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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    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4245—Oxadiazoles
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    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
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    • C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
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    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
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    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

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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