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HRP20180037T1 - Heterociklični spoj koji sadrži dušik ili njegovu sol - Google Patents

Heterociklični spoj koji sadrži dušik ili njegovu sol Download PDF

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Publication number
HRP20180037T1
HRP20180037T1 HRP20180037TT HRP20180037T HRP20180037T1 HR P20180037 T1 HRP20180037 T1 HR P20180037T1 HR P20180037T T HRP20180037T T HR P20180037TT HR P20180037 T HRP20180037 T HR P20180037T HR P20180037 T1 HRP20180037 T1 HR P20180037T1
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Croatia
Prior art keywords
amino
dimethylamino
pyrimidin
methyl
group
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HRP20180037TT
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English (en)
Inventor
Masaru Takasaki
Toshiaki Tsujino
Shintarou Tanabe
Megumi Ookubo
Kimihiko Sato
Atsushi Hirai
Daisuke Terada
Shinsuke Inuki
Shinsuke Mizumoto
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Fujifilm Corporation
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Publication of HRP20180037T1 publication Critical patent/HRP20180037T1/hr

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    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
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    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
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    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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Claims (14)

1. Spoj predstavljen pomoću opće formule [1]-(1): [image] (u formuli, R2a predstavlja atom vodika ili C1-6alkil grupu koja može biti supstituirana, R4a predstavlja atom vodika ili C1-6alkil grupu koja može biti supstituirana, R17a predstavlja atom vodika ili C1-6alkil grupu koja može biti supstituirana, pod uvjetom da R17a može da formira divalentnu heterocikličnu grupu koja sadrži dušik koja može biti supstituirana zajedno sa R4a, atom dušika za koji se R4a vezuje, i atom ugljika za koji se R17a vezuje, R17b i R18b su isti ili različiti, i predstavljaju atom vodika ili C1-6alkil grupu koja može biti supstituirana, pod uvjetom da R17b i R18b mogu formirati C(=O) zajedno sa atomom ugljika za koji se vezuju, ili R17b i R18b mogu formirati heterocikličnu grupu koja može biti supstituirana zajedno sa atomom ugljika za koji se vezuju, R9a predstavlja C1-6alkil grupu koja može biti supstituirana, C1-6alkoksi grupu koja može biti supstituirana, heterocikličnu grupu koja može biti supstituirana ili N(R15)(R16) (u formuli, R15 predstavlja atom vodika, C1-6alkil grupu koja može biti supstituirana, C2-6alkenil grupu koja može biti supstituirana, C2-6alkinil grupu koja može biti supstituirana ili C3-8cikloalkil grupu koja može biti supstituirana, i R16 predstavlja C1-6alkil grupu koja može biti supstituirana, C2-6alkenil grupu koja može biti supstituirana, C2-6alkinil grupu koja može biti supstituirana, C3-8cikloalkil grupu koja može biti supstituirana, aril grupu koja može biti supstituirana ili heterocikličnu grupu koja može biti supstituirana, ili R15 i R16 mogu formirati cikličnu amino grupu koja može biti supstituirana zajedno sa atomom dušika za koji su vezani), R12a predstavlja C1-6alkil grupu koja može biti supstituirana, aril grupu koja može biti supstituirana ili heterocikličnu grupu koja može biti supstituirana, X2a predstavlja C1-6alkilen grupu koja može biti supstituirana, ili divalentnu alicikličnu ugljikovodičnu grupu koja može biti supstituirana, gdje je divalenta aliciklična ugljikovodična grupa odabrana od 1,2-ciklobutilen, 1,3-ciklobutilen, 1,2-ciklopentilen, 1,3-ciklopentilen, 1,2-cikloheksilen, 1,3-cikloheksilen, 1,4-cikloheksilen, biciklo(3.2.1)oktilen, biciklo(2.2.0)heksilen, i biciklo(5.2.0)nonilen, ili divalentnu aromatičnu ugljikovodičnu grupu koja može biti supstituirana, gdje je divalentna aromatična ugljikovodična grupa odabrana od fenilen, indenilen, naftilen, fluorenilen, fenantrenilen, antrilen, i pirenilen, i X3a predstavlja C2-6alkinilen grupu koja može biti supstituirana ili N(R22)-C(=O) (u formuli, R22 predstavlja atom vodika, C1-6alkil grupu koja može biti supstituirana, C2-6alkenil grupu koja može biti supstituirana, C2-6 alkinil grupu koja može biti supstituirana ili imino zaštitnu grupu koja je odabrana od aril(C1-6alkil) grupe, (C1-6alkoksi)(C1-6alkil) grupe, acil grupe, C1-6alkoksikarbonil grupe, aril(C1-6alkoksi)karbonil grupe, ariloksikarbonil grupe, C1-6alkilsulfonil grupe, arilsulfonil grupe, i silil grupe) ili soli navedenog.
