DK2507235T3 - Triazolpyrimidiner - Google Patents
Triazolpyrimidiner Download PDFInfo
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- DK2507235T3 DK2507235T3 DK10787274.9T DK10787274T DK2507235T3 DK 2507235 T3 DK2507235 T3 DK 2507235T3 DK 10787274 T DK10787274 T DK 10787274T DK 2507235 T3 DK2507235 T3 DK 2507235T3
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- alkyl
- alkoxy
- halo
- nr8r7
- pyridin
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Claims (17)
1. Forbindelse med generel formel (I):
(I) 5 hvor: R1 er en arylgruppe, som er substitueret en eller flere gange, identisk eller forskelligt, med en substituent, der er udvalgt blandt: R6- (Ci-Cg-alkyl)-, R6- (CH2) n (CHOH) (CH2) m-, R6- (Ci-C6-alkoxy) -, R6- ) (CH2) n (CHOH) (CH2) p-0-, R6- (Ci-C6-alkoxy-Ci-C6-alkyl)-, R6-(Ci-C6- alkoxy-Ci-C6-alkyl)-0-,Rs-0-, -C(=0)R6, -C(=0)0-R6, -0C (=0) -R6, -N (H) C (=0) R6, -N (R7) C (=0) R6, -N (H) C (=0) NR6R7, -N (R7) C (=0) NRSR7, -NR5R7, -C (=0)N(H)R6, -C (=0) NR6R7, R6-S-, R6-S (=0) -, R6-S (=0) 2-, - N (H) S (=0) R6, -N (R7) S (=0) R6, -S (=0) N (H) R6, -S(=0)NR6R7, 5 N (H) S (=0) 2Rb, -N (R7) S (=0) 2R6, -S (=0) 2N (H) R6, -S (=0) 2NR6R7, S (=0) (=NR6) R7, -s (=0) (=NR7) R6, -N=S (=0) (R6) R7; og som eventuelt er substitueret en eller flere gange, identisk eller forskelligt, med en substituent, der er udvalgt blandt: 3 halo-, hydroxyl-, cyano-, nitro-, Ci-C6-alkyl-, halo-Ci-C6-alkyl-, Ci-Cg-alkoxy-, halo-Ci-C6-alkoxy-, hydroxy-Ci-C6-alkyl-, Ci-C6-alkoxy-Ci-C6-alkyl-, halo-Ci-C6-alkoxy-Ci-C6-alkyl-, R8- (C2-Cg-alkyl)-, R8- (CH2) n (CHOH) (CH2) m-, R8- (Ci-C6-alkoxy)-, R8- (CH2) n (CHOH) (CH2) p-0-, R8-(Ci-C6-alkoxy-Ci-C6-alkyl)-, R8- (Ci-C6- 5 alkoxy-Ci-Ce-alkyl)-0-, R8-0-, -C(=0)R8, -C(=0)0-R8, -0C(=0)-R8, -N(H)C (=0)R8, -N(R7)C (=0)R8, -N (H) C (=0) NR8R7, -N (R7) C (=0) NR8R7, -NR8R7, -C (=0)N(H)R8, -C (=0) NR8R7, R8-S-, R8-S (=0) -, R8-S (=0) 2-, -N(H)S(=0)R8, -N (R7) S (=0) R8, -S (=0) N (H) R8, -S(=0)NR8R7, N (H) S (=0) 2R8, -N (R7) S (=0) 2R8, -S (=0) 2N(H)R8, -S (=0) 2NR8R7, ) S (=0) (=NR8) R7, -S (=0) (=NR7) R8, -N=S (=0) (R8) R7; R2 er en arylgruppe eller heteroarylgruppe, som eventuelt er substitueret en eller flere gange, identisk eller forskelligt, med en substituent, der er udvalgt blandt: halo-, hydroxyl-, cyano-, nitro-, Ci-C6-alkyl-, halo-Ci-C6- alkyl-, Ci-C6-alkoxy-, halo-Ci-C6-alkoxy-, hydroxy-Ci-C6_alkyl-, Ci-C6-alkoxy-Ci-C6-alkyl-, halo-Ci-C6-alkoxy-Ci-C6-alkyl-, R8-(Ci — Ce-alkyl)-, R8- (CH2) n (CHOH) (CH2) m-, R8-(Ci-C6-alkoxy) -, R8- (CH2) n (CHOH) (CH2) p-O-, R8-(Ci-C6-alkoxy-Ci-C6-alkyl)R8- (Ci-C6- alkoxy-Ci-Ce-alkyl)-O-, -O- (CH2) n-C (=0) NR8R7, R8-0-, -C(=0)R8, - C (=0) 0-R8, -OC (=0) -R8, -N (H) C (=0) R8, -N (R7) C (=0) R8, N (H) C (=0) NR8R7, -N (R7) C (=0)NR8R7, -NR8R7, -C (=0) N (H) R8, C(=0)NR8R7, r8-s-, R8-S(=0)-, R8-S(=0)2-, -N (H) S (=0) r8, N (R7) S (=0) R8, -S (=0)N (H)R8, -S(=0)NR8R7, -N (H) S (=0) 2R8, N (R7) S (=0) 2R8, -S (=0) 2N (H) R8, -S (=0) 2NR8R7, -S (=0) (=NR8) R7, S (=0) (=NR7) R8, -N=S (=0) (R8) R7; R er et hydrogenatom, et halogenatom eller en hydroxy-, amino-, cyano-, nitro-, Ci-C4-alkyl-, halo-Ci-C4-alkyl-, Ci-C4-alkoxy-, halo-Ci-C4-alkoxy-, hydroxy-Ci-C4-alkyl-, Ci-C4-alkoxy-Ci-C4-alkyl-, halo-Ci-C4-alkoxy-Ci-C4-alkyl-, C2-C6-alkenyl-, C2-C6~ alkynyl-, halo-C2-C6-alkenyl-, halo-C2-C6-alkynyl-, C3-C6- cycloalkyl- eller halo-C3-C6-cycloalkylgruppe; R4 er et