46 (1H, dd, J= 7,6 Hz, J= 4,4 Hz), 7,33 (1H, d, J= 8,8 Hz), 5,29 (2H, s), 4,37 (2H, bs), 3,56 (2H, bs), 2,86 (3H, bs), 2,25 (3H, bs), 1,36 (9H, s).
(Etapa 9) Síntese de 4-(3-cloro-4-(piridin-3-ilmetoxi)fenilamino)-6-(1-(2- N-metilaminoetoxiimino)-2-butin-1-ila)quinazolina (VIII-204)
[0235] Partindo de 4-(3-cloro-4-(piridin-3-ilmetoxi)fenilamino)-6-(1- (2-(N-(terc-butoxicarbonila)-N-metilaminoetoxiimino)-2-butin-1- ila)quinazolina (VIII-203, 70 mg), e da mesma maneira que para a segunda etapa do Exemplo 2, a reação foi realizada, e purificação foi efetuada por recristalização de hexano-acetato de etila para obter 4-(3- cloro-4-(piridin-3-ilmetoxi)fenilamino)-6-(1-(2-N-metilaminoetoxiimino)- 2-butin-1-ila)quinazolina (VIII-204, 7 mg) como um sólido amarelo. 10,3 (1H, s), 8,84 (1H, s), 8,72 (1H, s), 8,42-8,65 (2H, m), 8,26 (1H, d, J= 7,6 Hz), 7,98 (1H, s), 7,91 (1H, brs), 7,81 (1H, brs), 7,71 (1H, brs), 7,47 (1H, brs), 7,34 (1H, d, J= 8,0 Hz), 5,30 (2H, s), 4,53 (2H, brs), 3,38 (2H, brs), 2,68 (3H, s), 2,26 (3H, s).
[0236] Da mesma maneira que para os exemplos 7 a 10, foi sintetizado o seguinte composto. Fórmula química 81
Figure img0130
Tabela 15
Figure img0131
Figure img0132
Figure img0133
Figure img0134
Tabela 16
Figure img0135
Figure img0136
Figure img0137
Figure img0138
Tabela 17
Figure img0139
Figure img0140
Figure img0141
Figure img0142
Tabela 18
Figure img0143
Figure img0144
Figure img0145
Tabela 19
Figure img0146
Figure img0147
Figure img0148
Tabela 20
Figure img0149
Figure img0150
Figure img0151
Figure img0152
Tabela 21
Figure img0153
Figure img0154
Figure img0155
Figure img0156
Tabela 22
Figure img0157
Figure img0158
Figure img0159
Figure img0160
Tabela 23
Figure img0161
Figure img0162
Figure img0163
Figure img0164
Tabela 24
Figure img0165
Figure img0166
Figure img0167
Figure img0168
Figure img0169
Tabela 25
Figure img0170
Figure img0171
Figure img0172
Figure img0173
Tabela 26
Figure img0174
Figure img0175
Figure img0176
Tabela 27
Figure img0177
Figure img0178
Figure img0179
Figure img0180
Tabela 28
Figure img0181
Figure img0182
Figure img0183
Figure img0184
Tabela 29
Figure img0185
Figure img0186
Figure img0187
Figure img0188
Tabela 30
Figure img0189
Figure img0190
Figure img0191
Tabela 31
Figure img0192
Figure img0193
Figure img0194
Fórmula química 82
Figure img0195
Tabela 32
Figure img0196
Figure img0197
Figure img0198
Figure img0199
Tabela 33
Figure img0200
Figure img0201
Figure img0202
Figure img0203
Tabela 34
Figure img0204
Figure img0205
Figure img0206
Figure img0207
Tabela 35
Figure img0208
Figure img0209
Figure img0210
Figure img0211
Tabela 36
Figure img0212
Figure img0213
Figure img0214
Figure img0215
Tabela 37
Figure img0216
Figure img0217
Figure img0218
Figure img0219
Tabela 38
Figure img0220
Figure img0221
Figure img0222
Tabela 39
Figure img0223
Figure img0224
Figure img0225
Figure img0226
Tabela 40
Figure img0227
Figure img0228
Figure img0229
Figure img0230
Tabela 41
Figure img0231
Figure img0232
Figure img0233
Figure img0234
Tabela 42
Figure img0235
Figure img0236
Figure img0237
Tabela 43
Figure img0238
Figure img0239
Figure img0240
Tabela 44
Figure img0241
Figure img0242
Figure img0243
Tabela 45
Figure img0244
Figure img0245
(onde um átomo assinado com * é um átomo de carbono assimétrico) Tabela 46
Figure img0246
Figure img0247
Figure img0248
Figure img0249
Figure img0250
(Etapa 1) Síntese de 4-(3-cloro-4-(3-fluorbenziloxi)fenilamino)-6- (carboximetoxiimino)-2-butin-1-ila)quinazolina (VIII-38)
[0237] 4-(3-Cloro-4-(3-fluorbenziloxi)fenilamino)-6- (metoxicarbonilmetoxiimino)-2-butin-1-ila)quinazolina (VIII-43, 1,2 g) foi dissolvida em uma mistura de 12 ml de tetrahidrofurano e 12 ml de metanol, e 1,5 ml de solução aquosa de hidróxido de sódio a 2 mol/l foi adicionado, seguido de agitação à temperatura ambiente por 1,5 hora. A mistura reacional foi diluída com 20 ml de acetato de etila, 1,6 ml de ácido clorídrico a 2 mol/l foi adicionado, e água foi adicionada, dessa forma, uma substância desejada foi precipitada. Um precipitado foi recolhido por filtração, lavado com água e acetato de etila, e secado para obter 4-(3- cloro-4-(3-fluorbenziloxi)fenilamino)-6-(carboximetoxiimino)-2-butin-1- ila)quinazolina (VIII-38, 0,9 g) como um sólido amarelo. 1H RMN (d6-DMSO, δ): 10,18 (1H, brs), 8,77 (1H, s), 8,60 (1H, s), 8,19 (1H, dd, J= 2,0, 11,6 Hz), 7,95 (1H, d, J= 3,2 Hz), 7,80 (1H, d, J= 11,6 Hz), 7,67 (1H, dd, J= 3,2, 11,6 Hz), 7,51-7,44 (1H, m), 7,35-7,26 (3H, m), 7,22-7,15 (1H, m), 5,27 (2H, s), 4,83 (2H, s), 2,27 (3H, s).
(Etapa 2) Síntese de 4-(3-cloro-4-(3-fluorbenziloxi)fenilamino)-6-((2- dimetilaminoetilcarbamoila)metoxiimino)-2-butin-1-ila)quinazolina (VIII-39)
[0238] 4-(3-Cloro-4-(3-fluorbenziloxi)fenilamino)-6- (carboximetoxiimino)-2-butin-1-ila)quinazolina (VIII-38, 70 mg), 24 mg de 1-hidroxibenzotriazol, e 27 mg de cloridrato de 1-etila 3-(3- dimetilaminopropila)carbodiimida foram dissolvidos em 1,4 ml de N,N- dimetilformamida, a mistura foi agitada à temperatura ambiente por 5 minutos, e 22 μl de N,N-dimetiletilenodiamina foram adicionados, seguidos de agitação à temperatura ambiente por 2 horas. Depois de completada a reação, a mistura reacional foi diluída com acetato de etila, e água e solução aquosa saturada de bicarbonato de sódio foram adicionadas para separar as camadas. A camada orgânica foi lavada com água, e secada em sulfato de sódio, e o filtrado foi concentrado. Acetato de etila foi adicionado ao resíduo concentrado para solidificar o material, e o sólido foi recolhido por filtração, e secado obter 4-(3-cloro- 4-(3-fluorbenziloxi)fenilamino)-6-((2- dimetilaminoetilcarbamoila)metoxiimino)-2-butin-1-ila)quinazolina (VIII39, 30 mg) como um cristal incolor. 1H RMN (d6-DMSO, δ): 10,12 (1H, s), 8,77 (1H, s), 8,59 (1H, s), 8,19 (1H, dd, J= 2,0, 12,0 Hz), 8,08 (1H, brs), 7,95 (1H, d, J= 3,2 Hz), 7,80 (1H, d, J= 11,6 Hz), 7,70-7,62 (2H, m), 7,51-7,44 (1H, m), 7,34-7,26 (3H, m), 7,21-7,15 (1H, s), 5,27 (2H, s), 4,69 (2H, s), 3,22 (2H, dd, J= 8,4, 16,0 Hz) 2,31 (1H, t, J= 8,4 Hz), 2,28 (3H, s), 2,11 (6H, s).
[0239] Da mesma maneira que para o exemplo 11, foi sintetizado o seguinte composto. Tabela 47
Figure img0251
Figure img0252
Figure img0253
Figure img0254
(Etapa 1) Síntese de 4-(3-cloro-4-(3-fluorbenziloxi)fenilamino)-6- (pirrolidin-l-iliminometila)quinazolina (IX-1)
[0240] Em uma mistura de 1 ml de tetrahidrofurano e 0,1 ml de água foram dissolvidos 40 mg de 4-(3-cloro-4-(3-fluorbenziloxi)fenilamino)-6- formilquinazolina (IV-1) e 13 mg de cloridrato de 1-amino-pirrolidina, seguido de uma reação à temperatura ambiente por uma noite. Depois da reação, solução saturada aquosa de bicarbonato de sódio foi adicionada, seguida de extração com acetato de etila. A camada orgânica foi desidratada sendo passada por Presep (marca registrada), e o filtrado foi concentrado. O resíduo concentrado foi purificado por cromatografia (eluindo com hexano: acetato de etila = 2:1 ^ 1:1) usando uma coluna de amina para obter 38 mg de 4-(3-cloro-4-(3- fluorbenziloxi)fenilamino)-6-(pirrolidin-1-iliminometila)quinazolina (IX-1) como um sólido amarelo. 1H RMN (d6-DMSO, δ): 9,76 (1H, s), 8,52 (1H, s), 8,40 (1H, brs), 8,08 (1H, d, J= 6,6 Hz), 8,06 (1H, d, J= 1,8 Hz), 7,76 (1H, dd, J= 6,6 Hz, J= 1,8 Hz), 7,69 (1H, dd, J= 6,6 Hz), 7,50-7,45 (1H, m), 7,357,26 (3H, m), 7,19 (1H, t, J= 6,6 Hz), 5,26 (2H, s), 3,39 (4H, br), 1,94 (4H, br)
[0241] Da mesma maneira que para o exemplo 12, foi sintetizado o seguinte composto.