2. Spoj ili njegova sol u skladu sa patentnim zahtjevom 1, gdje R2a je C1-6alkil grupa koja može biti supstituirana, supstituent C1-6alkil grupe koja može biti supstituiran kao R2a je atom halogena, hidroksilna grupa, C1-6 alkilamino grupa koja može biti supstituirana sa jednom ili više grupa koje su odabrane od supstituirane grupe A-3, di(C1-6 alkil)amino grupa koja može biti supstituirana sa jednom ili više grupa koje su odabrane od supstituirane grupe A-3 ili heterociklična grupa koja može biti supstituirana sa jednom ili više grupa koje su odabrane od supstituirane grupe A-3, i supstituirana grupa A-3 koja se sastoji od atoma halogena, hidroksilna grupa koja može biti zaštićena hidroksilnom zaštitnom grupom koja je odabrana od C1-6alkil grupe, C2-6alkenil grupe, aril(C1-6alkil) grupe, (C1-6 alkoksi)(C1-6alkil) grupe, aril(C1-6alkoksi)(C1-6alkil) grupe, acil grupe, C1-6alkoksikarbonil grupe, aril(C1-6 alkoksi)karbonil grupe, C1-6alkilsulfonil grupe, arilsulfonil grupe, silil grupe, tetrahidrofuranil grupe, i tetrahidropiranil grupe, i C1-6alkil grupa koja može biti supstituirana sa hidroksilnom grupom.
3. Spoj ili njegova sol u skladu sa patentnim zahtjevom 1 ili 2, gdje R4a je atom vodika ili C1-6alkil grupa.
4. Spoj ili njegova sol u skladu sa bilo kojim od patentnih zahtjeva 1 do 3, gdje R17a je atom vodika ili C1-6alkil grupa.
5. Spoj ili njegova sol u skladu sa bilo kojim od patentnih zahtjeva 1 do 4, gdje R17b i R18b su isti ili različiti, i predstavljaju C1-6alkil grupu, ili R17b i R18b formiraju C(=O) zajedno sa atomom ugljika za koji se vezuju.
6. Spoj ili njegova sol u skladu sa bilo kojim od patentnih zahtjeva 1 do 5, gdje R9a je N(R15)(R16) (u formuli, R15 predstavlja atom vodika, C1-6alkil grupu koja može biti supstituirana, C2-6alkenil grupu koja može biti supstituirana, C2-6alkinil grupu koja može biti supstituirana ili C3-8cikloalkil grupu koja može biti supstituirana, i R16 predstavlja C1-6alkil grupu koja može biti supstituirana, C2-6alkenil grupu koja može biti supstituirana, C2-6 alkinil grupu koja može biti supstituirana, C3-8cikloalkil grupu koja može biti supstituirana, aril grupu koja može biti supstituirana ili heterocikličnu grupu koja može biti supstituirana, ili R15 i R16 mogu formirati cikličnu amino grupu koja može biti supstituirana zajedno sa atomom dušika za koji se vezuju).