hydrogenatom, et halogenatom eller en hydroxy-, amino-, cyano-, nitro-, Ci-C4-alkyl-, halo-Ci-C4-alkyl-, Ci-C4-alkoxy-, halo-Ci-C4-alkoxy-, hydroxy-Ci-C4-alkyl-, Ci-C4-alkoxy-Ci-C4-alkyl-, halo-Ci-C4-alkoxy-Ci-C4-alkyl-, C2-C6-alkenyl-, C2-C6~ alkynyl-, halo-C2-C6-alkenyl-, halo-C2-C6-alkynyl-, C3-C6~ cycloalkyl- eller halo-C3-C6-cycloalkylgruppe; R5 er et hydrogenatom; R6 er en gruppe, der er udvalgt blandt C3-C6-cycloalkyl, 3- til 10-leddet heterocyclyl, aryl, heteroaryl, -(CH2) q- (C3-C6_ cycloalkyl) , -(CH2)q-(3- til 10-leddet heterocyclyl), -(CH2)q- aryl eller -(CH2) q-heteroaryl, hvilken gruppe eventuelt er substitueret en eller flere gange, identisk eller forskelligt, med en substituent, der er udvalgt blandt: halo-, hydroxyl-, cyano-, nitro-, Ci-C6-alkyl-, halo-C!-C6-alkyl-, Ci-C6~alkoxy-, halo-Ci-Ce-alkoxy-, hydroxy-Ci-C6-alkyl-, Ci-C6-alkoxy-Ci-C6-alkyl-, halo-Ci-C6-alkoxy-Ci-C6-alkyl-, R8- (Ci~ Ce-alkyl)-, R8- (CH2) n (CHOH) (CH2) m-, R8- (Ci-C6-alkoxy) -, R8- (CH2) n (CHOH) (CH2)p-0-, R8-(Ci-C6-alkoxy-Ci-C6-alkyl)-, R8- (C^Cg- alkoxy-Ci-Ce-alkyl)-0-, aryl-, R8-0-, -C(=0)R8, -C(=0)0-R8, - OC (=0) -R8, -N (H) C (=0) R8, -N(R7)C(=0)R8, -N (H) C (=0) NR8R7, N (R7) C (=0) NR8R7, -NR8R7, -C(=0)N(H)R8, -C(=0)NR8R7, r8-s-, R8- S (=0)-, R8-S(=0)2-, -N(H) s (=0)R8, -N(R7)S (=0)R8, -S (=0)N(H)R8, -S(=0)NR8R7, -N(H) S (=0)2R8, -N(R7)S (=0)2R8, -S (=0)2N(H)R8, S(=0)2NR8R7, -S (=0) (=NR8)R7, -s (=0) (=NR7)R8, -N=s (=0) (R8)R7; R7 er et hydrogenatom eller en Ci-C6-alkyl- eller C3-C6- cycloalkylgruppe; eller NR6R7 sammen er en 3- til 10-leddet heterocyclylgruppe, som eventuelt er substitueret en eller flere gange, identisk eller forskelligt, med halogen, hydroxy, cyano-, nitro-, C1-C6-alkyl-, halo-Ci-C6-alkyl-, Ci-C6~alkoxy-, halo-Ci-C6-alkoxy-, hydroxy-Ci-C6-alkyl-, Ci-C6-alkoxy-Ci-C6-alkyl-, halo-Ci-C6“ alkoxy-Ci-C6-alkyl-, C2-C6-alkenyl-, C2-C6-alkynyl- eller C3-C6-cycloalkyl- ; R8 er et hydrogenatom eller en Ci-C6-alkyl- eller C3-C6- cycloalkylgruppe; n, m, p uafhængigt af hinanden er et helt tal på 0, 1, 2, 3, 4 eller 5; q er et helt tal på 0, 1, 2 eller 3; eller en stereoisomer, en tautomer, et N-oxid, et hydrat, et solvat eller et salt deraf eller en blanding af disse.
2. Forbindelse ifølge krav 1, hvor: R1 er en arylgruppe, som er substitueret en eller flere gange, identisk eller forskelligt, med en substituent, der er udvalgt blandt: R6- (Ci-Ce-alkyl)-, R6-(CH2) n (CHOH) (CH2)m-, R6- (Ci-C6-alkoxy) -, R6- (CH2) n (CHOH) (CH2)p-0-, R6-(Ci-C6-alkoxy-Ci-C6-alkyl)-, R6-(Ci-C6- alkoxy-Ci-Cg-alkyl)-0-,R6-0-, -C(=0)R6, -C(=0)0-R6, -0C (=0) -R6, -N (H) C (=0) R6, -N (R7) C (=0) R6, -N (H) C (=0) NRSR7, -N (R7) C (=0) NR6R7, -NR6R7, -C (=0)N(H)R6, -C(=0)NR6R7, r6-s-, R6-S (=0) -, R6-S(=0)2-, - N (H) S (=0) R6, -N (R7) S (=0) R6, -S (=0) N (H) R6, -S(=0)NR6R7, N (H) S (=0) 2R6, -N (R7) S (=0) 2R6, -S (=0) 2N (H) R6, -S (=0) 2NR6R7, S (=0) (=NR6) R7, -S (=0) (=NR7) R6, -N=S (=0) (R6) R7; og som eventuelt er substitueret en eller flere gange, identisk eller forskelligt, med en substituent, der er udvalgt blandt: halo-, hydroxyl-, cyano-, nitro-, Ci-C6-alkyl-, halo-Ci-C6-alkyl-, Ci~C6-alkoxy-, halo-Ci-C6-alkoxy-, hydroxy-Ci-C6~alkyl-, Ci-Ce-alkoxy-Cx-Ce-alkyl-, halo-Ci-C6-alkoxy-Ci-C6-alkyl-, R8-(Ci-Cg-alkyl)-, R8- (CH2) n (CHOH) (CH2) m-, R8-(Ci-C6-alkoxy) -, R8- (CH2) n (CHOH) (CH2) p-O-, R8-(Ci-C6-alkoxy-Ci-C6-alkyl)R8- (Ci-C6- alkoxy-Ci-C6-alkyl)-O-, R8-0-, -C(=0)R8, -C(=0)0-R8, -0C(=0)-R8, -N (H) C (=0) R8, -N (R7) C (=0) R8, -N (H) C (=0) NR8R7, -N (R7) C (=0) NR8R7, -NR8R7, -C (=0)N(H)R8, -C (=0) nr8r7, r8-s-, R8-S (=0) -, R8-S (=0) 2~ r -N(H)S(=0)R8, -N (R7) S (=0) R8, -S (=0) N (H) R8, -S(=0)NR8R7, N (H) S (=0) 2R8, -N (R7) S (=0) 2R8, -S (=0) 2N (H) R8, -S (=0) 2NR8R7, S (=0) (=NR8)R7, -S (=0) (=NR7)R8, -N=S (=0) (R8) R7; R2 er en arylgruppe eller heteroarylgruppe, som eventuelt er substitueret en eller flere gange, identisk eller forskelligt, med en substituent, der er udvalgt blandt: halo-, hydroxyl-, cyano-, nitro-, Ci-C6-alkyl-, halo-Ci-C6-alkyl-, Ci-C6~alkoxy-, halo-Ci-C6~alkoxy-, hydroxy-Ci-C6-alkyl-, Ci-C6-alkoxy-Ci-C6-alkyl-, halo-Ci-C6-alkoxy-Ci-C6-alkyl-, R8-(Ci-Ce-alkyl)-, R8- (CH2) n (CHOH) (CH2) m-, R8- (Ci-C6-alkoxy) -, R8- (CH2) n (CHOH) (CH2)p-0-, R8-(Ci-C6~alkoxy-Ci-C6-alkyl)-, R8- (Ci-C6~ alkoxy-Ci-Ce-alkyl)-0-, -0-(CH2)n-C (=0) NR8R7, R8-0-, -C(=0)R8, - C (=0) 0-R8, -0C (=0) -R8, -N (H) C (=0) R8, -N (R7) C (=0) R8, N (H) C (=0) NR8R7, -N(R7)C(=0)NR8R7, -NR8R7, -C (=0) N (H) R8, C(=0)NR8R7, R8-S-, R8-S(=0)-, R8-S (=0) 2-, -N (H) S (=0) R8, N (R7) S (=0) R8, -S (=0) N (H) R8, -S(=0)NR8R7, -N (H) S (=0) 2R8, N (R7) S (=0) 2R8, -S (=0)2N(H)R8, -S (=0) 2NR8R7, -S (=0) (=NR8) R7, S (=0) (=NR7) R8, -N=S (=0) (R8)R7; R3 er et hydrogenatom, et halogenatom eller en hydroxy-, C1-C4-alkyl-, halo-Ci-C4-alkyl- eller Ci-C4-alkoxygruppe; R4 er et hydrogenatom, et halogenatom eller en Ci-C6-alkyl-, halo-Ci-C6-alkyl- eller Ci-Cg-alkoxygruppe; R5 er et hydrogenatom; R6 er en gruppe, der er udvalgt blandt C3-C6_cycloalkyl, 3- til 10-leddet heterocyclyl, aryl, heteroaryl, -(CH2) q- (C3-C6-cycloalkyl) , -(CH2)q-(3- til 10-leddet heterocyclyl), -(CH2)q- aryl, eller -(CH2) q-heteroaryl, hvilken gruppe eventuelt er substitueret en eller flere gange, identisk eller forskelligt, med en substituent, der er udvalgt blandt: halo-, hydroxyl-, cyano-, nitro-, Ci-C6-alkyl-, halo-Ci-C6-alkyl-, Ci-C6-alkoxy-, halo-Ci-C6-alkoxy-, hydroxy-Ci-C6-alkyl-, Ci-C6-alkoxy-Ci-C6-alkyl-, halo-Ci-C6-alkoxy-Ci-C6-alkyl-, R8-(Ci— C6-alkyl)-, R8- (CH2) n (CHOH) (CH2)m-, R8-(Ci-C6-alkoxy)R8- (CH2) n (CHOH) (CH2) p-O-, R8-(Ci-C6-alkoxy-Ci-C6-alkyl)R8- (Ci-C6- alkoxy-Ci-Cg-alkyl)-O-, aryl-, R8-0-, -C(=0)R8, -C(=0)0-R8, - OC (=0) -R8, -N(H) C (=0)R8, -N (R7) C (=0) R8, -N (H) C (=0) NR8R7, N (R7) C (=0) NR8R7, -NR8R7, -C (=0) N (H) R8, -C(=0)NR8R7, R8-S-, R8- S(=0)-, R8-S(=0)2-, -N(H) S (=0)R8, -N (R7) S (=0) R8, -S (=0) N (H) R8, -S(=0)NR8R7, -N (H) S (=0) 2R8, -N (R7) S (=0) 2R8, -S (=0) 2N (H) R8, S(=0)2NR8R7, -S (=0) (=NR8)R7, -S (=0) (=NR7) R8, -N=S (=0) (R8) R7; R7 er et hydrogenatom eller en Ci-C6-alkyl- eller C3-C6- cycloalkylgruppe; eller NR6R7 sammen er en 3- til 10-leddet heterocyclylgruppe, som eventuelt er substitueret en eller flere gange, identisk eller forskelligt, med halogen, hydroxy-, cyano-, nitro-, Ci-C6_alkyl-, halo-Ci-Cg-alkyl-, Ci-C6~alkoxy-, halo-Ci-C6_alkoxy-, hydroxy-Ci-C6-alkyl-, Ci-C6-alkoxy-Ci-C6-alkyl-, halo-Ci-C6-alkoxy-Ci-C6_alkyl-, C2-C6-alkenyl-, C2-C6-alkynyl- eller C3-C6-cycloalkyl-; R8 er et hydrogenatom eller en Ci-C6-alkyl- eller C3-C6- cycloalkylgruppe; n, m, p uafhængigt af hinanden er et helt tal på 0, 1, 2 eller 3; g er et helt tal på 0, 1, 2 eller 3; eller en stereoisomer, en tautomer, et N-oxid, et hydrat, et solvat eller et salt deraf eller en blanding af disse.