Figure img0255
Tabela 48
Figure img0256
Figure img0257
Figure img0258
Tabela 49
Figure img0259
Figure img0260
Figure img0261
[0242] Da mesma maneira que para o exemplo acima, é possível sintetizar o seguinte composto. Isto é, no composto representado pela fórmula geral (A) a seguir:
Figure img0262
os seguintes compostos representados por uma combinação de um grupo no qual RAé um grupo selecionado de a1 a a90:
Figure img0263
Figure img0264
Figure img0265
onde Me é metila, um grupo no qual RBé selecionado de b1 a b6 a seguir:
Figure img0266
onde Me é metila, um grupo no qual RCé selecionado de c1 a c3 a seguir:
Figure img0267
um grupo no qual RDé selecionado de d1 a d22 a seguir:
Figure img0268
onde Me é metila podem ser sintetizados. (a1, b1, c1, d1), (a1, b1, c1, d2), (a1, b1, c1, d3), (a1, b1, c1, d4), (a1, b1, c1, d5), (a1, b1, c1, d6), (a1, b1, c1, d7), (a1, b1, c1, d8), (a1, b1, c1, d9), (a1, b1, c1, d10), (a1, b1, c1, d11), (a1, b1, c1, d12), (a1, b1, c1, d13), (a1, b1, c1, d14), (a1, b1, c1, d15), (a1, b1, c1, d16), (a1, b1, c1, d17), (a1, b1, c1, d18), (a1, b1, c1, d19), (a1, b1, c1, d20), (a1, b1, c1, d21), (a1, b1, c1, d22), (a1, b1, c2, d1), (a1, b1, c2, d2), (a1, b1, c2, d3), (a1, b1, c2, d4), (a1, b1, c2, d5), (a1, b1, c2, d6), (a1, b1, c2, d7), (a1, b1, c2, d8), (a1, b1, c2, d9), (a1, b1, c2, d10), (a1, b1, c2, d11), (a1, b1, c2, d12), (a1, b1, c2, d13), (a1, b1, c2, d14), (a1, b1, c2, d15), (a1, b1, c2, d16), (a1, b1, c2, d17), (a1, b1, c2, d18), (a1, b1, c2, d19), (a1, b1, c2, d20), (a1, b1, c2, d21), (a1, b1, c2, d22), (a1, b1, c3, d1), (a1, b1, c3, d2), (a1, b1, c3, d3), (a1, b1, c3, d4), (a1, b1, c3, d5), (a1, b1, c3, d6), (a1, b1, c3, d7), (a1, b1, c3, d8), (a1, b1, c3, d9), (a1, b1, c3, d10), (a1, b1, c3, d11), (a1, b1, c3, d12), (a1, b1, c3, d13), (a1, b1, c3, d14), (a1, b1, c3, d15), (a1, b1, c3, d16), (a1, b1, c3, d17), (a1, b1, c3, d18), (a1, b1, c3, d19), (a1, b1, c3, d20), (a1, b1, c3, d21), (a1, b1, c3, d22), (a1, b2, c1, d1), (a1, b2, c1, d2), (a1, b2, c1, d3), (a1, b2, c1, d4), (a1, b2, c1, d5), (a1, b2, c1, d6), (a1, b2, c1, d7), (a1, b2, c1, d8), (a1, b2, c1, d9), (a1, b2, c1, d10), (a1, b2, c1, d11), (a1, b2, c1, d12), (a1, b2, c1, d13), (a1, b2, c1, d14), (a1, b2, c1, d15), (a1, b2, c1, d16), (a1, b2, c1, d17), (a1, b2, c1, d18), (a1, b2, c1, d19), (a1, b2, c1, d20), (a1, b2, c1, d21), (a1, b2, c1, d22), (a1, b2, c2, d1), (a1, b2, c2, d2), (a1, b2, c2, d3), (a1, b2, c2, d4), (a1, b2, c2, d5), (a1, b2, c2, d6), (a1, b2, c2, d7), (a1, b2, c2, d8), (a1, b2, c2, d9), (a1, b2, c2, d10), (a1, b2, c2, d11), (a1, b2, c2, d12), (a1, b2, c2, d13), (a1, b2, c2, d14), (a1, b2, c2, d15), (a1, b2, c2, d16), (a1, b2, c2, d17), (a1, b2, c2, d18), (a1, b2, c2, d19), (a1, b2, c2, d20), (a1, b2, c2, d21), (a1, b2, c2, d22), (a1, b2, c3, d1), (a1, b2, c3, d2), (a1, b2, c3, d3), (a1, b2, c3, d4), (a1, b2, c3, d5), (a1, b2, c3, d6), (a1, b2, c3, d7), (a1, b2, c3, d8), (a1, b2, c3, d9), (a1, b2, c3, d10), (a1, b2, c3, d11), (a1, b2, c3, d12), (a1, b2, c3, d13), (a1, b2, c3, d14), (a1, b2, c3, d15), (a1, b2, c3, d16), (a1, b2, c3, d17), (a1, b2, c3, d18), (a1, b2, c3, d19), (a1, b2, c3, d20), (a1, b2, c3, d21), (a1, b2, c3, d22), (a1, b3, c1, d1), (a1, b3, c1, d2), (a1, b3, c1, d3), (a1, b3, c1, d4), (a1, b3, c1, d5), (a1, b3, c1, d6), (a1, b3, c1, d7), (a1, b3, c1, d8), (a1, b3, c1, d9), (a1, b3, c1, d10), (a1, b3, c1, d11), (a1, b3, c1, d12), (a1, b3, c1, d13), (a1, b3, c1, d14), (a1, b3, c1, d15), (a1, b3, c1, d16), (a1, b3, c1, d17), (a1, b3, c1, d18), (a1, b3, c1, d19), (a1, b3, c1, d20), (a1, b3, c1, d21), (a1, b3, c1, d22), (a1, b3, c2, d1), (a1, b3, c2, d2), (a1, b3, c2, d3), (a1, b3, c2, d4), (a1, b3, c2, d5), (a1, b3, c2, d6), (a1, b3, c2, d7), (a1, b3, c2, d8), (a1, b3, c2, d9), (a1, b3, c2, d10), (a1, b3, c2, d11), (a1, b3, c2, d12), (a1, b3, c2, d13), (a1, b3, c2, d14), (a1, b3, c2, d15), (a1, b3, c2, d16), (a1, b3, c2, d17), (a1, b3, c2, d18), (a1, b3, c2, d19), (a1, b3, c2, d20), (a1, b3, c2, d21), (a1, b3, c2, d22), (a1, b3, c3, d1), (a1, b3, c3, d2), (a1, b3, c3, d3), (a1, b3, c3, d4), (a1, b3, c3, d5), (a1, b3, c3, d6), (a1, b3, c3, d7), (a1, b3, c3, d8), (a1, b3, c3, d9), (a1, b3, c3, d10), (a1, b3, c3, d11), (a1, b3, c3, d12), (a1, b3, c3, d13), (a1, b3, c3, d14), (a1, b3, c3, d15), (a1, b3, c3, d16), (a1, b3, c3, d17), (a1, b3, c3, d18), (a1, b3, c3, d19), (a1, b3, c3, d20), (a1, b3, c3, d21), (a1, b3, c3, d22), (a1, b4, c1, d1), (a1, b4, c1, d2), (a1, b4, c1, d3), (a1, b4, c1, d4), (a1, b4, c1, d5), (a1, b4, c1, d6), (a1, b4, c1, d7), (a1, b4, c1, d8), (a1, b4, c1, d9), (a1, b4, c1, d10), (a1, b4, c1, d11), (a1, b4, c1, d12), (a1, b4, c1, d13), (a1, b4, c1, d14), (a1, b4, c1, d15), (a1, b4, c1, d16), (a1, b4, c1, d17), (a1, b4, c1, d18), (a1, b4, c1, d19), (a1, b4, c1, d20), (a1, b4, c1, d21), (a1, b4, c1, d22), (a1, b4, c2, d1), (a1, b4, c2, d2), (a1, b4, c2, d3), (a1, b4, c2, d4), (a1, b4, c2, d5), (a1, b4, c2, d6), (a1, b4, c2, d7), (a1, b4, c2, d8), (a1, b4, c2, d9), (a1, b4, c2, d10), (a1, b4, c2, d11), (a1, b4, c2, d12), (a1, b4, c2, d13), (a1, b4, c2, d14), (a1, b4, c2, d15), (a1, b4, c2, d16), (a1, b4, c2, d17), (a1, b4, c2, d18), (a1, b4, c2, d19), (a1, b4, c2, d20), (a1, b4, c2, d21), (a1, b4, c2, d22), (a1, b4, c3, d1), (a1, b4, c3, d2), (a1, b4, c3, d3), (a1, b4, c3, d4), (a1, b4, c3, d5), (a1, b4, c3, d6), (a1, b4, c3, d7), (a1, b4, c3, d8), (a1, b4, c3, d9), (a1, b4, c3, d10), (a1, b4, c3, d11), (a1, b4, c3, d12), (a1, b4, c3, d13), (a1, b4, c3, d14), (a1, b4, c3, d15), (a1, b4, c3, d16), (a1, b4, c3, d17), (a1, b4, c3, d18), (a1, b4, c3, d19), (a1, b4, c3, d20), (a1, b4, c3, d21), (a1, b4, c3, d22), (a1, b5, c1, d1), (a1, b5, c1, d2), (a1, b5, c1, d3), (a1, b5, c1, d4), (a1, b5, c1, d5), (a1, b5, c1, d6), (a1, b5, c1, d7), (a1, b5, c1, d8), (a1, b5, c1, d9), (a1, b5, c1, d10), (a1, b5, c1, d11), (a1, b5, c1, d12), (a1, b5, c1, d13), (a1, b5, c1, d14), (a1, b5, c1, d15), (a1, b5, c1, d16), (a1, b5, c1, d17), (a1, b5, c1, d18), (a1, b5, c1, d19), (a1, b5, c1, d20), (a1, b5, c1, d21), (a1, b5, c1, d22), (a1, b5, c2, d1), (a1, b5, c2, d2), (a1, b5, c2, d3), (a1, b5, c2, d4), (a1, b5, c2, d5), (a1, b5, c2, d6), (a1, b5, c2, d7), (a1, b5, c2, d8), (a1, b5, c2, d9), (a1, b5, c2, d10), (a1, b5, c2, d11), (a1, b5, c2, d12), (a1, b5, c2, d13), (a1, b5, c2, d14), (a1, b5, c2, d15), (a1, b5, c2, d16), (a1, b5, c2, d17), (a1, b5, c2, d18), (a1, b5, c2, d19), (a1, b5, c2, d20), (a1, b5, c2, d21), (a1, b5, c2, d22), (a1, b5, c3, d1), (a1, b5, c3, d2), (a1, b5, c3, d3), (a1, b5, c3, d4), (a1, b5, c3, d5), (a1, b5, c3, d6), (a1, b5, c3, d7), (a1, b5, c3, d8), (a1, b5, c3, d9), (a1, b5, c3, d10), (a1, b5, c3, d11), (a1, b5, c3, d12), (a1, b5, c3, d13), (a1, b5, c3, d14), (a1, b5, c3, d15), (a1, b5, c3, d16), (a1, b5, c3, d17), (a1, b5, c3, d18), (a1, b5, c3, d19), (a1, b5, c3, d20), (a1, b5, c3, d21), (a1, b5, c3, d22), (a1, b6, c1, d1), (a1, b6, c1, d2), (a1, b6, c1, d3), (a1, b6, c1, d4), (a1, b6, c1, d5), (a1, b6, c1, d6), (a1, b6, c1, d7), (a1, b6, c1, d8), (a1, b6, c1, d9), (a1, b6, c1, d10), (a1, b6, c1, d11), (a1, b6, c1, d12), (a1, b6, c1, d13), (a1, b6, c1, d14), (a1, b6, c1, d15), (a1, b6, c1, d16), (a1, b6, c1, d17), (a1, b6, c1, d18), (a1, b6, c1, d19), (a1, b6, c1, d20), (a1, b6, c1, d21), (a1, b6, c1, d22), (a1, b6, c2, d1), (a1, b6, c2, d2), (a1, b6, c2, d3), (a1, b6, c2, d4), (a1, b6, c2, d5), (a1, b6, c2, d6), (a1, b6, c2, d7), (a1, b6, c2, d8), (a1, b6, c2, d9), (a1, b6, c2, d10), (a1, b6, c2, d11), (a1, b6, c2, d12), (a1, b6, c2, d13), (a1, b6, c2, d14), (a1, b6, c2, d15), (a1, b6, c2, d16), (a1, b6, c2, d17), (a1, b6, c2, d18), (a1, b6, c2, d19), (a1, b6, c2, d20), (a1, b6, c2, d21), (a1, b6, c2, d22), (a1, b6, c3, d1), (a1, b6, c3, d2), 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‘(gLP ‘εo >q ‘θe) ‘(^up ‘εo >q ‘ge) ‘(gup ‘go >q ‘ge) ‘(sup ‘go (a6, b6, c3, d5), (a6, b6, c3, d6), (a6, b6, c3, d7), (a6, b6, c3, d8), (a6, b6, c3, d9), (a6, b6, c3, d10), (a6, b6, c3, d11), (a6, b6, c3, d12), (a6, b6, c3, d13), (a6, b6, c3, d14), (a6, b6, c3, d15), (a6, b6, c3, d16), (a6, b6, c3, d17), (a6, b6, c3, d18), (a6, b6, c3, d19), (a6, b6, c3, d20), (a6, b6, c3, d21), (a6, b6, c3, d22), (a7, b1, c1, d1), (a7, b1, c1, d2), (a7, b1, c1, d3), (a7, b1, c1, d4), (a7, b1, c1, d5), (a7, b1, c1, d6), (a7, b1, c1, d7), (a7, b1, c1, d8), (a7, b1, c1, d9), (a7, b1, c1, d10), (a7, b1, c1, d11), (a7, b1, c1, d12), (a7, b1, c1, d13), (a7, b1, c1, d14), (a7, b1, c1, d15), (a7, b1, c1, d16), (a7, b1, c1, d17), (a7, b1, c1, d18), (a7, b1, c1, d19), (a7, b1, c1, d20), (a7, b1, c1, d21), (a7, b1, c1, d22), (a7, b1, c2, d1), (a7, b1, c2, d2), (a7, b1, c2, d3), (a7, b1, c2, d4), (a7, b1, c2, d5), (a7, b1, c2, d6), (a7, b1, c2, d7), (a7, b1, c2, d8), (a7, b1, c2, d9), (a7, b1, c2, d10), (a7, b1, c2, d11), (a7, b1, c2, d12), (a7, b1, c2, d13), (a7, b1, c2, d14), (a7, b1, c2, d15), (a7, b1, c2, d16), (a7, b1, c2, d17), (a7, b1, c2, d18), (a7, b1, c2, d19), (a7, b1, c2, d20), (a7, b1, c2, d21), (a7, b1, c2, d22), (a7, b1, c3, d1), (a7, b1, c3, d2), (a7, b1, c3, d3), (a7, b1, c3, d4), (a7, b1, c3, d5), (a7, b1, c3, d6), (a7, b1, c3, d7), (a7, b1, c3, d8), (a7, b1, c3, d9), (a7, b1, c3, d10), (a7, b1, c3, d11), (a7, b1, c3, d12), (a7, b1, c3, d13), (a7, b1, c3, d14), (a7, b1, c3, d15), (a7, b1, c3, d16), (a7, b1, c3, d17), (a7, b1, c3, d18), (a7, b1, c3, d19), (a7, b1, c3, d20), (a7, b1, c3, d21), (a7, b1, c3, d22), (a7, b2, c1, d1), (a7, b2, c1, d2), (a7, b2, c1, d3), (a7, b2, c1, d4), (a7, b2, c1, d5), (a7, b2, c1, d6), (a7, b2, c1, d7), (a7, b2, c1, d8), (a7, b2, c1, d9), (a7, b2, c1, d10), (a7, b2, c1, d11), (a7, b2, c1, d12), (a7, b2, c1, d13), (a7, b2, c1, d14), (a7, b2, c1, d15), (a7, b2, c1, d16), (a7, b2, c1, d17), (a7, b2, c1, d18), (a7, b2, c1, d19), (a7, b2, c1, d20), (a7, b2, c1, d21), (a7, b2, c1, d22), (a7, b2, c2, d1), (a7, b2, c2, d2), (a7, b2, c2, d3), (a7, b2, c2, d4), (a7, b2, c2, d5), (a7, b2, c2, d6), (a7, b2, c2, d7), (a7, b2, c2, d8), (a7, b2, c2, d9), (a7, b2, c2, d10), (a7, b2, c2, d11), (a7, b2, c2, d12), (a7, b2, c2, d13), (a7, b2, c2, d14), (a7, b2, c2, d15), (a7, b2, c2, d16), (a7, b2, c2, d17), (a7, b2, c2, d18), (a7, ‘Ze) ‘(LLP ‘SO>q ‘ze) ‘(θkP ‘zo >q ‘ze) *(6P ‘zo >q ‘Zθ) ‘(8P ‘zo >q ‘Zθ) ‘(ZP ‘30 >q 7e) ‘(9P ‘ZO >q 7e) ‘(gp ‘so >q ‘ze) ‘(^p ‘so >q 7e) ‘(εp ‘SO >q ‘ze) ‘(SP ‘30 >q ‘ze) ‘(LP ‘ZO >q ‘ze) ‘(SZP ‘ LO >q ‘ze) ‘(LZP ‘LO >q ‘ze) ‘(OZP ‘ LO >q ‘ze) ‘(6kP ‘ LO >q ‘ze) ‘(gLP ‘LO >q ‘ze) ‘(ZLP ‘LO >q ‘ze) ‘(9LP ‘LO >q ‘ze) ‘(gLP ‘LO >q ‘ze) ‘(^LP ‘LO >q ‘ze) ‘(εLP ‘LO >q ‘ze) ‘(ZLP ‘LO >q ‘ze) ‘(LLP ‘LO >q ‘ze) ‘(OLP ‘LO >q ‘ze) ‘(6P ‘LO >q ‘ZB) ‘(gp ‘LO>q ‘ZB) ‘(ZP ‘LO>q ‘ze) ‘(9P ‘LO >q ‘ze) ‘(gp ‘LO>q ‘ze) ‘(17P ‘LO>q ‘ZB) ‘(εp ‘LO >q ‘ze) ‘(SP ‘LO >q ‘ze) ‘(LP ‘LO >q ‘ze) ‘(SZP ‘εo ‘εq ‘ze) ‘(LZP ‘εo ‘εq ‘ze) ‘(OZP ‘εo ‘εq ‘ze) ‘(OLP ‘εo ‘εq ‘ze) ‘(gLP ‘εo ‘εq ‘ze) ‘(ZLP ‘εo ‘εq ‘ze) ‘(ΘLP ‘εo ‘εq ‘ze) ‘(gLP ‘εo ‘εq ‘ze) ‘(np ‘εo ‘εq ‘ze) ‘(εLP ‘εo ‘εq ‘ze) ‘(SLP ‘εo ‘εq ‘ze) ‘(LLP ‘εo ‘εq ‘ze) ‘(OLP ‘εo ‘εq ‘ze) ‘(6P ‘εo ‘εq ‘ze) ‘(gp ‘εo ‘εq ‘ze) ‘(ZP ‘εo ‘εq ‘ze) ‘(ΘP ‘εo ‘εq ‘ze) ‘(gp ‘εo ‘εq ‘ze) ‘(^p ‘εo ‘εq ‘ze) ‘(εp ‘εo ‘εq ‘ze) ‘(SP ‘εo ‘εq ‘ze) ‘(LP ‘εo ‘εq ‘ze) ‘(SZP ‘ZO ‘εq ‘ze) ‘(LZP ‘ZO ‘εq ‘ze) ‘(OZP ‘ZO ‘εq ‘ze) ‘(6LP ‘ZO ‘εq ‘ze) ‘(gLP ‘zo ‘εq ‘ze) ‘(ZLP ‘zo ‘εq ‘ze) ‘(9LP ‘zo ‘εq ‘ze) ‘(SLP ‘zo ‘εq ‘ze) ‘(np ‘zo ‘εq ‘ze) ‘(εLP ‘zo ‘εq ‘ze) ‘(SLP ‘ZO ‘εq ‘ze) ‘(LLP ‘zo ‘εq ‘ze) ‘(OLP ‘zo ‘εq ‘ze) ‘(6P ‘zo ‘εq ‘ze) ‘(gp ‘so ‘εq ‘ze) ‘(zp ‘zo ‘εq ‘ze) ‘(9P ‘zo ‘εq ‘ze) ‘(gp ‘so ‘εq ‘ze) ‘(t-p ‘so ‘εq ‘ze) ‘(εp ‘zo ‘εq ‘ze) ‘(SP ‘zo ‘εq ‘ze) ‘(LP ‘zo ‘εq ‘ze) ‘(ZZP ‘LO ‘εq ‘ze) ‘(LZP ‘LO ‘εq ‘ze) ‘(OZP ‘LO ‘εq ‘ze) ‘(6LP ‘LO ‘εq ‘ze) ‘(gLP ‘LO ‘εq ‘ze) ‘(ZLP ‘LO ‘εq ‘ze) ‘(SLP ‘LO ‘εq ‘ze) ‘(gLP ‘LO ‘εq ‘ze) ‘(np ‘LO ‘εq ‘ze) ‘(εLP ‘LO ‘εq ‘ze) ‘(ZLP ‘LO ‘εq ‘ze) ‘(LLP ‘LO ‘εq ‘ze) ‘(OLP ‘LO ‘εq ‘ze) ‘(6P ‘LO ‘εq ‘ze) ‘(gp ‘ LO ‘εq ‘ze) ‘(ZP ‘ LO ‘εq ‘ze) ‘(ΘP ‘ LO ‘εq ‘ze) ‘(gp ‘ LO ‘εq ‘ze) ‘(^p ‘ LO ‘εq ‘ze) ‘(εp ‘LO ‘εq ‘ze) ‘(SP ‘LO ‘εq ‘ze) ‘(LP ‘LO ‘εq ‘ze) ‘(SZP ‘εo ‘sq ‘ze) ‘(LZP ‘εo ‘zq ‘ze) ‘(OZP ‘εo ‘zq ‘ze) ‘(OLP ‘εo ‘zq ‘ze) ‘(gLP ‘εo ‘zq ‘ze) ‘(ZLP ‘εo ‘zq ‘ze) ‘(9LP ‘εo ‘zq ‘ze) ‘(gLP ‘εo ‘zq ‘ze) ‘(^LP ‘εo ‘zq ‘ze) ‘(εLP ‘εo ‘zq ‘ze) ‘(SLP ‘εo ‘sq ‘ze) ‘(LLP ‘εo ‘sq ‘ze) ‘(OLP ‘εo ‘sq ‘ze) ‘(6P ‘εo ‘sq ‘ze) ‘(gp ‘εo ‘sq ‘ze) ‘(ZP ‘εo ‘sq ‘ze) ‘(ΘP ‘εo ‘sq ‘ze) ‘(gp ‘εo ‘sq ‘ze) ‘(i7P ‘εo ‘sq ‘ze) ‘(εp ‘εo ‘sq ‘ze) ‘(SP ‘εo ‘sq ‘ze) ‘(LP ‘εo ‘sq ‘ze) ‘(SZP ‘zo ‘zq ‘ze) ‘(LZP ‘ZO ‘zq ‘Ze) ‘(OZP ‘ZO ‘zq ‘Ze) ‘(6LP ‘ZO ‘zq ‘ZB) ‘(εp ‘30 ‘θq ‘Zθ) *(3P ‘θq ‘Zθ) ‘(kP ‘30 ‘θq ‘Zθ) ‘(33P ‘ Lo ‘θq ‘Zθ) ‘(kZP ‘ Lo ‘θq ‘Zθ) ‘(OZP ‘ Lo ‘θq ‘Zθ) ‘(6kP ‘ Lo ‘θq 7B) ‘(8kP ‘ Lo ‘θq 7B) ‘(ZLP ‘ Lo ‘θq ‘Zθ) ‘(9kP ‘ Lo ‘θq ‘Zθ) ‘(SLP ‘LO ‘θq 7B) ‘(^LP ‘Lo ‘gq ‘Zθ) ‘(CLP ‘Lo ‘θq ‘ZB) ‘(ZLP ‘LO ‘gq ‘ZB) ‘(LLP ‘LO ‘gq ‘ZB) ‘(OLP ‘LO ‘gq ‘ZB) ‘(6P ‘Lo ‘gq ‘ZB) ‘(gp ‘LO ‘gq ‘ZB) ‘(ZP ‘LO ‘gq ‘ZB) ‘(gp ‘LO ‘gq ‘ZB) ‘(gp ‘ Lo ‘gq ‘ZB) ‘(17P ‘LO ‘gq ‘ZB) ‘(gp ‘LO ‘gq ‘ZB) ‘(SP ‘LO ‘gq ‘ze) ‘(LP ‘Lo ‘gq ‘ZB) ‘(SSP ‘εo ‘gq ‘ZB) ‘(LSP ‘CO ‘gq ‘ZB) ‘(OZP ‘CO ‘gq ‘ZB) ‘(6LP ‘CO ‘gq ‘ZB) ‘(8LP ‘CO ‘gq ‘ZB) ‘(ZLP ‘εo ‘gq ‘ZB) ‘(gLP ‘εo ‘gq ‘ZB) ‘(ÇLP ‘εo ‘gq ‘ze) ‘(^kP ‘go ‘gq ‘ZB) ‘(gLP ‘go ‘gq ‘ZB) ‘(SLP ‘εo ‘gq ‘ZB) ‘(LLP ‘εo ‘gq ‘ZB) ‘(OLP ‘CO ‘gq ‘ZB) ‘(6P ‘CO ‘gq 7B) ‘(gp ‘go ‘gq ‘ze) ‘(ZP ‘CO ‘gq 7B) ‘(9P ‘co ‘gq ‘ZB) ‘(gp ‘go ‘gq ‘ze) ‘(frp ‘go ‘gq ‘ze) ‘(gp ‘go ‘gq ‘ze) ‘(sp ‘εo ‘gq ‘ZB) ‘(LP ‘εo ‘gq ‘ZB) ‘(SZP ‘ZO ‘gq ‘ZB) ‘(LZP ‘ZO ‘gq ‘ZB) ‘(OZP ‘ZO ‘sq ‘ZB) ‘(6LP ‘zo ‘sq ‘ZB) ‘(SLP ‘ZO ‘sq ‘ZB) ‘(ZLP ‘ZO ‘sq ‘ZB) ‘(ΘLP ‘ZO ‘sq ‘ZB) ‘(ÇLP ‘zo ‘gq ‘ZB) ‘(^LP ‘ZO ‘gq ‘ZB) ‘(gLP ‘zo ‘gq ‘ZB) ‘(SLP ‘ZO ‘sq ‘ZB) ‘(LLP ‘ZO ‘sq ‘ZB) ‘(OLP ‘ZO ‘sq ‘ZB) ‘(ΘP ‘ZO ‘sq ‘ZB) ‘(SP ‘SO ‘sq ‘ZB) ‘(ZP ‘SO ‘sq ‘ZB) ‘(9P ‘ZO ‘sq ‘ZB) ‘(gp ‘so ‘gq ‘ZB) ‘(^p ‘SO ‘gq ‘ZB) ‘(CP ‘ZO ‘gq ‘ZB) ‘(SP ‘ZO ‘gq ‘ZB) ‘(LP ‘ZO ‘gq ‘ZB) ‘(SZP ‘LO ‘gq ‘ZB) ‘(LSP ‘LO ‘gq ‘ZB) ‘(OZP ‘LO ‘gq ‘ZB) ‘(6LP ‘LO ‘gq ‘ZB) ‘(8LP ‘LO ‘gq ‘ZB) ‘(ZLP ‘LO ‘gq ‘ZB) ‘(9LP ‘LO ‘gq ‘ZB) ‘(gLP ‘LO ‘gq ‘ZB) ‘(^LP ‘LO ‘gq ‘ZB) ‘(gLP ‘LO ‘gq ‘ZB) ‘(SLP ‘LO ‘gq ‘ZB) ‘(LLP ‘LO ‘gq ‘ZB) ‘(OLP ‘LO ‘gq ‘ZB) ‘(6P ‘ LO ‘gq ‘ZB) ‘(gp ‘ LO ‘gq ‘ZB) ‘(ZP ‘ LO ‘gq ‘ZB) ‘(9P ‘ LO ‘gq ‘ZB) ‘(gp ‘ LO ‘gq ye) ‘(17P ‘LO ‘gq ‘ZB) ‘(gp ‘LO ‘gq ‘ZB) ‘(SP ‘LO ‘gq ‘ZB) ‘(LP ‘LO ‘gq ‘ZB) ‘(ZZP ‘CO >q ‘ZB) ‘(LSP ‘CO >q 7B) ‘(OZP ‘CO >q 7B) ‘(6LP ‘CO >q 7B) ‘(SLP ‘εo >q ‘ZB) ‘(ZLP ‘εo >q 7B) ‘(9LP ‘CO >q 7B) ‘(gLP ‘CO >q 7B) ‘(HP ‘εo >q ‘ZB) ‘(gLP ‘εo >q ‘ZB) ‘(SLP ‘εo >q ‘ZB) ‘(LLP ‘εo >q ‘ZB) ‘(OLP ‘εo >q ‘ZB) ‘(6P ‘CO >q 7B) ‘(gp ‘go >q ‘ZB) ‘(ZP ‘CO >q 7B) ‘(9P ‘εo >q ‘ZB) ‘(gp ‘go >q ‘ZB) ‘(fc-p ‘go >q ye) ‘(εp ‘εo >q ‘ZB) ‘(SP ‘CO >q ‘ZB) ‘(LP ‘CO >q 7B) ‘(S3P ‘30 >q ‘ze) ‘(kSP ‘30 >q ‘ze) ‘(OSP ‘30 >q ZB) ‘(6LP ‘30 >q ‘ze) ‘(gkp ‘so >q ‘ZB) ‘(ZLP ‘30 >q 7B) ‘(9LP ‘30 >q ZB) ‘(gLP ‘SO >q ‘ze) ‘(^kp ‘so >q ‘ze) ‘(gLP ‘30 >q ‘ZB) ‘(SLP ‘30 >q