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HRP20230201T1 - Oksadiazol aminski spojevi derivati kao inhibitor histonske deacetilaze 6 i farmaceutska kompozicija koja sadrži iste - Google Patents

Oksadiazol aminski spojevi derivati kao inhibitor histonske deacetilaze 6 i farmaceutska kompozicija koja sadrži iste Download PDF

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HRP20230201T1
HRP20230201T1 HRP20230201TT HRP20230201T HRP20230201T1 HR P20230201 T1 HRP20230201 T1 HR P20230201T1 HR P20230201T T HRP20230201T T HR P20230201TT HR P20230201 T HRP20230201 T HR P20230201T HR P20230201 T1 HRP20230201 T1 HR P20230201T1
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amine
oxadiazol
pyrimidin
difluoromethyl
cyclobutyl
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HRP20230201TT
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Yuntae Kim
Chang Sik Lee
Jung Taek Oh
Hyeseung SONG
Jin Choi
Jaeyoung Lee
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Chong Kun Dang Pharmaceutical Corp.
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Claims (10)

1. Oksadiazol aminski spoj derivat predstavljen sljedećom formulom I, stereoizomer istog ili farmaceutski prihvatljiva sol istog: [image] pri čemu R1 je -CF2H ili -CF3; L1 i L2 su svaki nezavisno -(C1-C2 alkilen)- ili veza; Z1 do Z4 su svaki nezavisno N ili CRZ {pri čemu tri ili više od Z1 do Z4 ne može biti N u isto vreme}, pri čemu RZ je -H, -F, -Cl, -Br, -I ili -O(C1-C4 alkil); R2 je -H ili -(C1-C4 alkil); Y1 je -CH2-, -NRc-, -O-, -C(=O)- ili -S(=O)2-, pri čemu Rc je -H, -(C1-C6 alkil), -(C1-C4 alkil)-OH, -(C1-C4 alkil)-O-(C1-C4 alkil), -C(=O)-(C1-C4 alkil), -C(=O)-O(C1-C4 alkil), -C(=O)-O(C1-C4 alkil)-aril, -(C1-C4 alkil)-C(=O)-O(C1-C4 alkil), -S(=O)2-(C1-C4 alkil), aril, -(C1-C4 alkil)-aril, -(C2-C4 alkenil)-aril, heteroaril, -(C1-C4 alkil)-heteroaril, -C(=O)-(C3-C7 cikloalkil), -(C2-C6 heterocikloalkil) ili -(C1-C4 alkil)-C(=O)-(C2-C6 heterocikloalkil), {pri čemu najmanje jedan H od -(C1-C6 alkil), -(C1-C4 alkil)-OH, -(C1-C4 alkil)-O-(C1-C4 alkil), -C(=O)-(C1-C4 alkil), -C(=O)-O(C1-C4 alkil), -C(=O)-O(C1-C4 alkil)-aril, -(C1-C4 alkil)-C(=O)-O(C1-C4 alkil), -S(=O)2-(C1-C4 alkil), aril, -(C1-C4 alkil)-aril, (C2-C4 alkenil)-aril, heteroaril, -(C1-C4 alkil)-heteroaril, -C(=O)-(C3-C7 cikloalkil), -C2-C6 heterocikloalkil ili -(C1-C4 alkil)-C(=O)-(C2-C6 heterocikloalkil) može biti supstituiran sa -X }; a i b su svaki nezavisno cijeli broj 0, 1, 2, 3 ili 4 {pri čemu a i b ne mogu svi biti 0}; L3 je -(C1-C2 alkilen)-, -SO2-, -(C1-C2 alkilen)-SO2-, ili veza; [image] je -aril, -heteroaril, [image] ili heterocikloalkil, pri čemu Z5 i Z6 su svaki nezavisno -CH2- ili -O-; i R4 do R6 su svaki nezavisno -H, -F, -Cl, -Br, -I, -OH, -O(C1-C4 alkil), -(C1-C4 alkil), -CF3, -OCF3, heterocikloalkil {pri čemu heterocikloalkil može biti nesupstituiran ili supstituiran sa C1-C4 alkilom ili heterocikloalkilom}, [image] -O-aril, -CF2H, -C(=O)-(C1-C4 alkil), -C(=O)-O(C1-C4 alkil), -NRARB, -C(=O)-NRARB ili -S(=O)2-(C1-C4 alkil), pri čemu Y2 je -CH2-, -O-, -C(=O)- ili -S(=O)2-, Y3 do Y5 su svaki nezavisno -CH- ili -N-, i c do f su svaki nezavisno cijeli broj 0, 1, 2, 3 ili 4{pri čemu c i e ne mogu svi biti 0, i d i f ne mogu svi biti 0}, pri čemu RA i RB su svaki nezavisno -H ili -(C1-C4 alkil) {pri čemu najmanje jedan H od -(C1-C4 alkil) može biti supstituiran sa -X ili -OH}, pri čemu X je F, Cl, Br ili I.
