HRP20230086T1 - Inhibitori lizin specifične demetilaze-1 - Google Patents

Inhibitori lizin specifične demetilaze-1 Download PDF

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HRP20230086T1
HRP20230086T1 HRP20230086TT HRP20230086T HRP20230086T1 HR P20230086 T1 HRP20230086 T1 HR P20230086T1 HR P20230086T T HRP20230086T T HR P20230086TT HR P20230086 T HRP20230086 T HR P20230086T HR P20230086 T1 HRP20230086 T1 HR P20230086T1
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pyrimidin
benzonitrile
aminopiperidin
fluorobenzonitrile
pyridin
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HRP20230086TT
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Young K. Chen
Toufike Kanouni
Stephen W. Kaldor
Jeffrey Alan Stafford
James Marvin Veal
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Celgene Quanticel Research, Inc.
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Publication of HRP20230086T1 publication Critical patent/HRP20230086T1/hr

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Claims (27)

1. Spoj koji ima strukturu sa formulom (III), ili farmaceutski prihvatljiva sol istog, [image] pri čemu, X i Y je svako nezavisno odabrano od C-H, C-F, C-CH3, ili N; Z je odabrano -G, -CH2-G, -CH2-CH2-G, -N(R1)-G, -N(R1)-CH2-G, -O-G, -O-CH2-G, ili -C(O)N(R2)(R3); G je karbociklil, heterociklil ili heteroaril; R1 je vodik ili alkil; R2 i R3 su nezavisno odabrani od vodika, alkila, heterociklila, heterociklilalkila, ili opcionalno, R2 i R3 se spajaju da formiraju N-vezani heterociklil prstenasti sustav; R je odabrano od alkoksi, karbociklilalkiloksi, karbociklila, karbociklilalkila, arila, aralkila, heteroarila, ili heterociklila; i R4 je vodik, halogen, C1-C3 alkil, C1-C3 alkoksi, ili -N(R2)(R3).
2. Spoj iz patentnog zahtjeva 1, ili farmaceutski prihvatljiva sol istog, pri čemu X je odabran iz grupe koja se sastoji od C-H, C-F, C-CH3 i N.
3. Spoj iz patentnih zahtjeva 1-2, ili farmaceutski prihvatljiva sol istog, pri čemu Y je odabran iz grupe koja se sastoji od C-H, C-F, C-CH3 i N.
4. Spoj iz patentnog zahtjeva 1, ili farmaceutski prihvatljiva sol istog, pri čemu X je C-H i Y je C-H.
5. Spoj iz patentnih zahtjeva 1-4, ili farmaceutski prihvatljiva sol istog, pri čemu Z je odabran iz grupe koja se sastoji od -O-CH2-G, -O-G i -N(R1)-CH2-G.
6. Spoj iz patentnih zahtjeva 1-4, ili farmaceutski prihvatljiva sol istog, pri čemu Z je -N(R1)-CH2-G, i R1 je vodik, ili pri čemu Z je -N(R1)-CH2-G, i R1 je alkil.
7. Spoj iz patentnih zahtjeva 1-4, ili farmaceutski prihvatljiva sol istog, pri čemu Z je -N(R1)-G ili Z je -N(R1)-G, i R1 je vodik, ili pri čemu Z je -N(R1)-G, i R1 je alkil.
8. Spoj iz patentnih zahtjeva 1-4, ili farmaceutski prihvatljiva sol istog, pri čemu Z je odabran iz grupe koja se sastoji od -CH2-CH2-G, -CH2-G, i -G.