7. Spoj ili njegova sol u skladu sa bilo kojim od patentnih zahtjeva 1 do 6, gdje R12a je aril grupa koja može biti supstituirana.
8. Spoj ili njegova sol u skladu sa bilo kojim od patentnih zahtjeva 1 do 7, gdje X2a je C1-6alkilen grupa koja može biti supstituirana ili divalentna aliciklična ugljikovodična grupa koja može biti supstituirana.
9. Spoj ili njegova sol u skladu sa bilo kojim od patentnih zahtjeva 1 do 8, gdje X3a je C2-6alkinilen grupa koja može biti supstituirana, poželjno etinilen grupa.
10. Spoj ili njegova sol u skladu sa patentnim zahtjevom 1, koji je spoj odabran od (S,E)-N-(3-(2-(4-(dimetilamino)-N-metil-2-butenamido)propanamido)fenil)-4-(propilamino)-2-((2-(piridin-4-il)etil)amino)pirimidin-5-karboksamid, (S,E)-2-((4-karbamoilfenil)amino)-N-(3-(2-(4-(dimetilamino)-N-metil-2-butenamido)propanamido)fenil)-4-(propilamino)pirimidin-5-karboksamid, (E)-2-((4-karbamoilfenil)amino)-N-(3-(2-(4-(dimetilamino)-N-metil-2-butenamido)actamido)cikloheksil)-4-(propilamino)pirimidin-5-karboksamid, (S,E)-2-((4-karbamoilfenil)amino)-N-(3-(2-(4-(dietilamino)-N-metil-2-butenamido)propanamido)fenil)-4-(propilamino)pirimidin-5-karboksamid, (S,E)-2-((4-karbamoilfenil)amino)-N-(3-(2-(4-(dimetilamino)-N-metil-2-butenamido)propanamido)propil)-4-(propilamino)pirimidin-5-karboksamid, (S,E)-N-(3-(2-(4-(dimetilamino)-N-metil-2-butenamido)propanamido)fenil)-2-(izohinolin-6-ilamino)-4-(propilamino)pirimidin-5-karboksamid, (S,E)-2-(cinolin-6-ilamino)-N-(3-(2-(4-(dimetilamino)-N-metil-2-butenamido)propanamido)fenil)-4-(propilamino)pirimidin-5-karboksamid, (S,E)-4-(dimetilamino)-N-(1-((5-(2-((3-fluorofenil)amino)-4-(propilamino)pirimidin-5-il)-4-pentin-1-il)amino)-1-oksopropan-2-il)-N-metil-2-butenamid, (S,E)-N-(1-((5-(2-((3-cijanofenil)amino)-4-(propilamino)pirimidin-5-il)-4-pentin-1-il)amino)-1-oksopropan-2-il)-4-(dimetilamino)-N-metil-2-butenamid, (S,E)-4-((5-(5-(2-(4-(dimetilamino)-N-metil-2-butenamido)propanamido)-1-pentin-1-il)-4-(propilamino)pirimidin-2-il)amino)benzamid, (S,E)-N-(1-((5-(2-((4-cijanofenil)amino)-4-(propilamino)pirimidin-5-il)-4-pentin-1-il)amino)-1-oksopropan-2-il)-4-(dimetilamino)-N-metil-2-butenamid, (E)-4-(dimetilamino)-N-(2-((5-(2-((4-fluorofenil)amino)-4-(propilamino)pirimidin-5-il)-4-pentin-1-il)amino)-2-oksoetil)-N-metil-2-butenamid, (E)-N-(2-((5-(2-((4-cijanofenil)amino)-4-(propilamino)pirimidin-5-il)-4-pentin-1-il)amino)-2-oksoetil)-4-(dimetilamino)-N-metil