3. Forbindelse ifølge krav 1 eller 2, hvor: R1 er en arylgruppe som er substitueret en eller flere gange, identisk eller forskelligt, med en substituent, der er udvalgt blandt: R6- (Ci-C6-alkyl)-, R6- (CH2) n (CHOH) (CH2) m-, R6- (Ci-C6-alkoxy)-, R6- (CH2) n (CHOH) (CH2) p-0-, R6-(Ci-C6-alkoxy-Ci-C6-alkyl)-, R6-(Ci-C6- alkoxy-Ci-C6-alkyl)-0-,R6-0-, -C(=0)R6, -C(=0)0-R6, -0C(=0)-R6, -N (H) C (=0) R6, -N(R7)C(=0)R6, -N (H) C (=0)NRsR7, -N (R7) C (=0) NR6R7, -NR6R7, -c (=0)N(H)R6, -c (=0) nr6r7, r6-s-, r6-s (=0) -, R6-S (=0) 2-, -N (H) S (=0) R6, -N (R7) S (=0) R6, -S (=0) N (H) R6, -S(=0)NR6R7, N (H) S (=0) 2R6, -N (R7) S (=0) 2R6, -S (=0) 2N(H)Rs, -S (=0) 2NR6R7, S(=0) (=NR6) R7,-S (=0) (=NR7) R6, -N=S (=0) (R6)R7; og som eventuelt er substitueret en eller flere gange, identisk eller forskelligt, med en substituent, der er udvalgt blandt: halo-, hydroxyl-, cyano-, nitro-, Ci-C6-alkyl-, halo-Ci-C6-alkyl-, Ci-C6~alkoxy-, halo-Ci-C6-alkoxy-, hydroxy-Ci-C6-alkyl-, Ci-C6-alkoxy-Ci-C6-alkyl-, halo-Ci-C6-alkoxy-Ci-C6-alkyl-, R8- (Ci-Ce-alkyl)-, R8-(CH2) n (CHOH) (CH2)m-, R8- (Ci-C6-alkoxy)-, R8- (CH2) n (CHOH) (CH2)p-0-, R8- (Ci-C6-alkoxy-Ci-C6-alkyl)-, R8- (Ci-C6- alkoxy-Ci-Ce-alkyl)-0-, R8-0-, -C(=0)R8, -C(=0)0-R8, -0C(=0)-R8, -N (H) C (=0) R8, -N (R7) C (=0) R8, -N (H) C (=0) NR8R7, -N (R7) C (=0) NR8R7, -NR8R7, -C (=0)N(H)R8, -C (=0) NR8R7, R8-S-, R8-S (=0) -, R8-S (=0) 2-, - N (H) S (=0) R8, -N (R7) S (=0) R8, -S (=0) N (H) R8, -S(=0)NR8R7, N (H) S (=0) 2R8, -N (R7) S (=0) 2R8, -S (=0) 2N (H) R8, -S (=0) 2NR8R7, S(=0) (=NR8)R7,-s (=0) (=NR7)R8, -N=S (=0) (R8) R7; R er en arylgruppe eller heteroarylgruppe, som eventuelt er substitueret en eller flere gange, identisk eller forskelligt, med en substituent, der er udvalgt blandt: halo-, hydroxyl-, cyano-, nitro-, Ci-C6-alkyl-, halo-Ci-C6-alkyl-, Ci-C6-alkoxy-, halo-Ci-C6-alkoxy-, hydroxy-Ci-C6-alkyl-, Ci-C6-alkoxy-Ci-C6-alkyl-, halo-Ci-C6-alkoxy-Ci-C6-alkyl-, R8- (Ci-Ce-alkyl)-, R8- (CH2) n (CHOH) (CH2)m-, R8-(Ci-C6-alkoxy)-, R8- (CH2)n(CH0H) (CH2)p-0-, R8-(Ci-C6-alkoxy-Ci-C6-alkyl)-, R8- (Ci-C6- alkoxy-Ci-Ce-alkyl)-0-, -0- (CH2) n-C (=0) NR8R7, R8-0-, -C(=0)R8, - C (=0) 0-R8, -0C(=0)-R8, -N (H) C (=0) R8, -N (R7) C (=0) R8, N (H) C (=0) NR8R7, -N (R7) C (=0)NR8R7, -NR8R7, -C (=0) N (H) R8, C(=0)NR8R7, R8-S-, R8-S(=0)-, R8-S(=0)2-, -N(H) S (=0)R8, N (R7) S (=0) R8, -S (=0)N (H)R8, -S(=0)NR8R7, -N (H) S (=0) 2R8, N (R7) S (=0) 2R8, -S (=0)2N(H)R8, -S (=0) 2NR8R7, -S (=0) (=NR8) R7, S (=0) (=NR7) R8, -N=S (=0) (R8)R7; R3, R4 er et hydrogenatom; R5 er et hydrogenatom; R6 er en gruppe, der er udvalgt blandt C3-C6-cycloalkyl, 3- til 10-leddet heterocyclyl, aryl, heteroaryl, -(CH2) q- (C3-C6-cycloalkyl) , — (CH2) q- (3- til 10-leddet heterocyclyl), -(CH2)q- aryl eller - (CH2)q-heteroaryl, hvilken gruppe eventuelt er substitueret en eller flere gange, identisk eller forskelligt, med en substituent, der er udvalgt blandt: halo-, hydroxyl-, cyano-, nitro-, Ci-C6-alkyl-, halo-Ci-C6- alkyl-, Ci-Cg-alkoxy-, halo-Ci-Cg-alkoxy-, hydroxy-Ci-Cg-alkyl-, Ci-C6-alkoxy-Ci-C6-alkyl-, halo-Ci-C6-alkoxy-Ci-C6-alkyl-, R8- (Ci~ C6-alkyl) R8-(CH2) n (CHOH) (CH2)m-, R8-(Cd-Cg-alkoxy)-, R8- (CH2)n(CHOH) (CH2)p-0-, R8-(Ci-C6-alkoxy-Ci-C6-alkyl)R8- (Ci-C6- alkoxy-Ci-C6-alkyl)-O-, aryl-, R8-0-, -C(=0)R8, -C(=0)0-R8, - OC (=0) -R8, -N (H) C (=0) R8, -N (R7) C (=0) R8, -N (H) C (=0) NR8R7, N(R7)C(=0)NR8R7, -NR8R7, -C (=0) N (H) R8, -C(=0)NR8R7, R8-S-, R8- S(=0)-, R8-S(=0)2-, -N (H) S (=0) R8, -N (R7) S (=0) R8, -S (=0) N (H) R8, - S(=0)NR8R7, -N (H) S (=0) 2R8, -N(R7)S (=0)2R8, -S (=0)2N(H)R8, S(=0)2NR8R7, -s (=0) (=NR8)R7, -s (=0) (=NR7)R8, -N=s (=0) (R8) R7; R7 er et hydrogenatom eller en Ci-C6-alkyl- eller C3-C6- cycloalkylgruppe; eller NR6R7 sammen er en 3- til 10-leddet heterocyclylgruppe, som eventuelt er substitueret en eller flere gange, identisk eller forskelligt, med halogen, hydroxy-, cyano-, nitro-, Ci-C6-alkyl-, halo-Ci-C6-alkyl-, Ci-C6-alkoxy-, halo-Ci-C6-alkoxy-, hydroxy-Ci-C6-alkyl-, Ci-C6-alkoxy-Ci-C6-alkyl-, halo-Ci-C6-alkoxy-Ci-C6-alkyl-, C2-C6-alkenyl-, C2-C6-alkynyl- eller C3-C6-cycloalkyl- ; R8 er et hydrogenatom eller en Ci-C6-alkyl- eller C3-C6- cycloalkylgruppe; n er et helt tal på 0 eller 1; m er et helt tal på 0, 1 eller 2; p er et helt tal på 1 eller 2; q er et helt tal på 0, 1 eller 2; eller en stereoisomer, en tautomer, et N-oxid, et hydrat, et solvat eller et salt deraf eller en blanding af disse.