9. Spoj iz patentnih zahtjeva 1-4, ili farmaceutski prihvatljiva sol istog, pri čemu Z je -C(O)N(R2)(R3).
10. Spoj iz patentnih zahtjeva 1-4, ili farmaceutski prihvatljiva sol istog, pri čemu Z je -C(O)N(R2)(R3), i R2 i R3 su nezavisno odabrani od vodika, ili alkila, ili pri čemu Z je -C(O)N(R2)(R3), i R2 i R3 su nezavisno odabrani od vodika, alkila, ili heterociklila, ili pri čemu Z je -C(O)N(R2)(R3), i R2 i R3 su nezavisno odabrani od vodika, alkila, ili heterociklilalkila, ili pri čemu Z je -C(O)N(R2)(R3), i R2 i R3 se spajaju da bi formirali N-vezani heterociklil prstenasti sustav; ili pri čemu Z je -C(O)N(R2)(R3), R2 i R3 se spajaju da bi formirali N-vezani heterociklil prstenasti sustav, a heterociklil je odabran od opcionalno supstituirane piperdinil, piperizinil, morfolinil, ili pirolidinil grupe, ili pri čemu Z je -C(O)N(R2)(R3), R2 i R3 su oba alkil, i R2 i R3 se spajaju da formiraju N-vezani heterociklil prstenasti sustav.
11. Spoj iz patentnih zahtjeva 1-10, ili farmaceutski prihvatljiva sol istog, pri čemu R4 je odabran iz grupe koja se sastoji od vodika, C1-C3 alkoksi i -N(R2)(R3).
12. Spoj iz patentnih zahtjeva 1-10, ili farmaceutski prihvatljiva sol istog, pri čemu R4 je -N(R2)(R3) i R2 je vodik i R3 je metil, ili pri čemu R4 je -N(R2)(R3) i R2 je vodik i R3 je etil, ili pri čemu R4 je -N(R2)(R3) i R2 je metil i R3 je metil.
13. Spoj iz patentnih zahtjeva 1-12, ili farmaceutski prihvatljiva sol istog, pri čemu G je odabran iz grupe koja se sastoji od heterociklila, heterociklila koji sadrži dušik i heterociklila koji sadrži dušik, pri čemu heterociklil koji sadrži dušik je 5- ili 6-člani heterociklil.
14. Spoj iz patentnih zahtjeva 1-12, ili farmaceutski prihvatljiva sol istog, pri čemu G je heterociklil koji sadrži dušik, a heterociklil je odabran od: [image] [image] [image]
15. Spoj iz patentnih zahtjeva 1-12, ili farmaceutski prihvatljiva sol istog, pri čemu G je heterociklil koji sadrži dušik, a heterociklil je odabran od: [image] [image] [image] ili [image]
16. Spoj iz patentnih zahtjeva 1-12, ili farmaceutski prihvatljiva sol istog, pri čemu G je heterociklil, i heterociklil je odabran od opcionalno supstituirane piperdinil, piperizinil, morfolinil, ili pirolidinil grupe.
17. Spoj iz patentnih zahtjeva 1-16, ili farmaceutski prihvatljiva sol istog, pri čemu R je odabran od alkinila, karbociklilalkinila, heterociklilalkinila, heteroarilalkinila, alkoksi, karbociklilalkiloksi, heteroarila, heterociklila, karbociklila, karbociklilalkila, arila, i aralkila.
18. Spoj iz patentnih zahtjeva 1-16, ili farmaceutski prihvatljiva sol istog, pri čemu R je aril ili heteroaril.
19. Spoj iz patentnih zahtjeva 1-16, ili farmaceutski prihvatljiva sol istog, pri čemu R je aril, i aril grupa je opcionalno supstituirana fenil grupa odabrana od 4-metilfenila, 4-klorofenila, 4-fluorofenila, 4-cijanofenila, 4-(metilsulfonil)fenila, ili 4-trifluorometillfenila.
20. Spoj iz patentnih zahtjeva 1-16, ili farmaceutski prihvatljiva sol istog, pri čemu R je heteroaril, i heteraril grupa je opcionalno supstituirani pirazolil, imidazolil, pirolil, piridinil, pirimidinil, pirazinil, ili piridazinil.
21. Spoj iz patentnih zahtjeva 1-16, ili farmaceutski prihvatljiva sol istog, pri čemu R je biciklični prsten koji sadrži dušik.
22. Spoj iz patentnih zahtjeva 1-16, ili farmaceutski prihvatljiva sol istog, pri čemu R je odabran od: [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] pri čemu R5 je vodik, C1-C6 alkil, ili C1-C6 alkoksi.
