HRP20110908T1 - Hidroksilirani i metoksilirani ciklopenta [d] pirimidini kao inhibitori kinaze akt proteina - Google Patents

Hidroksilirani i metoksilirani ciklopenta [d] pirimidini kao inhibitori kinaze akt proteina Download PDF

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HRP20110908T1
HRP20110908T1 HR20110908T HRP20110908T HRP20110908T1 HR P20110908 T1 HRP20110908 T1 HR P20110908T1 HR 20110908 T HR20110908 T HR 20110908T HR P20110908 T HRP20110908 T HR P20110908T HR P20110908 T1 HRP20110908 T1 HR P20110908T1
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Croatia
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methyl
piperazin
hydroxy
cyclopenta
dihydro
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HR20110908T
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S. Mitchell Ian
F. Blake James
Xu Rui
C. Kallan Nicholas
Xiao Dengming
Lee Spencer Keith
R. Bencsik Josef
Liang Jun
Safina Brian
Zhang Birong
Chabot Christine
Do Steven
W. Wallace Eli
L. Banka Anna
T. Schlachter Stephen
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Array Biopharma
Genentech
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Application filed by Array Biopharma, Genentech filed Critical Array Biopharma
Publication of HRP20110908T1 publication Critical patent/HRP20110908T1/hr

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Abstract

Spoj, naznačen time, da ima formulu I: i rastvoreni enantiomeri, rastvoreni dijastereomeri i njegove soli, gdje: R1 je Me; R2 je H; R5 je H; A je,G je fenil opcijski supstituiran jednom do četiri R9 skupine ili 5-6-člani heteroaril opcijski supstituiran halogenom; R6 i R7 su neovisno H, OCH3, (C3-C6 cikloalkil)-(CH2), (C3-C6 cikloalkil)-(CH2CH2), V-(CH2)0-1 gdje V je 5-6-člani heteroaril, W-(CH2))1-2 gdje W je fenil opcijski supstituiran s F, Cl, Br, I, OMe, CF3 ili Me, C3-C6-cikloalkil opcijski supstituiran s C1-C3alkil ili O(C1-C3alkil), hidroksi-(C3-C6-cikloalkil), fluoro-(C3-C6-cikloalkil), CH(CH3)CH(OH)fenil, 4-6-člani heterocikl opcijski supstituiran sljedećima F, OH, C1-C3 alkil, ciklopropilmetil ili C(=O)(C1-C3 alkil), ili C1-C6-alkil opcijski supstituiran s jednom ili više skupina neovisno odabranih od sljedećih OH, okso, O(C1-C6-alkil), CN, F, NH2, NH(C1-C6-alkil), N (C1-C6-alkil)2, ciklopropil, fenil, imidazolil, piperidinil, pirolidinil, morfolinil, tetrahidrofuranil, oksetanil ili tetrahidropiranil, ili R6 i R7 zajedno s dušikom na koji su priključeni tvore 4-7-člani heterociklički prsten opcijski supstituiran s jednom ili više skupina neovisno odabranih od sljedećih OH, halogen, okso, CF3, CH2CF3, CH2CH2OH, O(C1-C3 alkil), C(=O)CH3, NH2, NHMe, N(Me)2, S(O)2CH3, ciklopropilmetil i C1-C3 alkil; Rc i Rd su H, R8 je H; svaki R9 je neovisno halogen, C1-C6-alkil, C3-C6-cikloalkil, O-(C1-C6-alkil), CF3, OCF3, S(C1-C6-alkil), CN,OCH2-fenil, CH2O-fenil, NH2, NH-(C1-C6-alkil), N-(C1-C6-alkil)2, piperidin, pirolidin, CH2F, CHF2, OCH2F, OCHF2, OH, SO2(C1-C6-alkil), C(O)NH2, C(O)NH(C1-C6-alkil) i C(O)N(C1-C6-alkil)2;R10 je H. Patent sadrži još 16 patentnih zahtjeva.