2. Oksadiazol aminski spoj derivat predstavljen formulom I, stereoizomer istog ili farmaceutski prihvatljiva sol istog prema patentnom zahtjevu 1, pri čemu R1 je -CF2H ili -CF3; L1 i L2 su veza; Z1 i Z3 su N; Z2 i Z4 su CRZ, pri čemu RZ je -H, -F, -Cl, -Br, -I ili -O(C1-C4 alkil); R2 je -H ili -(C1-C4 alkil); Y1 je -CH2- ili -NRc-, pri čemu Rc je -H, ili -C(=O)-O(C1-C4 alkil)-aril {pri čemu najmanje jedan H od -C(=O)-O(C1-C4 alkil)-aril može biti supstituiran sa -X, pri čemu X je F, Cl, Br ili I}; a i b su svaki nezavisno cijeli broj 0, 1, 2 ili 3 {pri čemu a i b ne mogu svi biti 0}; L3 je -(C1-C2 alkilen)-, (C1-C2 alkilen)-SO2-, ili veza; [image] je fenil, piridin, benzo[d][1,3]dioksol, tiofen, pirimidin, pirazin ili piridazin; i R4 do R6 su svaki nezavisno -H, -F, -Cl, -Br, -I, -OH, -O(C1-C4 alkil), -(C1-C4 alkil), -CF3, -OCF3, piperidin, morfolino, piperazin ili pirolidin {pri čemu piperidin, morfolino, piperazin ili pirolidin mogu biti nesupstituirani ili supstituirani sa C1-C4 alkilom}, ili [image] pri čemu Y2 je -O-. Y3 i Y5 su -CH-. Y4 je -N-. c i e su svaki nezavisno cijeli broj 0, 1 ili 2 {pri čemu c i e ne mogu svi biti 0}, i d i f su svaki nezavisno cijeli broj 0, 1, 2 ili 3 {pri čemu d i f ne mogu svi biti 0}.
3. Oksadiazol aminski spoj derivat predstavljen formulom I, stereoizomer istog ili farmaceutski prihvatljiva sol istog prema patentnom zahtjevu 1, pri čemu spoj predstavljen gore spomenutom formulom I je spoj predstavljen sljedećom formulom II : [image] pri čemu R1 je -CF2H ili -CF3; R2 je -H; Y1 je -CH2- ili -NRc-, pri čemu Rc je -H, ili -C(=O)-O(C1-C4 alkil)-aril; a i b su svaki nezavisno cijeli broj 0, 1, 2 ili 3 {pri čemu a i b ne mogu svi biti 0}, L3 je -(C1-C2 alkilen)-, (C1-C2 alkilen)-SO2-, ili veza; [image] je fenil, piridin, benzo[d][1,3]dioksol ili tiofen; i R4 do R6 su svaki nezavisno -H, -F, -Cl, -Br, -I, -OH, -O(C1-C4 alkil), -(C1-C4 alkil), -CF3, -OCF3, piperidin, morfolino {pri čemu piperidin može biti nesupstituiran ili supstituiran sa C1-C4 alkilom}, ili [image]
4. Oksadiazol aminski spoj derivat predstavljen formulom II, stereoizomer istog ili farmaceutski prihvatljiva sol istog prema patentnom zahtjevu 3, pri čemu R1 je -CF2H ili -CF3; R2 je -H; Y1 je -CH2- ili -NRc-, pri čemu Rc je -H, ili [image] a i b su svaki nezavisno cijeli broj 0, 1, 2 ili 3 {pri čemu a i b ne mogu svi biti 0, prsten formiran sa Y1, a i b je 3- do 7-člani zasićeni cikloalkil kada Y1 je-CH2- ili prsten formiran sa Y1, a i b je 3- do 7-člani zasićeni heterocikloalkil koji sadrži jedan N kada Y1 je -NRc-}; L3 je -CH2-, - CH2-SO2-, ili veza; [image] je fenil, piridin, benzo[d][1,3]dioksol ili tiofen; i R4 do R6 su svaki nezavisno -H, -F, -Cl, -Br, -I, -OH, -O(C1-C4 alkil), -(C1-C4 alkil), -CF3, -OCF3, morfolino, [image] ili [image] pri čemu R7 je -H ili -(C1-C4 alkil).