-2-butenamid, (S,E)-4-(dimetilamino)-N-(1-((5-(2-((3-fluorofenil)amino)-4-(propilamino)pirimidin-5-il)-4-pentin-1-il)amino)-1-oksobutan-2-il)-N-metil-2-butenamid, (S,E)-4-(dimetilamino)-N-(1-((5-(2-((3-fluoro-4-metoksifenil)amino)-4-(propilamino)pirimidin-5-il)-4-pentin-1-il)amino)-1-oksopropan-2-il)-N-metil-2-butenamid, (S,E)-4-(dimetilamino)-N-(1-((5-(2-((6-fluoropiridin-3-il)amino)-4-(propilamino)pirimidin-5-il)-4-pentin-1-il)amino)-1-oksopropan-2-il)-N-metil-2-butenamid, (S,E)-4-(dimetilamino)-N-(1-((5-(2-((6-fluoropiridin-3-il)amino)-4-((4-metoksifenil)amino)pirimidin-5-il)-4-pentin-1-il)amino)-1-oksopropan-2-il)-N-metil-2-butenamid, (E)-4-(dimetilamino)-N-(2-((5-(2-((3-fluorofenil)amino)-4-(propilamino)pirimidin-5-il)-4-pentin-1-il)amino)-2-oksoetil)-N-metil-2-butenamid, (S,E)-N-(5-(2-((4-cijanofenil)amino)-4-(propilamino)pirimidin-5-il)-4-pentin-1-il)-1-(4-(dimetilamino)-2-butenoil)pirolidin-2-karboksamid, (S,E)-N-(1-((5-(4-(ciklopropilamino)-2-((3-fluoro-4-metoksifenil)amino)pirimidin-5-il)-4-pentin-1-il)amino)-1-oksopropan-2-il)-4-(dimetilamino)-N-metil-2-butenamid, (S,E)-4-(dimetilamino)-N-(1-((5-(2-((3-fluoro-4-metoksifenil)amino)-4-((3-fluoropropil)amino)pirimidin-5-il)-4-pentin-1-il)amino)-1-oksopropan-2-il)-N-metil-2-butenamid, (S,E)-N-(1-((5-(2-((4-cijanofenil)amino)-4-(propilamino)pirimidin-5-il)-4-pentin-1-il)amino)-3-hidroksi-1-oksopropan-2-il)-4-(dimetilamino)-N-metil-2-butenamid, (2S,4R)-1-((E)-4-(dimetilamino)-2-butenoil)-N-(5-(2-((3-fluorofenil)amino)-4-(propilamino)pirimidin-5-il)-4-pentin-1-il)-4-hidroksipirolidin-2-karboksamid, (2S,4S)-1-((E)-4-(dimetilamino)-2-butenoil)-4-fluoro-N-(5-(2-((3-fluorofenil)amino)-4-(metilamino)pirimidin-5-il)-4-pentin-1-il)pirolidin-2-karboksamid, (2S,4S)-1-((E)-4-(dimetilamino)-2-butenoil)-N-(5-(2-((3-fluorofenil)amino)-4-(metilamino)pirimidin-5-il)-4-pentin-1-il)-4-metoksipirolidin-2-karboksamid, (2S,4S)-1-((E)-4-(dimetilamino)-2-butenoil)-4-fluoro-N-(5-(2-((4-fluorofenil)amino)-4-(metilamino)pirimidin-5-il)-4-pentin-1-il)pirolidin-2-karboksamid, (2S,4R)-1-((E)-4-(dimetilamino)-2-butenoil)-4-fluoro-N-(5-(2-((4-fluorofenil)amino)-4-(metilamino)pirimidin-5-il)-4-pentin-1-il)pirolidin-2-karboksamid, (2S,4S)-1-((E)-4-(dimetilamino)-2-butenoil)-N-(5-(2-((4-fluorofenil)amino)-4-(metilamino)pirimidin-5-il)-4-pentin-1-il)-4-metoksipirolidin-2-karboksamid, (2S,4R)-1-((E)-4-(dimetilamino)-2-butenoil)-N-(5-(2-((4-fluorofenil)amino