b6, c2, d4), (a7, b6, c2, d5), (a7, b6, c2, d6), (a7, b6, c2, d7), (a7, b6, c2, d8), (a7, b6, c2, d9), (a7, b6, c2, d10), (a7, b6, c2, d11), (a7, b6, c2, d12), (a7, b6, c2, d13), (a7, b6, c2, d14), (a7, b6, c2, d15), (a7, b6, c2, d16), (a7, b6, c2, d17), (a7, b6, c2, d18), (a7, b6, c2, d19), (a7, b6, c2, d20), (a7, b6, c2, d21), (a7, b6, c2, d22), (a7, b6, c3, d1), (a7, b6, c3, d2), (a7, b6, c3, d3), (a7, b6, c3, d4), (a7, b6, c3, d5), (a7, b6, c3, d6), (a7, b6, c3, d7), (a7, b6, c3, d8), (a7, b6, c3, d9), (a7, b6, c3, d10), (a7, b6, c3, d11), (a7, b6, c3, d12), (a7, b6, c3, d13), (a7, b6, c3, d14), (a7, b6, c3, d15), (a7, b6, c3, d16), (a7, b6, c3, d17), (a7, b6, c3, d18), (a7, b6, c3, d19), (a7, b6, c3, d20), (a7, b6, c3, d21), (a7, b6, c3, d22), (a8, b1, c1, d1), (a8, b1, c1, d2), (a8, b1, c1, d3), (a8, b1, c1, d4), (a8, b1, c1, d5), (a8, b1, c1, d6), (a8, b1, c1, d7), (a8, b1, c1, d8), (a8, b1, c1, d9), (a8, b1, c1, d10), (a8, b1, c1, d11), (a8, b1, c1, d12), (a8, b1, c1, d13), (a8, b1, c1, d14), (a8, b1, c1, d15), (a8, b1, c1, d16), (a8, b1, c1, d17), (a8, b1, c1, d18), (a8, b1, c1, d19), (a8, b1, c1, d20), (a8, b1, c1, d21), (a8, b1, c1, d22), (a8, b1, c2, d1), (a8, b1, c2, d2), (a8, b1, c2, d3), (a8, b1, c2, d4), (a8, b1, c2, d5), (a8, b1, c2, d6), (a8, b1, c2, d7), (a8, b1, c2, d8), (a8, b1, c2, d9), (a8, b1, c2, d10), (a8, b1, c2, d11), (a8, b1, c2, d12), (a8, b1, c2, d13), (a8, b1, c2, d14), (a8, b1, c2, d15), (a8, b1, c2, d16), (a8, b1, c2, d17), (a8, b1, c2, d18), (a8, b1, c2, d19), (a8, b1, c2, d20), (a8, b1, c2, d21), (a8, b1, c2, d22), (a8, b1, c3, d1), (a8, b1, c3, d2), (a8, b1, c3, d3), (a8, b1, c3, d4), (a8, b1, c3, d5), (a8, b1, c3, d6), (a8, b1, c3, d7), (a8, b1, c3, d8), (a8, b1, c3, d9), (a8, b1, c3, d10), (a8, b1, c3, d11), (a8, b1, c3, d12), (a8, b1, c3, d13), (a8, b1, c3, d14), (a8, b1, c3, d15), (a8, b1, c3, d16), (a8, b1, c3, d17), (a8, b1, c3, d18), (a8, b1, c3, d19), (a8, b1, c3, d20), (a8, b1, c3, d21), (a8, b1, c3, d22), (a8, b2, c1, d1), (a8, b2, c1, d2), (a8, b2, c1, d3), (a8, b2, c1, d4), (a8, b2, c1, d5), (a8, b2, c1, d6), (a8, b2, c1, d7), (a8, b2, c1, d8), (a8, b2, c1, d9), (a8, b2, c1, d10), (a8, b2, c1, d11), (a8, b2, c1, d12), (a8, b2, c1, d13), (a8, b2, c1, d14), (a8, b2, c1, d15), (a8, b2, c1, d16), (a8, b2, c1, d17), (a8, b2, c1, d18), (a8, b2, c1, d19), (a8, b2, c1, d20), (a8, b2, c1, d21), (a8, b2, c1, d22), (a8, b2, c2, d1), (a8, b2, c2, d2), (a8, b2, c2, d3), (a8, b2, c2, d4), (a8, b2, c2, d5), (a8, b2, c2, d6), (a8, b2, c2, d7), (a8, b2, c2, d8), (a8, b2, c2, d9), (a8, b2, c2, d10), (a8, b2, c2, d11), (a8, b2, c2, d12), (a8, b2, c2, d13), (a8, b2, c2, d14), (a8, b2, c2, d15), (a8, b2, c2, d16), (a8, b2, c2, d17), (a8, b2, c2, d18), (a8, b2, c2, d19), (a8, b2, c2, d20), (a8, b2, c2, d21), (a8, b2, c2, d22), (a8, b2, c3, d1), (a8, b2, c3, d2), (a8, b2, c3, d3), (a8, b2, c3, d4), (a8, b2, c3, d5), (a8, b2, c3, d6), (a8, b2, c3, d7), (a8, b2, c3, d8), (a8, b2, c3, d9), (a8, b2, c3, d10), (a8, b2, c3, d11), (a8, b2, c3, d12), (a8, b2, c3, d13), (a8, b2, c3, d14), (a8, b2, c3, d15), (a8, b2, c3, d16), (a8, b2, c3, d17), (a8, b2, c3, d18), (a8, b2, c3, d19), (a8, b2, c3, d20), (a8, b2, c3, d21), (a8, b2, c3, d22), (a8, b3, c1, d1), (a8, b3, c1, d2), (a8, b3, c1, d3), (a8, b3, c1, d4), (a8, b3, c1, d5), (a8, b3, c1, d6), (a8, b3, c1, d7), (a8, b3, c1, d8), (a8, b3, c1, d9), (a8, b3, c1, d10), (a8, b3, c1, d11), (a8, b3, c1, d12), (a8, b3, c1, d13), (a8, b3, c1, d14), (a8, b3, c1, d15), (a8, b3, c1, d16), (a8, b3, c1, d17), (a8, b3, c1, d18), (a8, b3, c1, d19), (a8, b3, c1, d20), (a8, b3, c1, d21), (a8, b3, c1, d22), (a8, b3, c2, d1), (a8, b3, c2, d2), (a8, b3, c2, d3), (a8, b3, c2, d4), (a8, b3, c2, d5), (a8, b3, c2, d6), (a8, b3, c2, d7), (a8, b3, c2, d8), (a8, b3, c2, d9), (a8, b3, c2, d10), (a8, b3, c2, d11), (a8, b3, c2, d12), (a8, b3, c2, d13), (a8, b3, c2, d14), (a8, b3, c2, d15), (a8, b3, c2, d16), (a8, b3, c2, d17), (a8, b3, c2, d18), (a8, b3, c2, d19), (a8, b3, c2, d20), (a8, b3, c2, d21), (a8, b3, c2, d22), (a8, b3, c3, d1), (a8, b3, c3, d2), (a8, b3, c3, d3), (a8, b3, c3, d4), (a8, b3, c3, d5), (a8, b3, c3, d6), (a8, b3, c3, d7), (a8, b3, c3, d8), (a8, b3, c3, d9), (a8, b3, c3, d10), (a8, b3, c3, d11), (a8, b3, c3, d12), (a8, b3, c3, d13), (a8, b3, c3, d14), (a8, b3, c3, d15), (a8, b3, c3, d16), (a8, b3, c3, d17), (a8, b3, c3, d18), (a8, b3, c3, d19), (a8, b3, c3, d20), (a8, b3, c3, d21), (a8, b3, c3, d22), (a8, b4, c1, d1), (a8, b4, c1, d2), (a8, b4, c1, d3), (a8, b4, c1, d4), (a8, b4, c1, d5), (a8, b4, c1, d6), (a8, b4, c1, d7), (a8, b4, c1, d8), (a8, b4, c1, d9), (a8, b4, c1, d10), (a8, b4, c1, d11), (a8, b4, c1, d12), (a8, b4, c1, d13), (a8, b4, c1, d14), (a8, b4, c1, d15), (a8, b4, c1, d16), (a8, b4, c1, d17), (a8, b4, c1, d18), (a8, b4, c1, d19), (a8, b4, c1, d20), (a8, b4, c1, d21), (a8, b4, c1, d22), (a8, b4, c2, d1), (a8, b4, c2, d2), (a8, b4, c2, d3), (a8, b4, c2, d4), (a8, b4, c2, d5), (a8, b4, c2, d6), (a8, b4, c2, d7), (a8, b4, c2, d8), (a8, b4, c2, d9), (a8, b4, c2, d10), (a8, b4, c2, d11), (a8, b4, c2, d12), (a8, b4, c2, d13), (a8, b4, c2, d14), (a8, b4, c2, d15), (a8, b4, c2, d16), (a8, b4, c2, d17), (a8, b4, c2, d18), (a8, b4, c2, d19), (a8, b4, c2, d20), (a8, b4, c2, d21), (a8, b4, c2, d22), (a8, b4, c3, d1), (a8, b4, c3, d2), (a8, b4, c3, d3), (a8, b4, c3, d4), (a8, b4, c3, d5), (a8, b4, c3, d6), (a8, b4, c3, d7), (a8, b4, c3, d8), (a8, b4, c3, d9), (a8, b4, c3, d10), (a8, b4, c3, d11), (a8, b4, c3, d12), (a8, b4, c3, d13), (a8, b4, c3, d14), (a8, b4, c3, d15), (a8, b4, c3, d16), (a8, b4, c3, d17), (a8, b4, c3, d18), (a8, b4, c3, d19), (a8, b4, c3, d20), (a8, b4, c3, d21), (a8, b4, c3, d22), (a8, b5, c1, d1), (a8, b5, c1, d2), (a8, b5, c1, d3), (a8, b5, c1, d4), (a8, b5, c1, d5), (a8, b5, c1, d6), (a8, b5, c1, d7), (a8, b5, c1, d8), (a8, b5, c1, d9), (a8, b5, c1, d10), (a8, b5, c1, d11), (a8, b5, c1, d12), (a8, b5, c1, d13), (a8, b5, c1, d14), (a8, b5, c1, d15), (a8, b5, c1, d16), (a8, b5, c1, d17), (a8, b5, c1, d18), (a8, b5, c1, d19), (a8, b5, c1, d20), (a8, b5, c1, d21), (a8, b5, c1, d22), (a8, b5, c2, d1), (a8, b5, c2, d2), (a8, b5, c2, d3), (a8, b5, c2, d4), (a8, b5, c2, d5), (a8, b5, c2, d6), (a8, b5, c2, d7), (a8, b5, c2, d8), (a8, b5, c2, d9), (a8, b5, c2, d10), (a8, b5, c2, d11), (a8, b5, c2, d12), (a8, b5, c2, d13), (a8, b5, c2, d14), (a8, b5, c2, d15), (a8, b5, c2, d16), (a8, b5, c2, d17), (a8, b5, c2, d18), (a8, b5, c2, d19), (a8, b5, c2, d20), (a8, b5, c2, d21), (a8, b5, c2, d22), (a8, b5, c3, d1), (a8, b5, c3, d2), (a8, b5, c3, d3), (a8, b5, c3, d4), (a8, b5, c3, d5), (a8, b5, c3, d6), (a8, b5, c3, d7), (a8, b5, c3, d8), (a8, b5, c3, d9), (a8, b5, c3, d10), (a8, b5, c3, d11), (a8, b5, c3, d12), (a8, b5, c3, d13), (a8, b5, c3, d14), (a8, b5, c3, d15), (a8, b5, c3, d16), (a8, b5, c3, d17), (a8, b5, c3, d18), (a8, b5, c3, d19), (a8, b5, c3, d20), (a8, b5, c3, d21), (a8, b5, c3, d22), (a8, b6, c1, d1), (a8, b6, c1, d2), (a8, b6, c1, d3), (a8, b6, c1, d4), (a8, b6, c1, d5), (a8, b6, c1, d6), (a8, b6, c1, d7), (a8, b6, c1, d8), (a8, b6, c1, d9), (a8, b6, c1, d10), (a8, b6, c1, d11), (a8, b6, c1, d12), (a8, b6, c1, d13), (a8, b6, c1, d14), (a8, b6, c1, d15), (a8, b6, c1, d16), (a8, b6, c1, d17), (a8, b6, c1, d18), (a8, b6, c1, d19), (a8, b6, c1, d20), (a8, b6, c1, d21), (a8, b6, c1, d22), (a8, b6, c2, d1), (a8, b6, c2, d2), (a8, b6, c2, d3), (a8, b6, c2, d4), (a8, b6, c2, d5), (a8, b6, c2, d6), (a8, b6, c2, d7), (a8, b6, c2, d8), (a8, b6, c2, d9), (a8, b6, c2, d10), (a8, b6, c2, d11), (a8, b6, c2, d12), (a8, b6, c2, d13), (a8, b6, c2, d14), (a8, b6, c2, d15), (a8, b6, c2, d16), (a8, b6, c2, d17), (a8, b6, c2, d18), (a8, b6, c2, d19), (a8, b6, c2, d20), (a8, b6, c2, d21), (a8, b6, c2, d22), (a8, b6, c3, d1), (a8, b6, c3, d2), (a8, b6, c3, d3), (a8, b6, c3, d4), (a8, b6, c3, d5), (a8, b6, c3, d6), (a8, b6, c3, d7), (a8, b6, c3, d8), (a8, b6, c3, d9), (a8, b6, c3, d10), (a8, b6, c3, d11), (a8, b6, c3, d12), (a8, b6, c3, d13), (a8, b6, c3, d14), (a8, b6, c3, d15), (a8, b6, c3, d16), (a8, b6, c3, d17), (a8, b6, c3, d18), (a8, b6, c3, d19), (a8, b6, c3, d20), (a8, b6, c3, d21), (a8, b6, c3, d22), (a9, b1, c1, d1), (a9, b1, c1, d2), (a9, b1, c1, d3), (a9, b1, c1, d4), (a9, b1, c1, d5), (a9, b1, c1, d6), (a9, b1, c1, d7), (a9, b1, c1, d8), (a9, b1, c1, d9), (a9, b1, c1, d10), (a9, b1, c1, d11), (a9, b1, c1, d12), (a9, b1, c1, d13), (a9, b1, c1, d14), (a9, b1, c1, d15), (a9, b1, c1, d16), (a9, b1, c1, d17), (a9, b1, c1, d18), (a9, b1, c1, d19), (a9, b1, c1, d20), (a9, b1, c1, d21), (a9, b1, c1, d22), (a9, b1, c2, d1), (a9, b1, c2, d2), (a9, b1, c2, d3), (a9, b1, c2, d4), (a9, b1, c2, d5), (a9, b1, c2, d6), (a9, b1, c2, d7), (a9, b1, c2, d8), (a9, b1, c2, d9), (a9, b1, c2, d10), (a9, b1, c2, d11), (a9, b1, c2, d12), (a9, b1, c2, d13), (a9, b1, c2, d14), (a9, b1, c2, d15), (a9, b1, c2, d16), (a9, b1, c2, d17), (a9, b1, c2, d18), (a9, b1, c2, d19), (a9, b1, c2, d20), (a9, b1, c2, d21), (a9, b1, c2, d22), (a9, b1, c3, d1), (a9, b1, c3, d2), (a9, b1, c3, d3), (a9, b1, c3, d4), (a9, b1, c3, d5), (a9, b1, c3, d6), (a9, b1, c3, d7), (a9, b1, c3, d8), (a9, b1, c3, d9), (a9, b1, c3, d10), (a9, b1, c3, d11), (a9, b1, c3, d12), (a9, b1, c3, d13), (a9, b1, c3, d14), (a9, b1, c3, d15), (a9, b1, c3, d16), (a9, b1, c3, d17), (a9, b1, c3, ‘6B) ‘(OLP ‘εo ‘εq ‘6θ) ‘(ΘP ‘εo ‘εq ‘6θ) ‘(SP ‘εo ‘εq ‘6θ) ‘(ZP ‘εo ‘εq ‘6θ) ‘(9P ‘εo ‘εq ‘6θ) ‘(SP ‘εo ‘εq ‘6θ) ‘(^P ‘εo ‘εq ‘6θ) ‘(εp ‘εo ‘εq ‘6θ) ‘(SP ‘εo ‘εq ‘6θ) ‘(LP ‘εo ‘εq ‘6θ) ‘(33P ‘30 ‘εq ‘θe) ‘(LSP ‘30 ‘εq ‘6θ) ‘(OSP ‘30 ‘εq ‘6θ) ‘(6LP ‘30 ‘εq ‘6θ) ‘(8LP ‘30 ‘εq ‘6θ) ‘(ZLP ‘30 ‘εq ‘6θ) ‘(9LP ‘30 ‘εq ‘6θ) ‘(SLP ‘30 ‘εq ‘6θ) ‘(^LP ‘30 ‘εq ‘6θ) ‘(εLP ‘30 ‘εq ‘6θ) ‘(SLP ‘30 ‘εq ‘6θ) ‘(LLP ‘30 ‘εq ‘6θ) ‘(OLP ‘30 ‘εq ‘6θ) ‘(OP ‘30 ‘εq ‘6θ) ‘(SP ‘30 ‘εq ‘6B) ‘(ZP ‘30 ‘εq ‘6θ) ‘(9P ‘30 ‘εq ‘6θ) ‘(SP ‘30 ‘εq ‘6θ) ‘(^P ‘30 ‘εq ‘6θ) ‘(εp ‘30 ‘εq ‘6θ) ‘(SP ‘30 ‘εq ‘6θ) ‘(LP ‘30 ‘εq ‘6θ) ‘(SSP ‘LO ‘εq ‘6θ) ‘(LSP ‘LO ‘εq ‘6θ) ‘(OSP ‘LO ‘εq ‘6θ) ‘(OLP ‘LO ‘εq ‘6θ) ‘(SLP ‘LO ‘εq ‘6θ) ‘(ZLP ‘LO ‘εq ‘6θ) ‘(9LP ‘LO ‘εq ‘6θ) ‘(SLP ‘LO ‘εq ‘6θ) ‘(^LP ‘LO ‘εq ‘6θ) ‘(SLP ‘LO ‘εq ‘6θ) ‘(SLP ‘LO ‘εq ‘6θ) ‘(LLP ‘LO ‘εq ‘6θ) ‘(OLP ‘LO ‘εq ‘6θ) ‘(ΘP ‘ LO ‘εq ‘6θ) ‘(SP ‘ LO ‘εq ‘6θ) ‘(ZP ‘ LO ‘εq ‘6θ) ‘(ΘP ‘ LO ‘εq ‘6θ) ‘(SP ‘ LO ‘εq ‘θe) ‘(17P ‘LO ‘εq ‘6θ) ‘(εp ‘LO ‘εq ‘6θ) ‘(SP ‘LO ‘εq ‘6θ) ‘(LP ‘LO ‘εq ‘6θ) ‘(33P ‘εo ‘3q ‘6θ) ‘(L3P ‘εo ‘3q ‘6θ) ‘(03P ‘εo ‘3q ‘6θ) ‘(6LP ‘εo ‘3q ‘6θ) ‘(SLP ‘εo ‘sq ‘6θ) ‘(ZLP ‘εo ‘sq ‘6θ) ‘(9LP ‘εo ‘sq ‘6θ) ‘(SLP ‘εo ‘sq ‘6θ) ‘(np ‘εo ‘sq ‘6θ) ‘(CLP ‘εo ‘sq ‘6θ) ‘(SLP ‘εo ‘sq ‘6θ) ‘(LLP ‘εo ‘sq ‘6θ) ‘(OLP ‘εo ‘sq ‘6θ) ‘(6P ‘εo ‘sq ‘6θ) ‘(SP ‘εo ‘sq ‘6θ) ‘(ZP ‘εo ‘sq ‘6θ) ‘(ΘP ‘εo ‘sq ‘6θ) ‘(SP ‘εo ‘sq ‘6θ) ‘(^P ‘εo ‘sq ‘6θ) ‘(εp ‘εo ‘sq ‘6θ) ‘(SP ‘εo ‘3q ‘6θ) ‘(LP ‘εo ‘sq ‘6θ) ‘(SSP ‘30 ‘sq ‘6θ) ‘(LSP ‘30 ‘sq ‘6θ) ‘(OSP ‘30 ‘sq ‘6θ) ‘(6LP ‘30 ‘3q ‘6θ) ‘(SLP ‘30 ‘sq ‘6θ) ‘(ZLP ‘30 ‘sq ‘6θ) ‘(9LP ‘30 ‘sq ‘6θ) ‘(SLP ‘30 ‘3q ‘6θ) ‘(HP ‘30 ‘sq ‘6θ) ‘(SLP ‘30 ‘sq ‘6θ) ‘(3LP ‘30 ‘sq ‘6B) ‘(LLP ‘30 ‘3q ‘6θ) ‘(OLP ‘30 ‘sq ‘6θ) ‘(6P ‘30 ‘3q ‘6θ) ‘(8P ‘30 ‘3q ‘6θ) ‘(ZP ‘30 ‘3q ‘6θ) ‘(9P ‘30 ‘3q ‘6θ) ‘(SP ‘30 ‘3q ‘6θ) ‘(^P ‘30 ‘3q ‘6θ) ‘(8P ‘30 ‘3q ‘6θ) ‘(3P ‘30 ‘3q ‘6θ) ‘(LP ‘30 ‘3q ‘6θ) ‘(33P ‘LO ‘sq ‘θe) ‘(L3P ‘LO ‘3q ‘6θ) ‘(03P ‘LO ‘sq ‘6θ) ‘(6LP ‘LO ‘sq ‘θe) ‘(gLP ‘LO ‘sq ‘θB) ‘(ZLP ‘LO ‘3q ‘6θ) ‘(9LP ‘LO ‘sq ‘6θ) ‘(SLP ‘LO ‘sq ‘6θ) ‘(^LP ‘LO ‘sq ‘6θ) ‘(8LP ‘LO ‘3q ‘6θ) ‘(3LP ‘LO ‘sq ‘6θ) ‘(LLP ‘LO ‘sq ‘6θ) ‘(OLP ‘LO ‘sq ‘6θ) ‘(6P ‘LO ‘sq ‘6θ) ‘(8P ‘LO ‘sq ‘6θ) ‘(ZP ‘LO ‘sq ‘6θ) ‘(9P ‘LO ‘sq ‘6θ) ‘(SP ‘LO ‘sq ‘6θ) ‘(17P ‘LO ‘sq ‘6θ) ‘(εp ‘LO ‘sq ‘6θ) ‘(SP ‘LO ‘sq ‘6θ) ‘(LP ‘LO ‘sq ‘6θ) ‘(SSP ‘εo %q ‘6B) ‘(LSP ‘εo ‘Lq ‘6θ) ‘(03P ‘εo ‘Lq ‘6θ) ‘(6LP ‘εo ‘Lq ‘6θ) ‘(8LP ‘go ‘gq ‘θB) ‘(sp ‘go ‘gq ‘6θ) ‘(UP ‘εo ‘gq ‘6θ) ‘(33P ‘30 ‘gq ‘6θ) ‘(USP ‘30 ‘gq ‘6θ) ‘(OSP ‘30 ‘gq ‘θe) ‘(6UP ‘30 ‘gq ‘θe) ‘(8UP ‘30 ‘gq ‘θe) ‘(ZUP ‘30 ‘gq ‘6θ) ‘(9UP ‘30 ‘gq ‘θe) ‘(gUP ‘30 ‘gq ‘6θ) ‘(^UP ‘30 ‘gq ‘6θ) ‘(CUP ‘30 ‘gq ‘6θ) ‘(3UP ‘30 ‘gq ‘6θ) ‘(LLP ‘30 ‘gq ‘6θ) ‘(OLP ‘30 ‘gq ‘6θ) ‘(6P ‘30 ‘gq ‘6θ) ‘(8P ‘30 ‘gq ‘6θ) ‘(ZP ‘30 ‘gq ‘6θ) ‘(9P ‘30 ‘gq ‘6θ) ‘(gp ‘30 ‘gq ‘6θ) ‘(frP ‘30 ‘gq ‘6θ) ‘(SP ‘30 ‘gq ‘6θ) ‘(3P ‘30 ‘gq ‘6θ) ‘(LP ‘30 ‘gq ‘6θ) ‘(33P ‘LO ‘gq 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d15), (a90, b5, c1, d16), (a90, b5, c1, d17), (a90, b5, c1, d18), (a90, b5, c1, d19), (a90, b5, c1, d20), (a90, b5, c1, d21), (a90, b5, c1, d22), (a90, b5, c2, d1), (a90, b5, c2, d2), (a90, b5, c2, d3), (a90, b5, c2, d4), (a90, b5, c2, d5), (a90, b5, c2, d6), (a90, b5, c2, d7), (a90, b5, c2, d8), (a90, b5, c2, d9), (a90, b5, c2, d10), (a90, b5, c2, d11), (a90, b5, c2, d12), (a90, b5, c2, d13), (a90, b5, c2, d14), (a90, b5, c2, d15), (a90, b5, c2, d16), (a90, b5, c2, d17), (a90, b5, c2, d18), (a90, b5, c2, d19), (a90, b5, c2, d20), (a90, b5, c2, d21), (a90, b5, c2, d22), (a90, b5, c3, d1), (a90, b5, c3, d2), (a90, b5, c3, d3), (a90, b5, c3, d4), (a90, b5, c3, d5), (a90, b5, c3, d6), (a90, b5, c3, d7), (a90, b5, c3, d8), (a90, b5, c3, d9), (a90, b5, c3, d10), (a90, b5, c3, d11), (a90, b5, c3, d12), (a90, b5, c3, d13), (a90, b5, c3, d14), (a90, b5, c3, d15), (a90, b5, c3, d16), (a90, b5, c3, d17), (a90, b5, c3, d18), (a90, b5, c3, d19), (a90, b5, c3, d20), (a90, b5, c3, d21), (a90, b5, c3, d22), (a90, b6, c1, d1), (a90, b6, c1, d2), (a90, b6, c1, d3), (a90, b6, c1, d4), (a90, b6, c1, d5), (a90, b6, c1, d6), (a90, b6, c1, d7), (a90, b6, c1, d8), (a90, b6, c1, d9), (a90, b6, c1, d10), (a90, b6, c1, d11), (a90, b6, c1, d12), (a90, b6, c1, d13), (a90, b6, c1, d14), (a90, b6, c1, d15), (a90, b6, c1, d16), (a90, b6, c1, d17), (a90, b6, c1, d18), (a90, b6, c1, d19), (a90, b6, c1, d20), (a90, b6, c1, d21), (a90, b6, c1, d22), (a90, b6, c2, d1), (a90, b6, c2, d2), (a90, b6, c2, d3), (a90, b6, c2, d4), (a90, b6, c2, d5), (a90, b6, c2, d6), (a90, b6, c2, d7), (a90, b6, c2, d8), (a90, b6, c2, d9), (a90, b6, c2, d10), (a90, b6, c2, d11), (a90, b6, c2, d12), (a90, b6, c2, d13), (a90, b6, c2, d14), (a90, b6, c2, d15), (a90, b6, c2, d16), (a90, b6, c2, d17), (a90, b6, c2, d18), (a90, b6, c2, d19), (a90, b6, c2, d20), (a90, b6, c2, d21), (a90, b6, c2, d22), (a90, b6, c3, d1), (a90, b6, c3, d2), (a90, b6, c3, d3), (a90, b6, c3, d4), (a90, b6, c3, d5), (a90, b6, c3, d6), (a90, b6, c3, d7), (a90, b6, c3, d8), (a90, b6, c3, d9), (a90, b6, c3, d10), (a90, b6, c3, d11), (a90, b6, c3, d12), (a90, b6, c3, d13), (a90, b6, c3, d14), (a90, b6, c3, d15), (a90, b6, c3, d16), (a90, b6, c3, d17), (a90, b6, c3, d18), (a90, b6, c3, d19), (a90, b6, c3, d20), (a90, b6, c3, d21), (a90, b6, c3, d22).
[0243] O composto representado pela fórmula geral (A) inclui um isômero ótico do mesmo e um racemato do mesmo.
Exemplos de teste 1 - Atividade inibitória de enzima do composto de teste em EGFR e HER2
[0244] EGFR e HER2 purificadas de um sistema de expressão de células de inseto, e um substrato biotinilado (peptídio sintético de ácido glutâmico:tirosina = 4:1) foram adicionados a uma placa de 384 compartimentos com ATP adicionado à mesma, e uma reação enzimática foi realizada à temperatura ambiente. Depois de completada a reação enzimática, um anticorpo de tirosina anti-fosforilado marcado com európio e estreptavidina marcada com alficocianina foram adicionados, e um resíduo de tirosina fosforilado foi quantificado por um método de fluorescência com resolução temporal.
Preparação do composto de teste
[0245] Um composto de teste foi ajustado em 10 mM usando DMSO.
[0246] Além disso, usando uma solução de DMSO a 10%, foi preparada uma solução 1 mM, e esta foi considerada como o ponto de concentração máxima.
[0247] Como uma série de diluições, foi uma preparada uma série de diluições 4 vezes até o estágio 10.
Preparação do reagente Preparação do tampão:
[0248] Como tampão, foi usado TBS contendo 10 mM MgCl2, 5 mM MnCl2, 0,2 mM Na3VO4, e 0,1% BSA.