5. Oksadiazol aminski spoj derivat predstavljen formulom I, stereoizomer istog ili farmaceutski prihvatljiva sol istog prema patentnom zahtjevu 1, pri čemu spoj sa formulom I je odabran iz grupe koja se sastoji od sljedećih spojeva : 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-fenilciklopropil)pirimidin-2-amina; N-(1-fenilciklopropil)-5-(5-(trifluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-fenilciklobutil)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-fenilciklopentil)pirimidin-2-amina; N-(1-fenilciklopentil)-5-(5-(trifluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-fenilcikloheksil)pirimidin-2-amina; N-(1-fenilcikloheksil)-5-(5-(trifluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(4-metoksifenil)ciklobutil)pirimidin-2-amina; N-(1-(4-metoksifenil)ciklobutil)-5-(5-(trifluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(3-metoksifenil)ciklobutil)pirimidin-2-amina; N-(1-(3-metoksifenil)ciklobutil)-5-(5-(trifluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(3-fluorofenil)ciklobutil)pirimidin-2-amina; N-(1-(3-fluorofenil)ciklobutil)-5-(5-(trifluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(2-fluorofenil)ciklobutil)pirimidin-2-amina; N-(1-(2-fluorofenil)ciklobutil)-5-(5-(trifluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(4-fluorofenil)ciklobutil)pirimidin-2-amina; N-(1-(4-fluorofenil)ciklobutil)-5-(5-(trifluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; N-(1-(2-klorofenil)ciklobutil)-5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; N-(1-(3-klorofenil)ciklobutil)-5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; N-(1-(4-klorofenil)ciklobutil)-5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; N-(1-(2-klorofenil)ciklobutil)-5-(5-(trifluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina ; N-(1-(4-klorofenil)ciklobutil)-5-(5-(trifluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(piridin-2-il)ciklobutil)pirimidin-2-amina; N-(1-(piridin-2-il)ciklobutil)-5-(5-(trifluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(3-(trifluorometil)fenil)ciklobutil)pirimidin-2-amin; 5-(5-(trifluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(3-(trifluorometil)fenil)ciklobutil)pirimidin-2-amina; 5-(S-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(o-tolil)ciklobutil)pirimidin-2-amina; N-(1-(o-tolil)ciklobutil)-5-(5-(trifluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(m-tolil)ciklobutil)pirimidin-2-amina; N-(1-(m-tolil)ciklobutil)-5-(5-(trifluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(p-tolil)ciklobutil)pirimidin-2-amina; N-(1-(p-tolil)ciklobutil)-5-(5-(trifluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; Benzil 4-((5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-il)amino)-4-fenilpiperidin-1 -karboksilata; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(4-fenilpiperidin-4-il)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(2-fluorofenil)ciklopropil)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(4-fluorofenil)ciklopropil)pirimidin-2-amina; N-(1-(4-fluorofenil)ciklopropil)-5-(5-(trifluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(3-fluorofenil)ciklopropil)pirimidin-2-amina; N-(1-(3-fluorofenil)ciklopropil)-5-(5-(trifluorometil)-1, 3,4-oksadiazol-2-il)pirimidin-2-amina; N-(1-(3-kloro-4-fluorofenil)ciklopropil)-5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; N-(1-(3-kloro-4-fluorofenil)ciklopropil)-5-(5-(trifluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(4-(trifluorometil)fenil)ciklopropil)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(3-(trifluorometil)fenil)ciklopropil)pirimidin-2-amina; 5-(5-(trifluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(3-(trifluorometil)fenil)ciklopropil)pirimidin-2-amina; 5-(5-(trifluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(4-(trifluorometil)fenil)ciklopropil)pirimidin-2-amina; 3-(1-((5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-il)amino)ciklobutil)fenola; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(3,4-difluorofenil)ciklopropil)pirimidin-2-amina; N-(1-(3,4-difluorofenil)ciklopropil)-5-(5-(trifluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; N-(1-(3-kloro-4-fluorofenil)ciklobutil)-5-(5-(difluorometil)-1, 3,4-oksadiazol-2-il)pirimidin-2-amina; N-(1-(3-kloro-4-fluorofenil)ciklobutil)-5-(5-(trifluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(3,5-difluorofenil)ciklobutil)pirimidin-2-amina; N-(1-(benzo[d][1,3]dioksol-5-il)ciklobutil)-5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(2,5-difluorofenil)ciklobutil)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(4-(trifluorometoksi)fenil)ciklobutil)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(2,4,5-trifluorofenil)ciklobutil)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(2,3-difluorofenil)ciklobutil)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(2,6-difluorofenil)ciklobutil)pirimidin-2-amina