)-4-(metilamino)pirimidin-5-il)-4-pentin-1-il)-4-metoksipirolidin-2-karboksamid, (S,E)-1-(4-(dimetilamino)-2-butenoil)-N-(5-(2-((4-fluorofenil)amino)-4-(metilamino)pirimidin-5-il)-4-pentin-1-il)azetidin-2-karboksamid, (2S,4S)-N-(5-(2-((4-cijanofenil)amino)-4-(metilamino)pirimidin-5-il)-4-pentin-1-il)-1-((E)-4-(dimetilamino)-2-butenoil)-4-fluoropirolidin-2-karboksamid, (E)-N-(2-((5-(2-((4-cijanofenil)amino)-4-(metilamino)pirimidin-5-il)-4-pentin-1-il)amino)-2-oksoetil)-4-(dimetilamino)-N-metil-2-butenamid, (S,E)-4-(dimetilamino)-N-(1-((3-((2-((3-fluorofenil)amino)-4-(propilamino)pirimidin-5-il)etinil)fenil)amino)-1-oksopropan-2-il)-N-metil-2-butenamid, (S,E)-4-((5-((3-(2-(4-(dimetilamino)-N-metil-2-butenamido)propanamido)fenil)etinil)-4-(propilamino)pirimidin-2-il)amino)benzamid, (S,E)-N-(1-((5-(2-((4-cijanofenil)amino)-4-(pirolidin-1-il)pirimidin-5-il)-4-pentin-1-il)amino)-1-oksopropan-2-il)-4-(dimetilamino)-N-metil-2-butenamid, (S,E)-4-(dimetilamino)-N-(1-((5-(2-((2-fluoropiridin-4-il)amino)-4-(pirolidin-1-il)pirimidin-5-il)-4-pentin-1-il)amino)-1-oksopropan-2-il)-N-metil-2-butenamid, (S,E)-4-(dimetilamino)-N-(1-((5-(2-((2-fluoropiridin-4-il)amino)-4-(propilamino)pirimidin-5-il)-4-pentin-1-il)amino)-1-oksopropan-2-il)-N-metil-2-butenamid, (S,E)-N-(1-((5-(4-(ciklopropilamino)-2-((2-fluoropiridin-4-il)amino)pirimidin-5-il)-4-pentin-1-il)amino)-1-oksopropan-2-il)-4-(dimetilamino)-N-metil-2-butenamid, (S,E)-4-(dimetilamino)-N-metil-N-(1-((5-(2-((3-metilizotiazol-5-il)amino)-4-(propilamino)pirimidin-5-il)-4-pentin-1-il)amino)-1-oksopropan-2-il)-2-butenamid, (S,E)-4-(dimetilamino)-N-(1-((5-(4-((3-metoksipropil)amino)-2-((2-metoksipiridin-4-il)amino)pirimidin-5-il)-4-pentin-1-il)amino)-1-oksopropan-2-il)-N-metil-2-butenamid, (S,E)-1-(4-(dimetilamino)-2-butenoil)-N-(5-(4-((3-metoksipropil)amino)-2-((metoksipiridin-4-il)amino)pirimidin-5-il)-4-pentin-1-il)pirolidin-2-karboksamid, (2S,4S)-1-((E)-4-(dimetilamino)-2-butenoil)-4-fluoro-N-(5-(4-((3-metoksipropil)amino)-2-((metoksipiridin-4-il)amino)pirimidin-5-il)-4-pentin-1-il)pirolidin-2-karboksamid, (S,E)-1-(4-(dimetilamino)-2-butenoil)-N-(5-(2-((2-metoksipiridin-4-il)amino)-4-(propilamino)pirimidin-5-il)-4-pentin-1-il)pirolidin-2-karboksamid, (2S,4S)-1-((E)-4-(dimetilamino)-2-butenoil)-4-fluoro-N-(5-(2-((2-metoksipiridin-4-il)amino)-4-(propilamino)pirimidin-5-il)-4-pentin-1-il)pirolidin-2-karboksamid, (E)-4-(dimetilamino)-N-(2-((5-