Enzima:
[0249] Como enzimas EGFR e HER2, aquelas purificadas de um sistema de expressão de células de inseto foram adquiridas na Carna Biosciences, Inc.
[0250] Uma solução de enzima EGFR foi ajustada em 250 ng/ml usando um tampão.
[0251] A cinase HER2 foi ajustada em 1000 ng/ml usando um tampão.
Solução de substrato:
[0252] Como substrato, foi usado poli-Glu-Tyr biotinilado (4:1, produzido por CISbio). Um concentração foi ajustada em 3,125 μg/ml usando o tampão acima.
Solução de ATP:
[0253] Uma concentração de ATP no estudo da enzima EGFR foi ajustada em 125 μM usando o tampão.
[0254] Uma concentração de ATP no estudo da enzima HER2 foi ajustada em 290 μM.
Reagente de detecção:
[0255] Para preparar um reagente de detecção, foi usado TBS contendo 30mM EDTA, 0,8M KF e 0,1% BSA.
[0256] Um anticorpo de tirosina antifosforilado marcado com európio, PT-66K (CISbio) foi ajustado em 195 ng/ml, e estreptavidina marcada com alficocianina, SA-XL(CISbio) foi ajustada em 5 μg/ml. Método de ensaio
[0257] Como placa de ensaio, foi usada uma placa de 384 compartimentos. Por uma cavidade, foram adicionados 1,1 μl de um composto de teste, 4 μl de uma solução de substrato, e 4 μl de uma solução de enzima, e 2 μl de uma solução de ATP para iniciar uma reação enzimática. A reação enzimática foi realizada à temperatura ambiente por 60 minutos, e 10 μl de um reagente de detecção foram adicionados para completar a reação. Uma hora depois de completada a reação, foi efetuada a medida fluorescente com resolução temporal. Método de avaliação
[0258] Usando 10% DMSO no lugar de um composto de teste, e deixando um sinal com a adição de ATP ser 0% de inibição (atividade enzimática 100%), e deixando um sinal na ausência de ATP ser 100% de inibição (atividade enzimática 0%), foi calculada a atividade inibitória com a adição de um composto de teste.
[0259] A atividade inibitória (valor de IC50, nM) dos compostos descritos nos Exemplos em EGFR e HER2 está mostrada abaixo. Tabela 50
Figure img0269
Figure img0270
Figure img0271
Tabela 51
Figure img0272
Figure img0273
Figure img0274
Exemplo de teste 2 - Teste de inibição de proliferação celular in vitro do composto de teste
[0260] Como a cepa de célula de câncer humano, foi usada a BT-474. As células foram todas cultivadas em uma incubadora a 37°C e 5% de CO2 em um meio no qual 10% de soro fetal bovino (ICN) e 50 unidades/ml de penicilina/50 μg/ml a solução de estreptomicina (GIBCO) foram adicionados ao meio essencial modificado da Dulbecco (DMEM, Nacalai Tesque, Inc). Cada 3000/cavidade de células foram semeadas em uma placa de 96 cavidades (Sumitomo Bakelite Co., Ltd.) e, no dia seguinte, um fármaco foi adicionado a uma concentração máxima de 3 x 10-10 a 10-5M. Depois de cultivadas por 3 dias, o ensaio de WST (sal de tetrazólio solúvel em água) foi realizado, e um valor de IC50 foi calculado.
[0261] A atividade inibitória de proliferação (valor de IC50, nM) dos compostos descritos nos exemplos em BT-474 está mostrada abaixo. Tabela 52
Figure img0275
Figure img0276
Tabela 53
Figure img0277
Figure img0278
Exemplo de teste 3 - Teste de avaliação de antitumor in vivo do composto de teste
[0262] Células NCI-N87 (cepa de células de câncer de estômago humano) foram transplantadas em uma massa de gordura mamária de um camundongo fêmea nu (BALB/cA Jcl-nu/nu, CLEA Japan, Inc.) a 5 x 106células/camundongo (dia 0). No dia 5, um diâmetro comprido e um diâmetro curto de um tumor foram medidos com um compasso, e os camundongos foram divididos em grupo (N = 6) de modo que o tamanho do tumor entre os grupos fosse o mesmo. Um composto de teste (20, 80 mg/kg) suspendido em uma solução de metilcelulose (MC) foi administrado por via oral a partir do dia 5 por 15 dias consecutivos, e o efeito antitumor foi expresso pela proporção (T/C%) de um valor médio do tamanho de tumor entre um grupo medicado com composto (T) e um grupo de controle (C; 0,5% MC) no dia 20.
[0263] Os resultados da avaliação antitumor in vivo de um composto VIII-11 estão mostrados na Tabela 54 e os resultados de uma avaliação antitumor in vivo de um composto VIII-66 estão mostrados na Tabela 55. Tabela 54
Figure img0279
Tabela 55
Figure img0280
Exemplos de preparação Exemplo de preparação 1
[0264] É preparado um grânulo contendo os seguintes ingredientes. Ingrediente Composto representado pela fórmula (I) 10 mg Lactose 700 mg Amido de milho 274 mg HPC-L 16 mg 1000 mg
[0265] O composto representado pela fórmula (I) e lactose são passados por uma peneira de 60 mesh. O amido de milho é passado por uma peneira de 120 mesh. Estes são misturados com uma máquina de misturação tipo V. Uma solução aquosa de HPC-L (hidroxipropilcelulose de baixa viscosidade) é adicionada a um pó da mistura, e este é amassado, granulado (granulação por extrusão, diâmetro de poro 0,5 a 1 mm), e secado. O grânulo seco resultante é peneirado com uma peneira vibratória (12/60 mesh) para obter um grânulo.
Exemplo de preparação 2
[0266] É preparado um pó para encher uma cápsula contendo os seguintes ingredientes. Ingrediente Composto representado pela fórmula (I) 10 mg Lactose 79 mg Amido de milho 10 mg Estearato de magnésio 1 mg 100 mg
[0267] O composto representado pela fórmula (I), e lactose são passados por uma peneira de 60 mesh. O amido de milho é passado por uma peneira de 120 mesh. Estes e o estearato de magnésio são misturados com uma máquina de misturação tipo V. 10 trituração 100 mg são introduzidos em uma cápsula de gelatina dura N° 5.
Exemplo de preparação 3
[0268] É preparado um grânulo para encher uma cápsula contendo os seguintes ingredientes. Ingrediente Composto representado pela fórmula (I) 15 mg Lactose 90 mg Amido de milho 42 mg HPC-L 3 mg 150 mg
[0269] O composto representado pela fórmula (I), e lactose são passados por uma peneira de 60 mesh. O amido de milho é passado por uma peneira de 120 mesh. Estes são misturados, uma solução de HPL-L é adicionada a um pó da mistura, e este é amassado, granulado, e secado. O grânulo seco resultante tem o tamanho ajustado, dos quais 150 mg são introduzidos em uma cápsula de gelatina dura N° 4.
Exemplo de preparação 4
[0270] É preparado um comprimido contendo os seguintes ingredientes. Ingrediente Composto representado pela fórmula (I) 10 mg Lactose 90 mg Celulose microcristalina 30 mg CMC-Na 15 mg Estearato de magnésio 5 mg 150 mg
[0271] O composto representado pela fórmula (I), lactose, celulose microcristalina, CMC-Na (sal sódico de carboximetilcelulose) são passados por uma peneira de 60 mesh e misturados. O estearato de magnésio é misturado em um pó da mistura para obter um pó da mistura para formação de comprimido. O presente pó misturado é diretamente comprimido para obter um comprimido de 150 mg.
Exemplo de preparação 5
[0272] Uma preparação intravenosa é preparada da seguinte maneira: Composto representado pela fórmula (I) 100 mg Glicerídeo de ácidos graxos saturados 1000 ml
[0273] Uma solução dos ingredientes acima é administrada por via intravenosa a um paciente a uma taxa de 1 ml por minuto.
Aplicabilidade Industrial
[0274] Como o presente composto possui a excelente ação de inibir um receptor de EGF e HER2, e é bastante seguro, ele é útila como medicamento, entre outras coisas, como um produto terapêutico para um câncer.

Claims (3)

1. Composto, caracterizado pelo fato de que é representado pela fórmula:
Figure img0281
ou um sal farmaceuticamente aceitável do mesmo.
2. Composição farmacêutica, caracterizada pelo fato de que compreende o composto como definido na reivindicação 1, ou um sal farmaceuticamente aceitável do mesmo, como um ingrediente ativo, e um aditivo farmacêutico.
3. Composição farmacêutica útil para tratar câncer, caracterizada pelo fato de que compreende o composto como definido na reivindicação 1, ou um sal farmaceuticamente aceitável do mesmo, como um ingrediente ativo.
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EP1854789A4 (en) 2009-06-17
RU2414457C2 (ru) 2011-03-20
US8349857B2 (en) 2013-01-08
CN101163684B (zh) 2012-08-29
RU2007135023A (ru) 2009-03-27
AU2006216266C1 (en) 2010-08-26
KR20070098941A (ko) 2007-10-05
PL1854789T3 (pl) 2014-03-31
AU2006216266B2 (en) 2010-02-18
ES2431843T3 (es) 2013-11-28
US8202879B2 (en) 2012-06-19
AU2006216266A2 (en) 2006-08-31
CA2599328A1 (en) 2006-08-31
NO20074311L (no) 2007-11-23
CN101163684A (zh) 2008-04-16
JPWO2006090717A1 (ja) 2008-07-24
AU2006216266A1 (en) 2006-08-31
CA2599328C (en) 2012-04-17
JP4137174B2 (ja) 2008-08-20
BRPI0606905A2 (pt) 2009-07-28
US20090143414A1 (en) 2009-06-04
AU2006216266A8 (en) 2009-04-02
DK1854789T3 (da) 2013-10-21
PT1854789E (pt) 2013-10-23
KR100910333B1 (ko) 2009-07-31
US20120123114A1 (en) 2012-05-17
NO343403B1 (no) 2019-02-25
EP1854789B1 (en) 2013-10-09
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TW200640880A (en) 2006-12-01
EP1854789A1 (en) 2007-11-14

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