N-(1-(2,3-diklorofenil)ciklobutil)-5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; N-(1-(2,3-diklorofenil)ciklobutil)-5-(5-(trifluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; N-(1-(3,4-diklorofenil)ciklobutil)-5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; N-(1-(3,4-diklorofenil)ciklobutil)-5-(5-(trifluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; N-(1-(2,4-diklorofenil)ciklobutil)-5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; N-(1-(2,4-diklorofenil)ciklobutil)-5-(5-(trifluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; N-(1-(2,6-diklorofenil)ciklobutil)-5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(piridin-3-il)ciklobutil)pirimidin-2-amina; N-(1-(2-kloro-4-fluorofenil}ciklobutil)-5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; N-(1-(2-kloro-4-fluorofenil)ciklobutil)-5-(5-(trifluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; N-(1-(2-kloro-5-fluorofenil)ciklobutil)-5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; N-(1-(2-kloro-5-fluorofenil)ciklobutil)-5-(5-(trifluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; N-(1-(5-kloro-2-fluorofenil)ciklobutil)-5-(5-(difluorometil)-1, 3,4-oksadiazol-2-il)pirimidin-2-amina; N-(1-(5-kloro-2-fluorofenil)ciklobutil)-5-(5-(trifluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; N-(1-(3-kloro-2-fluorofenil)ciklobutil)-5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; N-(1-(3-kloro-2-fluorofenil)ciklobutil)-5-(5-(trifluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(4-(1-(oksetan-3-il)piperidin-4-il)fenil)ciklobutil)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(tosilmetil)ciklobutil)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(2,4-difluorofenil)ciklobutil)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(2-(trifluorometoksi)fenil)ciklobutil)pirimidin-2-amina; N-(1-benzilciklobutil)-5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; N-(1-(2-(trifluorometoksi)fenil)ciklobutil)-5-(5-(trifluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; N-(1-(2,4-difluorofenil)ciklobutil)-5-(5-(trifluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oaadiazol-2-il)-N-(1-(4-(1-metilpiperidin-4-il)fenil)ciklobutil)pirimidin-2-amina; 5-(5-(difluorometil)-1, 3,4-oksadiazol-2-il)-N-(1-(4-{ 1-etilpiperidin-4-il)fenil)ciklobutil)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(4-(1-izopropilpiperidin-4-il)fenil)ciklobutil)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(tiofen-3-il)ciklobutil)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(tiofen-2-il)ciklopropil)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(4-(piperidin-1-il)fenil)ciklobutil)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(2-(trifluorometil)fenil)ciklobutil)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(4-(trifluorometil)fenil)ciklobutil)pirimidin-2-amina; 5-(5-(trifluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(4-(trifluorometil)fenil)ciklobutil)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(3,4-difluorofenil)ciklobutil)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(4-fluoro-3-morfolinofenil)ciklobutil)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(2-metoksifenil)ciklopropil)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(3-metoksifenil)ciklopropil)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(4-metoksifenil)ciklopropil)pirimidin-2-amina; N-(1-(3-klorofenil)ciklopropil)-5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; N-(1-(3-klorofenil)ciklopropil)-5-(5-(trifluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; N-(1-(4-klorofenil)ciklopropil)-5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; N-(1-(4-klorofenil)ciklopropil)-5-(5-(trifluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; N-(1-(4-kloro-3-fluorofenil)ciklopropil)-5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(o-tolil)ciklopropil)pirimidin-2-amina; N-(1-(4-kloro-2-fluorofenil)ciklopropil)-5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(3,5-difluorofenil)ciklopropil)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(3,4-difluorofenil)ciklopropil)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(3-(1-(oksetan-3-il)piperidin-4-il)fenil)ciklobutil)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(2,4-difluorofenil)ciklopropil)pirimidin-2-amina; i 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(4-morfolinofenil)ciklobutil)pirimidin-2-amina.