4. Forbindelse ifølge et hvilket som helst af kravene 1, 2 eller 3, hvor: R1 er en phenylgruppe, som er substitueret en eller flere gange, identisk eller forskelligt, med en substituent, der er udvalgt blandt: R6-(Ci-C6-alkoxy)-, R6-0-, -C(=0)R6, -C(=0)0-R6, -N (H) C (=0) R6, - N(H)C(=0)NR6R7, -NRsR7, -C(=0)N(H)R6, -C(=0)NRsR7, Rs-S-, R6- S(=0)2-, -N(H)S(=0)2R6, -S (=0) 2N (H) R6, og som eventuelt er substitueret en eller flere gange, identisk eller forskelligt, med en substituent, der er udvalgt blandt: halo-, hydroxyl-, nitro-, Ci-C6-alkyl-, Ci-C6~alkoxy-, hydroxy-(h-Cg-alkyl-, -N (H) C (=0) R8, -N (H) C (=0) NR8R7, -C (=0) N (H) R8, N (H) S (=0) 2R8; R er en phenylgruppe eller pyridinylgruppe, som eventuelt er substitueret en eller flere gange, identisk eller forskelligt, med en substituent, der er udvalgt blandt: halo-, cyano-, nitro-, Ci-C6-alkyl-, halo-Ci-C6-alkyl-, Ci-Cg-alkoxy-, halo-Ci-C6-alkoxy-, -0- (CH2) n-C (=0) NR8R7, -C (=0) N (H) R8, -C(=0)NR8R7, R8-S-, R8-S(=0)-, R8-S(=0)2-, -N (H) S (=0) R8, N (R7) S (=0) R8, -S (=0)N (H)R8, -S(=0)NR8R7, -S (=0) 2N (H) R8, S(=0)2NR8R7 ; R3, R4, er et hydrogenatom; R5 er et hydrogenatom; R6 er en gruppe, der er udvalgt blandt C3-C6-cycloalkyl, 3- til 10-leddet heterocyclyl, aryl, heteroaryl, -(CH2)q-(C3-Cg-cycloalkyl) , —(CH2) q— (3 — til 10-leddet heterocyclyl), -(CH2)q- aryl, eller -(CH2) q-heteroaryl, hvilken gruppe eventuelt er substitueret en eller flere gange, identisk eller forskelligt, med en substituent, der er udvalgt blandt: halo-, hydroxyl-, cyano-, nitro-, Ci-Cg-alkyl-, halo-Ci-C6-alkyl-, Ci-C6-alkoxy-, halo-Ci-C6-alkoxy-, hydroxy-Ci-C6-alkyl-, Ci-C6-alkoxy-Ci-C6-alkyl-, halo-Ci-Cg-alkoxy-Ci-Cg-alkyl-, N (H) C (=0) R8, -N(R7)C (=0)R8, -N (H) C (=0) NR8R7, -N (R7) C (=0) NR8R7, - nr8r7, -c (=o)n(h)r8, -c(=o)nr8r7, r8-s-, r8-s (=0) -, r8-s(=o)2-; R7 er et hydrogenatom eller en Ci-Cg-alkyl- eller C3-C6- cycloalkylgruppe; eller NRSR7 sammen er en 3- til 10-leddet heterocyclylgruppe, som eventuelt er substitueret en eller flere gange, identisk eller forskelligt, med halogen, hydroxy-, cyano-, nitro-, Ci~ C6-alkyl-, halo-Ci-C6-alkyl-, Ci-Cg-alkoxy-, halo-Ci-Cg-alkoxy-, hydroxy-Ci-C6-alkyl-, Ci-C6-alkoxy-Ci-C6-alkyl-, halo-Ci-Cg-alkoxy-Ci-C6-alkyl-, C2-Cg-alkenyl-, C2-C6-alkynyl- eller Cs-Cg-cycloalkyl-; R8 er et hydrogenatom eller en Ci-Cg-alkyl- eller C3-Cg- cycloalkylgruppe; n er et helt tal på 0 eller 1; q er et helt tal på O, 1 eller 2; eller en stereoisomer, en tautomer, et N-oxid, et hydrat, et solvat eller et salt deraf eller en blanding af disse.