(2-((2-metoksipiridin-4-il)amino)-4-(propilamino)pirimidin-5-il)-4-pentin-1-il)amino)-2-oksoetil)-N-metil-2-butenamid, (S,E)-4-(dimetilamino)-N-(1-((5-(2-((3-fluorofenil)amino)-4-((4-metoksifenil)amino)pirimidin-5-il)-4-pentin-1-il)amino)-1-oksopropan-2-il)-N-metil-2-butenamid, (S,E)-4-(dimetilamino)-N-(1-((5-(2-((3-fluorofenil)amino)-4-morfolinopirimidin-5-il)-4-pentin-1-il)amino)-1-oksopropan-2-il)-N-metil-2-butenamid, (E)-4-(dimetilamino)-N-(2-((5-(2-((4-fluorofenil)amino)-4-((3-fluoropropil)amino)pirimidin-5-il)-4-pentin-1-il)amino)-2-oksoetil)-N-metil-2-butenamid, (S,E)-N-(1-((5-(2-((4-cijanofenil)amino)-4-(ciklopropilamino)pirimidin-5-il)-4-pentin-1-il)amino)-1-oksopropan-2-il)-4-(dimetilamino))-N-metil-2-butenamid, (S,E)-N-(1-((5-(2-((4-cijanofenil)amino)-4-((3-fluoropropil)amino)pirimidin-5-il)-4-pentin-1-il)amino)-1-oksopropan-2-il)-4-(dimetilamino))-N-metil-2-butenamid, (S,E)-4-(dimetilamino))-N-(1-((5-(4-(etilamino)-2-((1-metil-1H-indazol-5-il)amino)pirimidin-5-il)-4-pentin-1-il)amino)-1-oksopropan-2-il)-N-metil-2-butenamid, (S,E)-N-(1-((5-(4-(ciklopropilamino)-2-((1-metil-1H-indazol-5-il)amino)pirimidin-5-il)-4-pentin-1-il)amino)-1-oksopropan-2-il)-4-(dimetilamino))-N-metil-2-butenamid, (S,E)-4-(dimetilamino))-N-metil-N-(1-((5-(2-((1-metil-1H-indazol-5-il)amino)-4-(metilamino)pirimidin-5-il)-4-pentin-1-il)amino)-1-oksopropan-2-il)-2-butenamid, (S,E)-N-(5-(2-((1H-indazol-5-il)amino)-4-(metilamino)pirimidin-5-il)-4-pentin-1-il)-1-(4-(dimetilamino)-2-butenoil)pirolidin-2-karboksamid, (S,E)-N-(5-(2-((1H-indazol-5-il)amino)-4-(etilamino)pirimidin-5-il)-4-pentin-1-il)-1-(4-(dimetilamino)-2-butenoil)pirolidin-2-karboksamid, (S,E)-N-(5-(2-((1H-indazol-5-il)amino)-4-((3-metoksipropil)amino)pirimidin-5-il)-4-pentin-1-il)-1-(4-(dimetilamino)-2-butenoil)pirolidin-2-karboksamid, (E)-4-(dimetilamino)-N-((S)-1-(((1S,3R)-3-((2-((3-fluorofenil)amino)-4-(propilamino)pirimidin-5-il)etinil)cikloheksil)amino)-1-oksopropan-2-il)-N-metil-2-butenamid, (E)-4-(dimetilamino)-N-((S)-1-(((1S,3R)-3-((2-((3-fluorofenil)amino)-4-(propilamino)pirimidin-5-il)etinil)ciklobutil)amino)-1-oksopropan-2-il)-N-metil-2-butenamid, (E)-N-((S)-1-(((1S,3R)-3-((2-((4-cijanofenil)amino)-4-(metilamino)pirimidin-5-il)etinil)ciklobutil)amino)-1-oksopropan-2-il)-4-(dimetilamino)-N-metil-2-butenamid, (E)-4-(dimetilamino)-N-((S)-1-(((1S,3R)-3-((2-((3-fluorofenil)amino)-4-(metilamino)pirimidin-5-il)etinil)ciklobutil)