23. Spoj iz patentnog zahtjeva 1, pri čemu spoj je odabran od: 4-[5-(4-metilfenil)-2-{[(3S)-pirolidin-3-ilmetil]amino}pirimidin-4-il]benzonitrila; 4-[5-(4-fluorofenil)-2-{[(3S)-pirolidin-3-ilmetil]amino}pirimidin-4-il]benzonitrila; 4-[5-(4-klorofenil)-2-[(3S)-pirolidin-3-ilmetil]aminopirimidin-4-il]benzonitrila; 4-[5-(4-metilfenil)-2-[(3R)-pirolidin-3-ilmetoksi]pirimidin-4-il]benzonitrila; 4-{2-[(3aR,6aS)-oktahidropirolo[3,4-c]pirol-2-il]-5-(4-metilfenil)pirimidin-4-il}benzonitrila; 4-[5-(4-metilfenil)-2-{oktahidro-1H-pirolo[3,4-c]piridin-5-il}pirimidin-4 il]benzonitrila; 4-{2-[(3aR,8aS)-dekahidropirolo[3,4-d]azepin-6-il]-5-(4-metilfenil)pirimidin-4-il}benzonitrila; 4-{2-[(3aR,8aS)-dekahidropirolo[3,4-d]azepin-6-il]-5-(4-fluorofenil)pirimidin-4-il}benzonitrila; 4-(2-{[(3S)-pirolidin-3-ilmetil]amino}-5-[4-(trifluorometil)fenil]pirimidin-4-il)benzonitrila; 4-(2-{[(3aR,5S,6aS)-oktahidrociklopenta[c]pirol-5-il]amino}-5-(4-metilfenil)pirimidin-4-il)benzonitrila; (+)-4-(2-{[(3-fluoropirolidin-3-il)metil]amino}-5-(4-metilfenil)pirimidin-4-il)benzonitrila; (+)-4-[5-(4-metilfenil)-2-[(piperidin-3-il)amino]pirimidin-4-il]benzonitrila; 4-[5-(4-metilfenil)-2-[(piperidin-4-il)amino]pirimidin-4-il]benzonitrila; (+)-4-[5-(4-metilfenil)-2-[(piperidin-3-ilmetil)amino]pirimidin-4-il]benzonitrila; 4-[5-(4-metilfenil)-2-[(piperidin-4-ilmetil)amino]pirimidin-4-il]benzonitrila; (+)-4-[5-(4-metilfenil)-2-[(morfolin-2-ilmetil)amino]pirimidin-4-il]benzonitrila; (+)-4-[5-(4-fluorofenil)-2-[(morfolin-2-ilmetil)amino]pirimidin-4-il]benzonitrila; 4-(2-{2,7-diazaspiro[4.4]nonan-2-il}-5-(4-metilfenil)pirimidin-4-il)benzonitrila; 4-(2-{2,8-diazaspiro[4.5]dekan-2-il}-5-(4-metilfenil)pirimidin-4-il)benzonitrila; 4-[5-(4-metilfenil)-2-{oktahidro-1H-pirolo[3,4-c]piridin-2-il}pirimidin-4-il]benzonitrila; 4-[5-(4-metilfenil)-2-{oktahidro-1H-pirolo[3,2-c]piridin-5-il}pirimidin-4-il]benzonitrila; 4-(2-{2,8-diazaspiro[4.5]dekan-8-il}-5-(4-metilfenil)pirimidin-4-il)benzonitrila; 4-(2-{1,8-diazaspiro[4.5]dekan-8-il}-5-(4-metilfenil)pirimidin-4-il)benzonitrila; 4-[5-(4-metilfenil)-2-{9-oksa-3,7-diazabiciklo[3.3.1]nonan-3-il}pirimidin-4-il]benzonitrila; 4-[5-(4-fluorofenil)-2-{9-oksa-3,7-diazabiciklo[3.3.1]nonan-3-il}pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(2-metilindazol-5-il)pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(1,2,3,3a,4,6,7,7a-oktahidropirolo[3,2-c]piridin-5-il)-5-(4-metilfenil)pirimidin-4-il]benzonitrila; 4-[2-(2,8-diazaspiro[4.5]dekan-8-il)-5-[1-(2,2,2-trifluoroetil)pirazol-4-il]pirimidin-4-il]benzonitrila; 4-[2-(1,2,3,3a,4,6,7,7a-oktahidropirolo[3,2-c]piridin-5-il)-5-[1-(2,2,2-trifluoroetil)pirazol-4-il]pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(1-metilpirazolo[3,4-b]piridin-5-il)pirimidin-4-il]benzonitrila; 4-[2-(2,3,3a,4,5,7,8,8a-oktahidro-1H-pirolo[3,4-d]azepin-6-il)-5-(1-metilpirazolo[3,4-b]piridin-5-il)pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(3-metilimidazo[4,5-b]pyridin-6-il)pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(1-metilpirazolo[4,3-b]piridin-5-il)pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(2-metilpirazolo[4,3-b]piridin-5-il)pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(1-metilpirazolo[3,4-c]piridin-5-il)pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-[1-(oksolan-3-il)pirazol-4-il]pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(1-metilbenzotriazol-5-il)pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(2-metilpirazolo[3,4-c]piridin-5-il)pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