5. Forbindelse ifølge et hvilket som helst af kravene 1, 2, 3 eller 4, der er udvalgt fra gruppen, der består af: N-cyclopropyl-4-[2-(2-methoxyphenylamino)-[1,2,4]triazol[1,5— a]pyridin-6-yl]-benzamid; 3-{2-[(2-cyanophenyl) amino] [1,2,4]triazol[1,5-a]pyridin-6-ylJ-N-phenyIbenzamid; N-(4-{2-[ (2-cyanophenyl) amino] [1,2,4]triazol[1,5-a]pyridin-6-ylJphenyl)-2-[4-(trifluormethyl) phenyl]acetamid; N-(4-{2-[(2-cyanophenyl)amino][l,2,4]triazol[l,5-a]pyridin-6-yl}phenyl)-2-methoxy-2-phenylacetamid; N-(4-{2-[(2-cyanophenyl)amino][l,2,4]triazol[l,5-a]pyridin-6-yl}phenyl)-2-[3-(trifluormethyl)phenyl]acetamid; N-(4-{2-[(2-cyanophenyl)amino][1,2,4]triazol[1,5-a]pyridin-6-yl}phenyl)-2-(2-fluorphenyl)acetamid; N-(4-{2-[(2-cyanophenyl)amino][1,2,4]triazol[1,5-a]pyridin-6-yljphenyl)-2-(3-fluorphenyl)acetamid; N-(4-[2-[(2-cyanophenyl)amino][l,2,4]triazol[l,5-a]pyridin-6-ylJphenyl)-2-(4 — fluorphenyl)acetamid; 1— ((4 —{2 —[(2-cyanophenyl)amino] [l,2,4]triazol[l,5-a]pyridin-6-yl}phenyl)-3-phenylurea; N-(4-{2-[(2-cyanophenyl)amino][l,2,4]triazol[l,5-a]pyridin-6-yljphenyl)-2-(pyridin-3-yl)acetamid; N-(4-{2-[(2-cyanophenyl)amino][l,2,4]triazol[l,5-a]pyridin-6-ylJphenyl)-2-(3-methoxyphenyl)acetamid; N-(4-{2-[(2-cyanophenyl)amino][1,2,4]triazol[1,5-a]pyridin-6-ylJphenyl)-2-(3,4-difluorphenyl)acetamid; N-(4-{2-[(2-cyanophenyl)amino][1,2,4]triazol[1,5-a]pyridin-6-ylJphenyl)-2-phenylacetamid; N-(4-{2-[(2-methoxyphenyl)amino][1,2,4]triazol[1,5-a]pyridin-6-ylJphenyl)-2-phenylacetamid; 2- cyclopropyl-N- (4 —{2 —[ (2- methoxyphenyl)amino][l,2,4]triazol[l,5-a]pyridin-6-ylJphenyl)acetamid; N-(4-{2-[(2-methoxyphenyl)amino][l,2,4]triazol[l,5-a]pyridin- 6-yljphenyl)cyclopropancarboxamid; 2-phenyl-N-[4-(2-{ [2- (trifluormethyl) phenyl]amino} [1,2,4]triazol[1,5-a]pyridin-6-yl) phenyl]acetamid; N-[4-(2 —{ [2-(trifluormethyl) phenyl]amino} [1,2,4]triazol[1,5-a]pyridin-6-yl) phenyl]cyclopropancarboxamid; 2-cyclopropyl-N-[4- (2 — { [2- (trifluormethyl) phenyl]amino} [1,2,4]triazol[1,5-a]pyridin-6-yl)phenyl]acetamid; 2-((4-methylpiperazin-l-yl)-N-[4-(2 —{ [2- (trifluormethyl) phenyl]amino} [1,2,4]triazol[1,5-a]pyridin-6-yl) phenyl]acetamid; 2-((morpholin-4-yl)-N-[4- (2 — { [2- (trifluormethyl) phenyl]amino} [1,2,4]triazol[1,5-a]pyridin-6-yl) phenyl]acetamid; 2-((piperidin-l-yl)-N-[4-(2 —{ [2- (trifluormethyl) phenyl]amino} [1,2,4]triazol[1,5-a]pyridin-6-yl) phenyl]acetamid; 2-amino-2-phenyl-N- [4- (2 —{ [2- (trifluormethyl) phenyl]amino} [1,2,4]triazol[1,5-a]pyridin-6-yl) phenyl]acetamid; 2-((pyridin-3-yl)-N-[4- (2 —{ [2- (trifluormethyl) phenyl]amino} [1,2,4]triazol[1,5-a]pyridin-6-yl) phenyl]acetamid; 2-methoxy-2-phenyl-N-[4- (2 —{ [2- (trifluormethyl) phenyl]amino} [1,2,4]triazol[1,5-a]pyridin-6-yl) phenyl]acetamid; N-(4-{2-[(2-cyano-5-methylphenyl)amino][l,2,4]triazol[l,5-a]pyridin-6-yljphenyl)-2-phenylacetamid; N-(4-{2-[ (2-cyano-3-fluorphenyl) amino] [l,2,4]triazol[l,5-a]pyridin-6-yljphenyl)-2-phenylacetamid; N-(3-{2-[ (2-methoxyphenyl) amino] [l,2,4]triazol[l,5-a]pyridin-β-yljphenyl)-2-phenylacetamid; N-(3-{2-[ (2-methoxyphenyl) amino] [l,2,4]triazol[l,5-a]pyridin-6-yljphenyl)cyclopropancarboxamid; 1-cyclopropyl-N-(3 —{2 —[ (2- methoxyphenyl) amino] [1,2,4]triazol[1,5-a]pyridin-6-yljphenyl)methansulfonamid; N-(3-{2-[ (2-methoxyphenyl) amino] [l,2,4]triazol[l,5-a]pyridin-6-yljphenyl)cyclopropansulfonamid; 1-((3-{2-[ (2-methoxyphenyl) amino] [l,2,4]triazol[l,5-a]pyridin-6-yl}phenyl)-3-phenylurea; N-(3-{2-[ (2-methoxyphenyl) amino] [l,2,4]triazol[l,5-a]pyridin-6-yljphenyl)benzensulfonamid; N-(3-{2-[ (2-methoxyphenyl) amino] [l,2,4]triazol[l,5-a]pyridin-6-yljphenyl)benzamid; N-(3-{2-[(2-methoxyphenyl) amino] [l,2,4]triazol[l,5-a]pyridin-6-yljphenyl)-4-methylpiperazin-l-carboxamid; l-cyclopropyl-3-(3 —{2 —[ (2- methoxyphenyl) amino] [1,2,4]triazol[1,5-a]pyridin-6-yljphenyl)urea; N-(3-{2-[ (2-methoxyphenyl) amino] [l,2,4]triazol[l,5-a]pyridin-6-yljphenyl)morpholin-4-carboxamid; 4-((dimethylamino)-N-(3 —{2 —[ (2- methoxyphenyl) amino] [1,2,4]triazol[1,5-a]pyridin-6-yljphenyl)piperidin-l-carboxamid; 1-((3-{2-[ (2-methoxyphenyl) amino] [l,2,4]triazol[l,5-a]pyridin-6-yljphenyl)-3-pyridin-3-ylurea; 1-((3-{2-[ (2-methoxyphenyl) amino] [l,2,4]triazol[l,5-a]pyridin-6-yljphenyl)-3-[2-(morpholin-4-yl)ethyl]urea; 1- ((3-{2-[ (2-methoxyphenyl) amino] [l,2,4]triazol[l,5-a]pyridin-6-yljphenyl)-3-pyridin-4-ylurea; 2- [((6-{3-[(4-methylpiperazin-l- yl) carbonyl]phenyl} [1,2,4]triazol[1,5-a]pyridin-2-yl) amino]benzonitril; 3- {2-[(2-cyanophenyl) amino] [1,2,4]triazol[1,5-a]pyridin-6-ylj-N-cyclopentyIbenzamid; 3-{2-[ (2-cyanophenyl) amino] [1,2,4]triazol[1,5-a]pyridin-6-ylj-N-(l-methylpiperidin-4-yl)benzamid; N-benzyl-3-{2-[ (2-cyanophenyl) amino] [l,2,4]triazol[l,5-a]pyridin-6-yljbenzamid; 3-{2-[ (2-cyanophenyl) amino] [1,2,4]triazol[1,5-a]pyridin-6-ylj-N-cyclopropylbenzamid; N-cyclopropyl-3-{2-[(2-methoxyphenyl) amino] [l,2,4]triazol[l,5-a]pyridin-6-yljbenzamid og N-benzyl-3-{2-[(2-methoxyphenyl) amino] [l,2,4]triazol[l,5-a]pyridin-6-yl}benzamid.