Claims (17)

1. Spoj, naznačen time, da ima formulu I: [image] i rastvoreni enantiomeri, rastvoreni dijastereomeri i njegove soli, gdje: R1 je Me; R2 je H; R5 je H; A je [image] , G je fenil opcijski supstituiran jednom do četiri R9 skupine ili 5-6-člani heteroaril opcijski supstituiran halogenom; R6 i R7 su neovisno H, OCH3, (C3-C6 cikloalkil)-(CH2), (C3-C6 cikloalkil)-(CH2CH2), V-(CH2)0-1gdje V je 5-6-člani heteroaril, W-(CH2))1-2 gdje W je fenil opcijski supstituiran s F, Cl, Br, I, OMe, CF3ili Me, C3-C6-cikloalkil opcijski supstituiran s C1-C3alkil ili O(C1-C3alkil), hidroksi-(C3-C6-cikloalkil), fluoro-(C3-C6-cikloalkil), CH(CH3)CH(OH)fenil, 4-6-člani heterocikl opcijski supstituiran sljedećima F, OH, C1-C3 alkil, ciklopropilmetil ili C(=O)(C1-C3 alkil), ili C1-C6-alkil opcijski supstituiran s jednom ili više skupina neovisno odabranih od sljedećih OH, okso, O(C1-C6-alkil), CN, F, NH2, NH(C1-C6-alkil), N (C1-C6-alkil)2, ciklopropil, fenil, imidazolil, piperidinil, pirolidinil, morfolinil, tetrahidrofuranil, oksetanil ili tetrahidropiranil, ili R6 i R7 zajedno s dušikom na koji su priključeni tvore 4-7-člani heterociklički prsten opcijski supstituiran s jednom ili više skupina neovisno odabranih od sljedećih OH, halogen, okso, CF3, CH2CF3, CH2CH2OH, O(C1-C3 alkil), C(=O)CH3, NH2, NHMe, N(Me)2, S(O)2CH3, ciklopropilmetil i C1-C3 alkil; Rc i Rd su H, R8 je H; svaki R9 je neovisno halogen, C1-C6-alkil, C3-C6-cikloalkil, O-(C1-C6-alkil), CF3, OCF3, S(C1-C6-alkil), CN,OCH2-fenil, CH2O-fenil, NH2, NH-(C1-C6-alkil), N-(C1-C6-alkil)2, piperidin, pirolidin, CH2F, CHF2, OCH2F, OCHF2, OH, SO2(C1-C6-alkil), C(O)NH2, C(O)NH(C1-C6-alkil) i C(O)N(C1-C6-alkil)2; R10 je H.
2. Spoj prema zahtjevu 1, naznačen time, da ima formulu IB: [image]
3. Spoj prema zahtjevu 1 ili 2, naznačen time, da G je fenil opcijski supstituiran s jednom ili više skupina neovisno odabranih od sljedećih F, Cl, Br, I, Me, etil, izopropil, CN, CF3, OCF3, SMe, OMe i OCH2Ph.
4. Spoj prema bilo kojem od zahtjeva 1 do 3, naznačen time, da G je fenil, 2-klorofenil, 3-klorofenil, 4-klorofenil, 4-fluorofenil, 4-bromofenil, 4-metilfenil, 4-etilfenil, 4-izopropilfenil, 4-trifluorometilfenil, 4-cijanofenil, 4-metoksifenil, 4-etoksifenil, 4-tiometilfenil, 4-trifluorometoksifenil, 4-ciklopropilfenil, 4-kloro-3-fluorofenil, 3,4-difluorofenil, 4-bromo-3-fluorofenil, 3-fluoro-4-metilfenil, 3-fluoro-4-metoksi-fenil, 3-fluoro-4-bromofenil, 3-fluoro-4-trifluorometilfenil, 4-cijano-3-fluorofenil, 3,4-diklorofenil, 2,4-diklorofenil, 2,4-difluorofenil, 2-kloro-4-fluorofenil, 2-fluoro-4-klorofenil, 3,5-diklorofenil, 3,5-difluorofenil, 3-kloro-5-fluorofenil, 3-kloro-4-fluorofenil, 3-bromo-4-fluorofenil, 3,5-difluoro-4-klorofenil, 2,3-difluoro-4-klorofenil, 2,5-difluoro-4-klorofenil, 3,5-difluoro-4-bromofenil, 2,3-difluoro-4-bromofenil, 2,5-difluoro-4-bromofenil ili 4-(OCH2Ph)-fenil.