6. Oksadiazol aminski spoj derivat predstavljen formulom I, stereoizomer istog ili farmaceutski prihvatljiva sol istog prema patentnom zahtjevu 5, pri čemu spoj formule I je odabran iz grupe koja se sastoji od sljedećih spojeva : 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-fenilciklopropil)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-fenilciklobutil)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-fenilciklopentil)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(4-metoksifenil)ciklobutil)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(3-metoksifenil)ciklobutil)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiaaol-2-il)-N-(1-(3-fluorofenil)ciklobutil)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(2-fluorofenil)ciklobutil)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(4-fluorofenil)ciklobutil)pirimidin-2-amina; N-(1-(2-klorofenil)ciklobutil)-5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; N-(1-(3-klorofenil)ciklobutil)-5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; N-(1-(4-klorofenil)ciklobutil)-5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; i 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(piridin-2-il)ciklobutil)pirimidin-2-amina.
7. Oksadiazol aminski spoj derivat predstavljen formulom I, stereoizomer istog ili farmaceutski prihvatljiva sol istog prema patentnom zahtjevu 6, pri čemu spoj formule I je odabran iz grupe koja se sastoji od sljedećih spojeva : 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-fenilciklobutil)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(3-fluorofenil)ciklobutil)pirimidin-2-amina; 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(2-fluorofenil)ciklobutil)pirimidin-2-amina; N-(1-(2-klorofenil)ciklobutil)-5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; N-(1-(3-klorofenil)ciklobutil)-5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)pirimidin-2-amina; i 5-(5-(difluorometil)-1,3,4-oksadiazol-2-il)-N-(1-(piridin-2-il)ciklobutil)pirimidin-2-amina.
8. Farmaceutska kompozicija koja sadrži spoj predstavljen formulom I, stereoizomer istog ili farmaceutski prihvatljiva sol istog prema bilo kojem od patentnih zahtjeva 1 do 7.
9. Farmaceutska kompozicija za primjenu u prevenciji ili liječenju bolesti posredovanih histonskom deacetilazom, koja sadrži spoj predstavljen formulom I, stereoizomer istog ili farmaceutski prihvatljivu sol istog prema bilo kojem od patentnih zahtjeva 1 do 7, pri čemu bolest posredovana histonskom deacetilazom je odabrana od infektivnih bolesti; neoplazmi; endokrinih, nutritivnih i metaboličkih bolesti; mentalnih i poremećaja ponašanja; neuroloških bolesti; bolesti oka i adneksa; kardiovaskularnih bolesti; respiratornih bolesti; digestivnih bolesti; bolesti kože i potkožnog tkiva; bolesti mišićnokoštanog sustava i vezivnog tkiva; ili kongenitalnih malformacija, deformacija i kromosomalnih abnormalnosti.
10. Spoj predstavljen formulom I. stereoizomer istog ili farmaceutski prihvatljiva sol istog prema bilo kojem od patentnih zahtjeva 1 do 7 za primjenu u liječenju bolesti posredovanih histonskom deacetilazom, pri čemu je bolest posredovana histonskom deacetilazom odabrana od infektivnih bolesti; neoplazmi; endokrinih, nutritivnih i metaboličkih bolesti; mentalnih i poremećaja ponašanja; neuroloških bolesti; bolesti oka i adneksa; kardiovaskularnih bolesti; respiratornih bolesti; digestivnih bolesti; bolesti kože i potkožnog tkiva; bolesti mišićnokoštanog sustava i vezivnog tkiva; ili kongenitalnih malformacija, deformacija i kromosomalnih abnormalnosti.
HRP20230201TT 2015-10-12 2016-10-11 Oksadiazol aminski spojevi derivati kao inhibitor histonske deacetilaze 6 i farmaceutska kompozicija koja sadrži iste HRP20230201T1 (hr)

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