6. Fremgangsmåde til fremstilling af en forbindelse med generel formel (I) ifølge et hvilket som helst af kravene 1 til 5, i hvilken fremgangsmåde en mellemforbindelse med generel formel (5):
(5) hvor R1, R3, R4 og R5 er som defineret for forbindelsen med generel formel (I) i et hvilket som helst af kravene 1 til 5, får mulighed for at reagere med et arylhalid med generel formel (5a): R2-Y (5a) hvor R2 er som defineret for forbindelsen med generel formel (I) i et hvilket som helst af kravene 1 til 5, og Y er en fraspaltelig enhed, såsom for eksempel et halogenatom eller en trifluormethylsulfonyloxy- eller nonafluorbutylsulfonyloxygruppe, til således tilvejebringelse af en forbindelse med generel formel (I):
(I) hvor R1, R2, R3, R4 og R5 er som defineret for forbindelsen med generel formel (I) i et hvilket som helst af kravene 1 til 5.
7. Fremgangsmåde til fremstilling af en forbindelse med generel formel (I) ifølge et hvilket som helst af kravene 1 til 5, i hvilken fremgangsmåde en mellemforbindelse med generel formel (7):
(7) hvor R2, R3, R4 og R5 er som defineret for forbindelsen med generel formel (I) i et hvilket som helst af kravene 1 til 5, og Rla er en arylgruppe, hvortil er bundet en -NH2-substituent, får mulighed for at reagere med en forbindelse med generel formel (7a) : Rlb-X (7a) hvor Rlb er -C(=0)R6, -C(=0)NR6R7, -S(=0)R6, -S(=0)2R6, og X er en egnet funktionel gruppe, via hvilken Rlb i Rlb-X-forbindelsen (7a) kan kobles ved hjælp af en koblingsreaktion, såsom for eksempel en amidkoblingsreaktion, til -NH2-substituenten, der er bundet til arylgruppen Rla i forbindelse (7), hvorved X substitueres med Rla, til således tilvejebringelse af en forbindelse med generel formel (I):
(l) hvor R1, R2, R3, R4 og R5 er som defineret for forbindelsen med generel formel (I) i et hvilket som helst af kravene 1 til 5.
8. Forbindelse med generel formel (I) eller en stereoisomer, en tautomer, et N-oxid, et hydrat, et solvat eller et salt deraf, fortrinsvis et farmaceutisk acceptabelt salt deraf eller en blanding af disse ifølge et hvilket som helst af kravene 1 til 5 til anvendelse til behandling eller profylakse af en sygdom.
9. Forbindelse til anvendelse ifølge krav 8, hvor sygdommen er en sygdom med ukontrolleret cellevækst, -proliferation og/eller -overlevelse, en upassende cellulær immunrespons eller en upassende cellulær inflammatorisk respons, fortrinsvis hvor den ukontrollerede cellevækst, -proliferation og/eller -overlevelse, den upassende cellulære immunrespons eller den upassende cellulære inflammatoriske respons medieres af Mps-1, mere fortrinsvis hvor sygdommen med ukontrolleret cellevækst, -proliferation og/eller -overlevelse, upassende cellulær immunrespons eller upassende cellulær inflammatoriske respons er en hæmotologisk tumor, en fast tumor og/eller metastaser deraf, f.eks. leukæmier og myelodysplastisk syndrom, maligne lymfomer, hoved- og halstumorer herunder hjernetumorer og hjernemetastaser, tumorer i thorax, herunder ikke-småcellede og småcellede lungetumorer, gastrointestinale tumorer, endokrine tumorer, brysttumorer og andre gynækologiske tumorer, urologiske tumorer, herunder nyre-, blære- og prostatatumorer, hudtumorer, og sarkomer og/eller metastaser deraf.
10. Farmaceutisk præparat, der omfatter en forbindelse med generel formel (I) eller en stereoisomer, en tautomer, et N-oxid, et hydrat, et solvat eller et salt deraf, fortrinsvis et farmaceutisk acceptabelt salt deraf, eller en blanding af disse, ifølge et hvilket som helst af kravene 1 til 5 og er farmaceutisk acceptabelt fortyndingsmiddel eller bæremateriale
11. Farmaceutisk præparat, der omfatter: en eller flere forbindelser med generel formel (I) eller en stereoisomer, en tautomer, et N-oxid, et hydrat, et solvat eller et salt deraf, fortrinsvis et farmaceutisk acceptabelt salt deraf, eller en blanding af disse, ifølge et hvilket som helst af kravene 1 til 5; og et eller flere midler, der er udvalgt blandt: et taxan, såsom Docetaxel, Paclitaxel eller Taxol; et epothilon, såsom Ixabepilon, Patupilon eller Sagopilon; Mitoxantron; Predinisolon; Dexamethason; Estramustin; Vinblastin; Vineristin; Doxorubicin; Adriamycin; Idarubicin; Daunorubicin; Bleomycin; Etoposid; Cyclophosphamid; Ifosfamid; Procarbazin; Melphalan; 5-Fluoruracil; Capecitabin; Fludarabin; Cytarabin; Ara-C; 2-Chlor-2'-deoxyadenosin; Thioguanin; et anti-androgen, såsom Flutamid, Cyproteronacetat eller Bicalutamid; Bortezomib; et platinderivat, såsom Cisplatin eller Carboplatin; Chlorambucil; Methotrexate; og Rituximab.