(1,2-dimetilbenzimidazol-5-il)pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(2-metilpirazolo[4,3-b]piridin-6-il)pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(1-metilpirolo[3,2-b]piridin-5-il)pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-[1-(oksolan-3-ilmetil)pirazol-4-il]pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-[1-(difluorometil)benzimidazol-5-il]pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-[1-(2,2,2-trifluoroetil)pirazol-4-il]pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-([1,2,4]triazolo[1,5-a]piridin-7-il)pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(4-metilfenil)pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(4-metoksifenil)pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(3-fluoro-4-metoksifenil)pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(2-metilpirazolo[3,4-b]piridin-5-il)pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(2-metilpirazolo[4,3-d]pirimidin-5-il)pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(1-metilbenzimidazol-5-il)pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(1-metilpirazolo[4,3-d]pirimidin-5-il)pirimidin-4-il]benzonitrila; 2-fluoro-4-[2-[4-(metilamino)piperidin-1-il]-5-[1-(2,2,2-trifluoroetil)pirazol-4-il]pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(2-metilpirimidin-5-il)pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(3H-benzimidazol-5-il)pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(2,3-dimetilindazol-5-il)pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(1,3-dimetilindazol-5-il)pirimidin-4-il]-2-fluorobenzonitrila; 4-[5-(3-amino-2-metilindazol-5-il)-2-(4-aminopiperidin-1-il)pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(1-metilbenzotriazol-5-il)pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(4-amino-3-hidroksipiperidin-1-il)-5-(1-metilindazol-5-il)pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(4-amino-3-hidroksipiperidin-1-il)-5-[1-(2,2,2-trifluoroetil)pirazol-4-il]pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(4-amino-3-hidroksipiperidin-1-il)-5-(1-metilindazol-5-il)pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(6-fluoro-1-metilbenzotriazol-5-il)pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(4-amino-3-hidroksipiperidin-1-il)-5-(2-metilindazol-5-il)pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(3-aminopiperidin-1-il)-5-(2-metilindazol-5-il)pirimidin-4-il]-2-fluorobenzonitrila; 2-fluoro-4-[5-(2-metilindazol-5-il)-2-piperazin-1-ilpirimidin-4-il]benzonitrila; 4-[2-(1,4-diazepan-1-il)-5-(2-metilindazol-5-il)pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(4-amino-3-fluoropiperidin-1-il)-5-(1-metilindazol-5-il)pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(4-amino-3-fluoropiperidin-1-il)-5-(2-metilindazol-5-il)pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(2,7-diazaspiro[3. 5]nonan-7-il)-5-(4-metilfenil)pirimidin-4-il]benzonitrila; 4-[2-(2,3,3a,4,5,7,8,8a-oktahidro-1H-pirolo[3,4-d]azepin-6-il)-5-(6-metilpiridin-3-il)pirimidin-4-il]benzonitrila; 4-[2-(1,2,3,3a,4,6,7,7a-oktahidropirolo[3,4-c]piridin-5-il)-5-(1-metilindazol-5-il)pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(l-metilindazol-5-il)pirimidin-4-il]benzonitrila; 4-[2-(2,3,3a,4,5,7,8,8a-oktahidro-1H-pirolo[3,4-d]azepin-6-il)-5-(1H-indazol-6-il)pirimidin-4-il]benzonitrila; 4-[2-(2,3,3a,4,5,7,8,8a-oktahidro-1H-pirolo[3,4-d]azepin-6-il)-5-(1,3-dimetilpirazol-4-il)pirimidin-4-il]benzonitrila; 4-[2-(3,7-diazabiciklo[3.3.1]nonan-3-il)-5-(4-metilfenil)pirimidin-4-il]benzonitrila; 4-[2-(3,7-diazabiciklo[3.3.1]nonan-3-il)-5-(l-metilindazol-5-il)pirimidin-4-il]benzonitrila; 4-[2-(2,8-diazaspiro[4.5]dekan-8-il)-5-[1-(2,2,2-trifluoroetil)pirazol-4-il]pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(1-metilbenzimidazol-5-il)pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(6-metoksipiridin-3-il)pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-[6-(ciklopropilmetoksi)piridin-3-il]pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(6-fluoro-1-metilbenzimidazol-5-il)pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(6,7-difluoro-1-metilbenzimidazol-5-il)pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-([1,2,4]triazolo[1,5-a]piridin-6-il)pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(2-metilindazol-5-il)pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(2-metilindazol-6-il)pirimidin-4-il]benzonitrila; 4-[2-(2,3,3a,4,5,7,8,8a-oktahidro-1H-pirolo[3,4-d]azepin-6-il)-5-(6,7-difluoro-1-metilbenzimidazol-5-il)pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-[6-(2,2,2-trifluoroetoksi)piridin-3-il]pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(6,7-difluoro-1-metilbenzimidazol-5-il)pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(4-aminopiperidin-1-il)-5 -(6-fluoro-1 -metilbenzimidazol-5 -il)pirimidin-4-il] -2-fluorobenzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-[2-(dimetilamino)pirimidin-5-il]pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(2-pirolidin-1-ilpirimidin-5-il)pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(3-metilimidazo[4,5-b]piridin-6-il)pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(2,8-diazaspiro[4.5]dekan-8-il)-5-(3-metilimidazo[4,5-b]piridin-6-il)pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(1,2-dimetilbenzimidazol-5-il)pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(3-metiltriazolo[4,5-b]piridin-6-il)pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-[2-(metilamino)pirimidin-5-il]pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-[2-(ciklopropilamino)pirimidin-5-il]pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-[1-(oksan-4-il)pirazol-4-il]pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(3-aminopirolidin-1-il)-5-(2-metilindazol-5-il)pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(6-amino-3-azabiciklo[3.1.0]heksan-3-il)-5-(2-metilindazol-5-il)pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(1-metilpirazolo[3,4-b]piridin-5-il)pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(2,3,3a,4,5,7,8,8a-oktahidro-1H-pirolo[3,4-d]azepin-6-il)-5-(1,3-benzotiazol-5-il)pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-6-metoksi-5-(2-metil-2H-indazol-5-il)pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(1,4-diazepan-1-il)-6-metoksi-5-(2-metil-2H-indazol-5-il)pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(4-aminoazepan-1-il)-6-metoksi-5-(2-metil-2H-indazol-5-il)pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(4-aminopiperidin-1-il)-6-metoksi-5-(2-metil-2H-indazol-6-il)pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(4-aminopiperidin-1-il)-6-metoksi-5-(1-metil-1H-1,2,3-benzotriazol-5-il)pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(4-aminopiperidin-1-il)-6-metoksi-5-(2-metil-2H-indazol-5-il)pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-6-metoksi-5-[1-(2,2,2-trifluoroetil)-1H-pirazol-4-il]pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-6-metoksi-5-(1-metil-1H-1,2,3-benzotriazol-5-il)pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-[6-(dimetilamino)piridin-3-il]-6-metoksipirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-[2-(dimetilamino)pirimidin-5-il]-6-metoksipirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-6-metoksi-5-{3-metil-3H-[1,2,3]triazolo[4,5-b]piridin-6-il}pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(4-aminopiperidin-1-il)-6-metoksi-5-{3-metil-3H-[1,2,3]triazolo[4,5-b]piridin-6-il}pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-6-metoksi-5-{1-metil-1H-pirazolo[3,4-b]piridin-5-il}pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(2-metil-2H-indazol-5-il)-6-(metilamino)pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(l-metil-1H-indazol-5-il)-6-(metilamino)pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(1,4-diazepan-1-il)-5-(2-metil-2H-indazol-5-il)-6-(metilamino)pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(2-metil-2H-indazol-5-il)-6-(metilamino)pirimidin-4-il]-benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(1-metil-1H-indazol-5-il)-6-(metilamino)pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-(1-metil-1H-1,2,3-benzotriazol-5-il)-6-(metilamino)pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(4-aminopiperidin-1-il)-6-(etilamino)-5-(2-metil-2H-indazol-5-il)pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(4-aminopiperidin-1-il)-6-(metilamino)-5-[1-(2,2,2-trifluoroetil)-1H-pirazol-4-il]pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-[2-(dimetilamino)pirimidin-5-il]-6-(metilamino)pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-[6-(dimetilamino)piridin-3-il]-6-(metilamino)pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-{3-metil-3H-[1,2,3]triazolo[4,5-b]piridin-6-il}-6-(metilamino)pirimidin-4-il]benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-{3-metil-3H-[1,2,3]triazolo[4,5-b]piridin-6-il}-6-(metilamino)pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(1,4-diazepan-1-il)-5-(2-metil-2H-indazol-5-il)-6-(metilamino)pirimidin-4-il]benzonitrila; 4- {2-[4-(dimetilamino)piperidin-1-il]-5-(2-metil-2H-indazol-5-il)-6-(metilamino)pirimidin-4-il}benzonitrila; 4-[2-(4-aminopiperidin-1-il)-6-(metilamino)-5-[1-(2,2,2-trifluoroetil)-1H-pirazol-4-il]pirimidin-4-il]-benzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-{1-metil-1H-pirazolo[3,4-b]pyridin-5-il}-6-(metilamino)pirimidin-4-il]-2-fluorobenzonitrila; 4-[2-(4-aminopiperidin-1-il)-5-{3-metil-3H-[1,2,3]triazolo[4,5-b]piridin-6-il}-6-(metilamino)pirimidin-4-il]benzonitrila; 4-{2-[(3S,4R)-4-amino-3-fluoropiperidin-1-il]-5-(2-metil-2H-indazol-5-il)-6-(metilamino)pirimidin-4-il}benzonitrila; i 4-{2-[(3R,4S)-4-amino-3-fluoropiperidin-1-il]-5-(2-metil-2H-indazol-5-il)-6-(metilamino)pirimidin-4-il}benzonitrila, ili farmaceutski prihvatljiva sol istog.
24. Farmaceutska kompozicija koja sadrži spoj sa formulom (III) kao što je opisano u bilo kojem od patentnih zahtjeva 1-23, ili farmaceutski prihvatljiva sol istog, i farmaceutski prihvatljiv ekscipijens.
25. Spoj sa formulom (III) kao što je opisano u bilo kojem od patentnih zahtjeva 1-23 za primjenu u regulaciji transkripcije gena u stanici.
26. Spoj sa formulom (III) kao što je opisano u bilo kojem od patentnih zahtjeva 1-23, ili farmaceutski prihvatljiva sol istog, za primjenu u liječenju raka.
27. Spoj ili farmaceutski prihvatljiva sol istog za primjenu prema patentnom zahtjevu 26, pri čemu rak je rak prostate, rak dojke, rak mjehura, rak pluća, ili melanom.
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