amino)-1-oksopropan-2-il)-N-metil-2-butenamid, (E)-N-((S)-1-(((1S,3R)-3-((2-((4-cijanofenil)amino)-4-(metilamino)pirimidin-5-il)etinil)ciklobutil)amino)-1-oksopropan-2-il)-4-(dimetilamino)-N-metil-2-butenamid, (E)-N-((S)-1-(((1S,3R)-3-((2-((3-cijanofenil)amino)-4-(metilamino)pirimidin-5-il)etinil)ciklobutil)amino)-1-oksopropan-2-il)-4-(dimetilamino)-N-metil-2-butenamid, (E)-4-(dimetilamino)-N-((S)-1-(((1S,3R)-3-((2-((3-fluoro-4-metoksifenil)amino)-4-(metilamino)pirimidin-5-il)etinil)ciklobutil)amino)-1-oksopropan-2-il)-N-metil-2-butenamid, (E)-4-(dimetilamino)-N-((S)-1-(((1S,3R)-3-((2-((4-fluorofenil)amino)-4-(metilamino)pirimidin-5-il)etinil)ciklobutil)amino)-1-oksopropan-2-il)-N-metil-2-butenamid, (E)-N-((S)-1-(((1S,3R)-3-((2-((3-cijanofenil)amino)-4-(ciklopropilamino)pirimidin-5-il)etinil)ciklobutil)amino)-1-oksopropan-2-il)-4-(dimetilamino)-N-metil-2-butenamid, (E)-4-(dimetilamino)-N-((S)-1-(((1S*,3R*)-3-((2-((2-fluoropiridin-4-il)amino)-4-(propilamino)pirimidin-5-il)etinil)ciklobutil)amino)-1-oksopropan-2-il)-N-metil-2-butenamid, (E)-4-(dimetilamino)-N-((S)-1-(((1S,3R)-3-((2-((2-metoksipiridin-4-il)amino)-4-(propilamino)pirimidin-5-il)etinil)ciklobutil)amino)-1-oksopropan-2-il)-N-metil-2-butenamid, (E)-N-((S)-1-(((1S,3R)-3-((2-((4-cijanofenil)amino)-4-(metilamino)pirimidin-5-il)etinil)cikloheksil)amino)-1-oksopropan-2-il)-4-(dimetilamino)-N-metil-2-butenamid, (E)-N-((S)-1-(((1S*,3R*)-3-((2-((4-cijanofenil)amino)-4-(ciklopropilamino)pirimidin-5-il)etinil)ciklobutil)amino)-1-oksopropan-2-il)-4-(dimetilamino)-N-metil-2-butenamid, (E)-N-((S)-1-(((1S*,3R*)-3-((4-(ciklopropilamino)-2-((4-fluorofenil)amino)pirimidin-5-il)etinil)ciklobutil)amino)-1-oksopropan-2-il)-4-(dimetilamino)-N-metil-2-butenamid, (E)-N-((S)-1-(((1S*,3R*)-3-((4-(ciklopropilamino)-2-((3-fluoro-4-metoksifenil)amino)pirimidin-5-il)etinil)ciklobutil)amino)-1-oksopropan-2-il)-4-(dimetilamino)-N-metil-2-butenamid, (E)-4-(dimetilamino)-N-((S)-1-(((1S,3R)-3-((2-((3-fluorofenil)amino)-4-((3-fluoropropil)amino)pirimidin-5-il)etinil)ciklobutil)amino)-1-oksopropan-2-il)-N-metil-2-butenamid, (E)-N-((S)-1-(((1S,3R)-3-((2-((4-cijanofenil)amino)-4-((3-fluoropropil)amino)pirimidin-5-il)etinil)ciklobutil)amino)-1-oksopropan-2-il)-4-(dimetilamino)-N-metil-2-butenamid, (E)-4-(dimetilamino)-N-((S)-1-(((1S,3R)-3-((2-((3-fluorofenil)amino)-4-((3-metoksipropil)amino)pirimidin-5-il)etinil)ciklobutil)amino)-1-oksopropan-2-il)-N-metil