5. Spoj prema bilo kojem od zahtjeva 1 do 4, naznačen time, da G je 4-klorofenil, 2,4-diklorofenil, 3-kloro-4-fluorofenil, 3,4-difluorofenil, 4-kloro-3-fluorofenil, 3-fluoro-4-bromofenil, 3,4-diklorofenil, 4-metoksifenil, 4-fluorofenil, 4-bromofenil, 4-cijanofenil, 4-trifluorometilfenil, 4-tiometilfenil ili 4-metilfenil.
6. Spoj prema zahtjevu 1, naznačen time, da G je tiofen ili piridin opcijski supstituiran halogenom.
7. Spoj prema bilo kojem od zahtjeva 1 do 6, naznačen time, da je G odabran od sljedećih struktura: [image]
8. Spoj prema bilo kojem od zahtjeva 1 do 7, naznačen time, da su R6 i R7 neovisno odabrani od sljedećih H, OCH3, (C3-C6 cikloalkil)-(CH2), (C3-C6 cikloalkil)-(CH2CH2), V-(CH2)0-1gdje V je 5-6-člani heteroaril koji ima od jedan do dva heteroatoma u prstenu neovisno odabranih od sljedećih N, O i S, W-(CH2)1-2gdje W je fenil opcijski supstituiran s F, Cl ili Me, C3-C6-cikloalkil opcijski supstituiran s OCH3, hidroksi-(C3-C6-cikloalkil), fluoro-(C3-C6-cikloalkil), CH(CH3)CH(OH)fenil, 5-6-člani heterocikl opcijski supstituiran s CH3 ili C(=O)CH3, ili C1-C6-alkil opcijski supstituiran s jednom ili više skupina neovisno odabranih od sljedećih OH, okso, O(C1-C6-alkil), CN, F, NH2, NH(C1-C6-alkil), N(C1-C6-alkil)2, fenil, imidazolil, piperidinil, pirolidinil, morfolinil i tetrahidropiranil.
9. Spoj prema bilo kojem od zahtjeva 1 do 8, naznačen time, da su R6 i R7 neovisno odabrani od sljedećih H, metil, etil, izopropil, izobutil, tert-butil, 3-pentil, OCH3, CH2CH2OH, CH2CH2OMe, CH2CH2CF3, CH2CH(CH3)OH, CH2CH(CF3)OH, CH2CF3, CH2CH2F, CH2C(=O)NH2, CH2C(=O)NH(CH3), CH2C(=O)N(CH3)2, CH2C(=O)NH(iPr), CH2CH2C(=O)NH2, CH2-ciklopropil, CH2-ciklopentil, CH2-tBu (neopentil), ciklopropil, ciklopentil, cikloheksil, 4-metoksicikloheksil, 4,4-dimetilcikloheksil, 3,3-dimetilcikloheksil, CH2-(pirid-3-il), 4-hidroksicikloheks-1-il, CH(CH3)CH(OH)fenil, CH(fenil)CH2OH, CH(tetrahidropiranil)CH2OH, CH2CH2CH2(imidazolil), CH2CH2 (morfolinil), CH2(tetrahidropiranil), CH2CH2(tetrahidropiranil), pirolidinil, piperidinil, tetrahidropiranil, tetrahidrofuranil, [image]
10. Spoj prema bilo kojem od zahtjeva 1 do 7, naznačen time, da R6 i R7 zajedno s dušikom na koji su priključeni tvore 4-7-člani heterociklički prsten, gdje je spomenuti heterociklički prsten opcijski supstituiran s jednom ili više skupina neovisno odabranih od sljedećih OH, halogen, okso, CF3, CH2CF3, CH2CH2OH, OCH3, C(=O)CH3, NH2, NHMe, N(Me)2, S(O)2CH3 i (C1-C3)alkil.