12. Anvendelse af en forbindelse med generel formel (I) eller en stereoisomer, en tautomer, et N-oxid, et hydrat, et solvat eller et salt deraf, fortrinsvis et farmaceutisk acceptabelt salt deraf, eller en blanding af disse, ifølge et hvilket som helst af kravene 1 til 5 til fremstilling af et medikament til profylakse eller behandling af en sygdom.
13. Anvendelse ifølge krav 12, hvor sygdommen er en sygdom med ukontrolleret cellevækst, -proliferation og/eller overlevelse, upassende cellulær immunrespons eller upassende cellulær inflammatorisk respons, fortrinsvis hvor den ukontrollerede cellevækst, -proliferation og/eller overlevelse, den upassende cellulære immunrespons eller den upassende cellulære inflammatoriske respons medieres af Mps-1, mere fortrinsvis hvor sygdommen med ukontrolleret cellevækst, -proliferation og/eller -overlevelse, upassende cellulær immunrespons eller upassende cellulær inflammatorisk respons er en hæmotologisk tumor, en fast tumor og/eller metastaser deraf, f.eks. leukæmier og myelodysplastisk syndrom, maligne lymfomer, hoved- og halstumorer, herunder hjernetumorer og hjernemetastaser, tumorer i thorax, herunder ikke-småcellede og småcellede lungetumorer, gastrointestinale tumorer, endokrine tumorer, brysttumorer og andre gynækologiske tumorer, urologiske tumorer, herunder nyre-, blære- og prostatatumorer, hudtumorer, og sarkomer og/eller metastaser deraf.
14. Forbindelse med generel formel (5):
(5) hvor R1 er en arylgruppe, som er substitueret en eller flere gange, identisk eller forskelligt, med en substituent, der er udvalgt blandt: R6-(Ci-Cg-alkyl)-, R6-(CH2)n(CHOH) (CH2)m-, R6-(CH2) n (CHOH) (CH2)p- 0-, R6- (Ci-C6-alkoxy-Ci-C6-alkyl) -, R6- (Ci-C6-alkoxy-Ci-C6-alkyl) -0-, -C (=0) R 6, -C (=0) 0-R 6, -0C (=0) -R6, -N (H) C (=0) R6, N(R7)C(=0)R6, -N (H) C (=0)NR6R7, -N (R7) C (=0) NRsR7, -nr6r7,-C (=0) N (H) R6, -C(=0)NR6R7, R6-S-, R6-S(=0)-, Rs-S(=0)2-, N (H) S (=0) R6, -N (R7) S (=0) R6, -S (=0) N (H) R6, -S(=0)NR6R7, N (H) S (=0) 2R6, -N (R7) S (=0) 2R6, -S (=0) 2N (H) R6, -S (=0) 2NRsR7, S (=0) (=NR6) R7, -S (=0) (=NR7) R6, -N=S (=0) (R6) R7; og som eventuelt er substitueret en eller flere gange, identisk eller forskelligt, med en substituent, der er udvalgt blandt: halo-, hydroxyl-, cyano-, nitro-, Ci-C6-alkyl-, halo-Ci-C6-alkyl-, Ci-C6~alkoxy-, halo-Ci-C6_alkoxy-, hydroxy-Ci-C6_alkyl-, Ci-C6-alkoxy-Ci-C6-alkyl-, halo-Ci-C6-alkoxy-Ci-C6-alkyl-, R8- (C2-Cg-alkyl)-, R8-(CH2) n (CHOH) (CH2) m-, R8-(Ci-C6-alkoxy)-, R8- (CH2) n (CHOH) (CH2)p-0-, R8-(Ci-C6-alkoxy-Ci-C6-alkyl)-, R8- (C1-C6- alkoxy-Ci-Ce-alkyl)-0-, R8-0-, -C(=0)R8, -C(=0)0-R8, -0C(=0)-R8, -N (H) C (=0) R8, -N (R7) C (=0) R8, -N (H) C (=0) NR8R7, -N (R7) C (=0) NR8R7, -NR8R7 , -C (=0) N (H) R8, -C (=0) NR8R7, R8-S-, R8-S(=0)-, R8-S(=0)2-, -N (H) S (=0) R8, -N (R7) S (=0) R8, -S (=0) N (H) R8, -S(=0)NR8R7, N (H) S (=0) 2R8, -N (R7) S (=0) 2R8, -S (=0) 2N (H) R8, -S (=0) 2NR8R7, S (=0) (=NR8) R7, -S (=0) (=NR7) R8, -N=S (=0) (R8) R7; og R3, R4, R5, R6, R7, R8, n, m og p er som defineret for forbindelsen med generel formel (I) i krav 1, eller en blanding af disse.
15. Forbindelse med generel formel (7):
(7) hvor R2, R3, R4 og R5 er som defineret for forbindelsen med generel formel (I) i et hvilket som helst af kravene 1 til 5, og Rla er en arylgruppe, hvortil er bundet en -NH2-substituent.
16. Anvendelse af en forbindelse med generel formel (5)
(5) hvor R1, RJ, R4, og R5 er som defineret for forbindelsen med generel formel (I) i et hvilket som helst af kravene 1 til 5, til fremstilling af en forbindelse med generel formel (I) ifølge et hvilket som helst af kravene 1 til 5.
17. Anvendelse af en forbindelse med generel formel (7) ifølge krav 15 til fremstilling af en forbindelse med generel formel (I) ifølge et hvilket som helst af kravene 1 til 5.
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EP09075535A EP2343297A1 (en) | 2009-11-30 | 2009-11-30 | Triazolopyridines |
PCT/EP2010/006994 WO2011063908A1 (en) | 2009-11-30 | 2010-11-17 | Triazolopyridines |
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