-2-butenamid, (E)-N-((S)-1-(((1S,3R)-3-((2-((4-cijanofenil)amino)-4-((3-metoksipropil)amino)pirimidin-5-il)etinil)ciklobutil)amino)-1-oksopropan-2-il)-4-(dimetilamino)-N-metil-2-butenamid, (E)-4-(dimetilamino)-N-((S)-1-(((1S,3R)-3-((2-((3-fluoro-4-metoksifenil)amino)-4-(metilamino)pirimidin-5-il)etinil)cikloheksil)amino)-1-oksopropan-2-il)-N-metil-2-butenamid, (S,E)-4-(dimetilamino)-N-metil-N-(1-((5-(2-((2-metilpiridin-4-il)amino)-4-(propilamino)pirimidin-5-il)-4-pentin-1-il)amino)-1-oksopropan-2-il)-2-butenamid, (S,E)-N-(1-((5-(2-(benzo[d]tiazol-6-ilamino)-4-(propilamino)pirimidin-5-il)-4-pentin-1-il)amino)-1-oksopropan-2-il)-4-(dimetilamino)-N-metil-2-butenamid, (S,E)-1-(4-(dimetilamino)-2-butenoil)-N-(5-(2-((1-metil-1H-indazol-5-il)amino)-4-(propilamino)pirimidin-5-il)-4-pentin-1-il)pirolidin-2-karboksamid, (S,E)-1-(4-(dimetilamino)-2-butenoil)-N-(5-(2-((1-metil-1H-pirazolo[3,4-b]piridin-5-il)amino)-4-(propilamino)pirimidin-5-il)-4-pentin-1-il)pirolidin-2-karboksamid, (S,E)-1-(4-(dimetilamino)-2-butenoil)-N-(5-(2-((1-(2-metoksietil)-1H-pirazolo[3,4-b]piridin-5-il)amino)-4-(propilamino)pirimidin-5-il)-4-pentin-1-il)pirolidin-2-karboksamid, (S,E)-4-(dimetilamino)-N-metil-N-(1-((5-(2-((3-metil-1H-pirazolo[3,4-b]piridin-5-il)amino)-4-(propilamino)pirimidin-5-il)-4-pentin-1-il)amino)-1-oksopropan-2-il)-2-butenamid, (S,E)-1-(4-(dimetilamino)-2-butenoil)-N-(5-(2-((3-metil-1H-pirazolo[3,4-b]piridin-5-il)amino)-4-(propilamino)pirimidin-5-il)-4-pentin-1-il)pirolidin-2-karboksamid, i (S,E)-1-(4-(dimetilamino)-2-butenoil)-N-(5-(2-((3-metoksi-1H-pirazolo[3,4-b]piridin-5-il)amino)-4-(propilamino)pirimidin-5-il)-4-pentin-1-il)pirolidin-2-karboksamid.
11. Farmaceutska kompozicija koja sadrži spoj ili njegovu sol u skladu sa bilo kojim od patentnih zahtjeva 1 do 10.
12. Spoj ili njegova sol u skladu sa bilo kojim od patentnih zahtjeva 1 do 10 ili farmaceutska kompozicija u skladu sa patentnim zahtjevom 11 za primjenu u liječenju bolesti ili stanja koje je povezano sa FLT3.
13. Spoj ili njegova sol u skladu sa bilo kojim od patentnih zahtjeva 1 do 10 ili farmaceutska kompozicija u skladu sa patentnim zahtjevom 11 za primjenu u liječenju akutne mijeloidne leukemije.
14. Spoj ili njegova sol u skladu sa bilo kojim od patentnih zahtjeva 1 do 10 ili farmaceutska kompozicija u skladu sa patentnim zahtjevom 11 za primjenu kao FLT3 inhibitor.
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