11. Spoj prema bilo kojem od zahtjeva 1 do 7 i 10, naznačen time, da NR6R7 je odabrana od sljedećih struktura: [image] [image]
12. Spoj prema bilo kojem zahtjevu 1 do 9, naznačen time, da NR6R7je NH2, NHMe, NHEt, NHPr, NHiPr, NHtBu, NH(CH2-tBu), NH(CH2-ciklopropil), NH(CH2-ciklobutil), NH(ciklopentil), NH(CH2-piridil), NH(cikloheksil), NH(3-pentil), NH-CH(izopropil)2, NH(CH2CH2OH), NH(CH2CH2CH2OH), NH(CH2CH2OMe), NH(CH2CH2CH2OMe), NH(CH2CN), NMe2, NMeEt, NMePr, NMe(iPr), NMe(CH2-ciklopropil), NMe(CH2-ciklobutil), NMe(CH2CH2OH), NMe(CH2CH2CH2OH), NMe(CH2CH2OMe), NMe(CH2CH2CH2OMe), NEt2, NEtPr, NEt(iPr), NEt(CH2-ciklopropil), NEt(CH2-ciklobutil), NEt(CH2CH2OH), NEt(CH2CH2CH2OH), [image]
13. Spoj formule IB, prema zahtjevu 2, naznačen time, da je odabran od sljedećih: (S)-3-amino-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropilamino)propan-1-on; (S)-3-amino-2-(3,4-diklorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin4-il)piperazin-1-il)propan-1-on; (S)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(metil(tetrahidro-2H-piran-4-il)amino)propan-1-on; (S)-2-(5-klorotiofen-2-il)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropilamino)propan-1-on; (S)-2-(4-klorofenil)3-(ciklopropilmetilamino)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropilamino)-2-(4-(trifluorometoksi)fenil)propan-1-on; (S)-2-(4-klorofenil)-3-(ciklopropilamino)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(3-hidroksiazetidin-1-il)propan-1-on; (S)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-((R)-pirolidin-3-ilamino)propan-1-on; (S)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-((S)-pirolidin-3-ilamino)propan-1-on; (S)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-tiomorfolinopropan-1-on; (S)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(piperazin-1-il)propan-1-on; (S)-2-(4-klorofenil)-3-(4-fluoropiperidin-1-il)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(3-metoksiazetidin-1-il)propan-1-on; (S)-2-(3,4-diklorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropilamino)propan-1-on; (S)-2-(4-klorofenil)-3-(dimetilamino)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-4-il)propan-1-on; (S)-2-(4-fluoro-3-(trifluorometil)fenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropilamino)propan-1-on; (S)-2-(3-fluoro-4-(trifluorometil)fenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropilamino)propan-1-on; (S)-2-(4-klorofenil)-1-(4((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(metoksiamino)propan-1-on; (S)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(4-metoksipiperidin-1-il)propan-1-on; (S)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(4-hidroksipiperidin-1-il)propan-1-on; (S)-3-(4-aminopiperidin-1-il)-2-(4-klorofenil)-1-((4-5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-2-(4-klorofenil)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(tetrahidro-2H-piran-4-ilamino)propan-1-on; (S)-2-(4-klorofenil)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(metil(tetrahidro-2H-piran-4-il)amino)propan-1-on; (S)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropil(metil)amino)propan-1-on; (S)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(4-(metilamino)piperidin-1-il)propan-1-on; (S)-2-(4-kloro-3-(trifluorometoksi)fenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropilamino)propan-1-on; (S)-2-(3-fluoro-4-(trifluorometoksi)fenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropilamino)propan-1-on; (5)-2-(4-kloro-3-(trifluorometil)fenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6-7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropilamino)propan-1-on; (S)-2-(4-klorofenil)-3-(4-etilpiperazin-1-il)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(4-izopropilpiperazin-1-il)propan-1-on; (S)-2-(4-klorofenil)-3-((S)-3-(dimetilamino)pirolidin-1-il)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-((R)-tetrahidrofuran-3-ilamino)propan-1-on; (S)-2-(4-klorofenil)-3-(2-fluoroetilamino)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-2-(4-fluoro-3-(trifluorometoksi)fenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropilamino)propan-1-on; (S)-2-(3-fluoro-4-metoksifenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropilamino)propan-1-on; (S)-2-(4-klorofenil)-3-(4-(dimetilamino)piperidin-1-il)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-2-(3-kloro-5-fluorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropilamino)propan-1-on; (S)-2-(3-bromo-4-metoksifenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropilamino)propan-1-on; (S)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(1,4-oksazepan-4-il)propan-1-on; (S)-2-(4-kloro-2-fluorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropilamino)propan-1-on; (S)-2-(2-fluoro-4-(trifluorometil)fenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropilamino)propan-1-on; (S)-2-(4-klorofenil)-3-(cikloheksilamino)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-2-(4-bromofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(4-izopropilpiperazin-1-il)propan-1-on; (S)-2-(4-bromofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(4-hidroksipiperidin-1-il)propan-1-on; (S)-3-(ciklopropilmetilamino)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-2-(4-(trifluorometil)fenil)propan-1-on; (S)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(tetrahidro-2H-piran-4-ilamino)-2-(4-(trifluorometil)fenil)propan-1-on; (S)-3-(ciklopropilmetilamino)-2-(2-fluoro-4-(trifluorometil)fenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-3-amino-2-(4-bromo-2-fluorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-2-(4-bromofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6-7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropil(metil)amino)propan-1-on; (S)-2-(4-bromo-2-fluorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropilamino)propan-1-on; (S)-3-amino-2-(4-kloro-2-fluorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-3-(tert-butilamino)-1-(4-((5R,7R)-7-hidroksi-5-metil-1-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-2-(4-(trifluorometil)fenil)propan-1-on; (S)-2-(4-kloro-2-fluorofenil)-3-(ciklopropilmetilamino)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-2-(4-bromo-2-fluorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(tetrahidro-2H-piran-4-ilamino)propan-1-on; (S)-2-(4-kloro-2-fluorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(tetrahidro-2H-piran-4-ilamino)propan-1-on; (S)-2-(4-bromofenil)-3-(tert-butilamino)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-2-(4-kloro-3-fluorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izobutilamino)propan-1-on; (S)-2-(4-kloro-3-fluorofenil)-3-(ciklopentilmetilamino)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-2-(4-kloro-3-fluorofenil)-3-(ciklopentilamino)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-2-(2-fluoro-4-(trifluorometil)fenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropil(metil)amino)propan-1-on; (S)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-((2-hidroksietil)(izopropil)amino)propan-1-on; (S)-3-amino-2-(2-fluoro-4-(trifluorometil)fenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-2-(4-bromofenil)-3-(4,4-dimetilcikloheksilamino)-1-(4-((SR,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-2-(4-bromofenil)-3-(3,3-dimetilcikloheksilamino)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-2-(4-klorofenil)-3-(4,4-dimetilcikloheksilamino)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-2-(4-klorofenil)-3-(3,3-dimetilcikloheksilamino)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropilamino)-2-(tiofen-2-il)propan-1-on; (S)-2-(5-bromotiofen-2-il)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropilamino)propan-1-on; (S)-2-(5-bromotiofen-2-il)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(tetrahidro-2H-piran-4-ilamino)propan-1-on; (R)-2-(5-bromopiridin-2-il)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropilamino)propan-1-on; (S)-2-(5-bromotiofen-2-il)-3-(ciklopropilmetilamino)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-2-(5-klorotiofen-2-il)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(tetrahidro-2H-piran-4-ilamino)propan-1-on; i (S)-2-(5-klorotiofen-2-il)-3-(ciklopropilmetilamino)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on.
14. Spoj prema zahtjevu 1, naznačen time, da je odabran od sljedećih: (S)-2-(4-klorofenil)-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropilamino)propan-1-on; (S)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(metil(tetrahidro-2H-piran-4-il)amino)propan-1-on; (S)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(3-hidroksiazetidin-1-il)propan-1-on; (S)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(R)-pirolidin-3-ilamino)propan-1-on; (S)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-((S)-pirolidin-3-ilamino)propan-1-on; (S)-3-(1-acetilpiperidin-4-ilamino)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(tetrahidro-2H-piran-4-ilamino)propan-1-on; (S)-2-(3,4-diklorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropilamino)propan-1-on; (S)-2-(4-klorofenil)-3-(dimetilamino)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropil(metil)amino)propan-1-on; (S)-2-(4-kloro-3-(trifluorometil)fenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropilamino)propan-1-on; (S)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(4-metoksicikloheksilamino)propan-1-on; (S)-2-(4-bromofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(tetrahidro-2H-piran-4-ilamino)propan-1-on; (R)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropilamino)propan-1-on; (S)-2-(4-klorofenil)-3-(ciklopropilmetilamino)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-2-(4-klorofenil)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropilamino)propan-1-on; (R)-2-(4-klorofenil)-3-(ciklopropilmetilamino)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (R)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(3-hidroksiazetidin-1-il)propan-1-on; (R)-3-(azetidin-1-il)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (R)-3-(4-acetilpiperazin-1-il)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (R)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(4-(2-hidroksietil)piperazin-1-il)propan-1-on; (R)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-morfolinopropan-1-on; (R)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(4-metilpiperazin-1-il)propan-1-on; (R)-3-(3-aminoazetidin-1-il)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (R)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(piperazin-1-il)propan-1-on; (R)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-tiomorfolinopropan-1-on; (R)-2-(4-klorofenil)-3-(4-fluoropiperidin-1-il)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (R)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(3-metoksiazetidin-1-il)propan-1-on; (R)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(4-metoksipiperidin-1-il)propan-1-on; (R)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(4-hidroksipiperidin-1-il)propan-1-on; (R)-3-(4-aminopiperidin-1-il)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-2-(4-klorofenil)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5Hciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(tetrahidro-2H-piran-4-ilamino)propan-1-on; (S)-2-(4-klorofenil)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(metil(tetrahidro-2H-piran-4-il)amino)propan-1-on; (R)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(4-(metilsulfonil)piperazin-1-il)propan-1-on; (R)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(4-(metilamino)piperidin-1-il)propan-1-on; (R)-2-(4-klorofenil)-3-(4-etilpiperazin-1-il)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (R)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(4-izopropilpiperazin-1-il)propan-1-on; (R)-2-(4-klorofenil)-3-((S)-3-(dimetilamino)pirolidin-1-il)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-2-(4-klorofenil)-1-(4-((5R,78)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-((R)-tetrahidrofuran-3-ilamino)propan-1-on; 4-((R)-2-(4-klorofenil)-3-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-oksopropil)piperazin-2-on; (R)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-((R)-3-hidroksipirolidin-1-il)propan-1-on; (R)-2-(4-klorofenil)-3-(4-(dimetilamino)piperidin-1-il)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (R)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(1,4-oksazepan-4-il)propan-1-on; (R)-2-(4-kloro-2-fluorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropilamino)propan-1-on; (S)-2-(4-klorofenil)-3-(cikloheksilamino)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (R)-3-(tert-butilamino)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (R)-2-(4-kloro-3-fluorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(4-metilpiperazin-1-il)propan-1-on; (R)-2-(4-kloro-3-fluorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-morfolinopropan-1-on; (R)-2-(3-fluoro-4-(trifluorometoksi)fenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(4-metilpiperazin-1-il)propan-1-on; (S)-3-amino-2-(4-bromofenil)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-3-amino-2-(4-kloro-3-fluorofenil)-1-(4-((5R,75)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; 3-((S)-2-(4-klorofenil)-3-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-oksopropilamino)propanamid; (S)-2-(4-bromofenil)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(tetrahidro-2H-piran-4-ilamino)propan-1-on; (S)-2-(4-kloro-3-fluorofenil)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(tetrahidro-2H-piran-4-ilamino)propan-1-on; (S)-3-amino-2-(3,4-diklorofenil)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (R)-2-(3,4-diklorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(4-hidroksipiperidin-1-il)propan-1-on; (R)-2-(3-fluoro-4-(trifluorometoksi)fenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(4-hidroksipiperidin-1-il)propan-1-on; (R)-3-(R)-3-aminopirolidin-1-il)-2-(4-klorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (R)-2-(3-fluoro-4-(trifluorometoksi)fenil)-1-(4-((SR,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-morfolinopropan-1-on; (R)-3-(4-etilpiperazin-1-il)-2-(3-fluoro-4-(trifluorometoksi)fenil)-1-(4-((SR,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (R)-3-(4-acetilpiperazin-1-il)-2-(3-fluoro-4-(trifluorometoksi)fenil)-1-(4-((SR,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-2-(3,4-diklorofenil)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(tetrahidro-2H-piran-4-ilamino)propan-1-on; (S)-2-(4-bromofenil)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropilamino)propan-1-on; (S)-2-(4-kloro-3-fluorofenil)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropilamino)propan-1-on; (S)-2-(4-kloro-3-fluorofenil)-3-(ciklopropilmetilamino)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-3-(bis(ciklopropilmetil)amino)-2-(4-kloro-3-fluorofenil)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-2-(4-bromofenil)-3-(ciklopropilmetilamino)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-2-(4-bromofenil)-3-((ciklopropilmetil)(metil)amino)-1-(4-((5R,75)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (R)-2-(4-klorofenil)-3-((3S,5R)-3,5-dimetilpiperazin-1-il)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (R)-2-(4-klorofenil)-3-((2S,6R)-2,6-dimetilmorfolino)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (R)-2-(3-fluoro-4-(trifluorometil)fenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(4-hidroksipiperidin-1-il)propan-1-on; (R)-2-(3-fluoro-4-(trifluorometil)fenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(4-metilpiperazin-1-il)propan-1-on; (R)-2-(3-fluoro-4-(trifluorometil)fenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(4-izopropilpiperazin-1-il)propan-1-on; (S)-3-amino-2-(4-bromo-3-fluorofenil)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-2-(3,4-diklorofenil)-1-(4((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3(izopropilamino)propan-1-on; (S)-2-(4-bromo-3-fluorofenil)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropilamino)propan-1-on; (S)-2-(4-bromo-3-fluorofenil)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(tetrahidro-2H-piran-4-ilamino)propan-1-on; (S)-2-(4-bromo-3-fluorofenil)-3-(ciklopropilmetilamino)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-2-(3-fluoro-4-(trifluorometil)fenil)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropilamino)propan-1-on; (R)-2-(4-bromo-3-fluorofenil)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(4-hidroksipiperidin-1-il)propan-1-on; (S)-2-(4-bromofenil)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropil(metil)amino)propan-1-on; (S)-3-amino-2-(4-bromo-2-fluorofenil)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-2-(4-bromo-2-fluorofenil)-1-(4-((5R,78)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropilamino)propan-1-on; (S)-2-(4-bromo-2-fluorofenil)-3-(ciklopropilmetilamino)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-2-(3-fluoro-4-(trifluorometoksi)fenil)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(tetrahidro-2H-piran-4-ilamino)propan-1-on; (S)-2-(3-fluoro-4-(trifluorometil)fenil)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(tetrahidro-2H-piran-4-ilamino)propan-1-on; (S)-2-(4-kloro-2-fluorofenil)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(tetrahidro-2H-piran-4-ilamino)propan-1-on; (S)-1-(4-((5R,75)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(tetrahidro-2H-piran-4-ilamino)-2-(4-(trifluorometil)fenil)propan-1-on; 5(S)-3-(ciklopropilmetilamino)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-2-(4-(trifluorometil)fenil)propan-1-on; (S)-2-(2-fluoro-4-(trifluorometil)fenil)-1-(4-((5R,75)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropilamino)propan-1-on; (S)-2-(2-fluoro-4-(trifluorometil)fenil)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(tetrahidro-2H-piran-4-ilamino)propan-1-on; (S)-3-(ciklopropilmetilamino)-2-(3-fluoro-4-(trifluorometil)fenil)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-3-(ciklopropilmetilamino)-2-(3-fluoro-4-(trifluorometoksi)fenil)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; (S)-2-(5-bromotiofen-2-il)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropilamino)propan-1-on; (S)-2-(5-bromopiridin-2-il)-1-(4-((5R,7R)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropilamino)propan-1-on; (S)-2-(5-bromotiofen-2-il)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(tetrahidro-2H-piran-4-ilamino)propan-1-on; (S)-2-(5-klorotiofen-2-il)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(tetrahidro-2H-piran-4-ilamino)propan-1-on; (S)-2-(5-klorotiofen-2-il)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)-3-(izopropilamino)propan-1-on; (S)-2-(5-klorotiofen-2-il)-3-(ciklopropilmetilamino)-1-(4-((5R,7S)-7-hidroksi-5-metil-6,7-dihidro-5H-ciklopenta[d]pirimidin-4-il)piperazin-1-il)propan-1-on; i njegove soli.
15. Farmaceutski sastav, naznačen time, da sadrži spoj prema bilo kojem od zahtjeva 1 do 14.
16. Spoj prema bilo kojem od zahtjeva 1 do 14, naznačen time, da se koristi u medicinskoj terapiji.
17. Spoj prema bilo kojem od zahtjeva 1 do 14, naznačen time, da se koristi za profilaktičko ili terapeutsko liječenje hiperproliferativnog poremećaja.
HR20110908T 2006-07-06 2011-12-02 Hidroksilirani i metoksilirani ciklopenta [d] pirimidini kao inhibitori kinaze akt proteina HRP20110908T1 (hr)

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