HRP20230546T1 - Heteroaromatski spojevi i njihova upotreba kao dopaminskih d1 liganada - Google Patents

Heteroaromatski spojevi i njihova upotreba kao dopaminskih d1 liganada Download PDF

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HRP20230546T1
HRP20230546T1 HRP20230546TT HRP20230546T HRP20230546T1 HR P20230546 T1 HRP20230546 T1 HR P20230546T1 HR P20230546T T HRP20230546T T HR P20230546TT HR P20230546 T HRP20230546 T HR P20230546T HR P20230546 T1 HRP20230546 T1 HR P20230546T1
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alkyl
cycloalkyl
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alkoxy
halogen
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HRP20230546TT
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Michael Aaron Brodney
Jennifer Elizabeth Davoren
Amy Beth Dounay
Ivan Viktorovich Efremov
David Lawrence Firman Gray
Michael Eric GREEN
Jaclyn Louise HENDERSON
Chewah LEE
Scot Richard MENTE
Steven Victor O'neil
Bruce Nelsen Rogers
Lei Zhang
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Pfizer Inc.
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Claims (21)

1. Spoj Formule IB-8: [image] , ili njegova farmaceutski prihvatljiva sol, naznačen time što: svakog od T1, T2, T3, te T4 se neovisno bira iz skupine koju čine H, halogen, -CN, -SF5, -OH, -N(Ra)(Rb), -C(=O)-N(Ra)(Rb), -C(=O)-ORc, -C(=O)-Rd, C1-6 alkil, C1-6 halogenalkil, C2-6 alkenil, C2-6 alkinil, C1-6 alkoksi, C1-6 halogenalkoksi, -S-(C1-6 alkil), C3-7 cikloalkil, 4- do 7-eročlani heterocikloalkil, C3-7 cikloalkoksi, 5- ili 6-eročlani heteroaril, ciklopropilmetil, te ciklobutilmetil, gdje svaki od C1-6 alkila, C2-6 alkenil, C2-6 alkinil, -S-(C1-6 alkil), te C1-6 alkoksi može biti supstituiran s jednim ili više supstituenata, od kojih se svakog neovisno bira iz skupine koju čine halogen, -OH, -CN, -N(Ra)(Rb), C1-4 alkoksi, C1-4 halogenalkoksi, te -S-(C1-4 alkil); te gdje svaki od C3-7 cikloalkila, 4- do 7-eročlanog heterocikloalkila, C3-7 cikloalkoksi, 5- ili 6-eročlanog heteroarila, ciklopropilmetila, te ciklobutilmetila u T1, T2, te T3 može biti supstituiran s jednim ili više supstituenata, od kojih se svakog neovisno bira iz skupine koju čine halogen, -OH, -CN, okso, -N(Ra)(Rb), -C(=O)OH, -C(=O)-C1-4 alkil, -C(=O)-O-C1-4 alkil, -C(=O)-N(Ra)(Rb), C1-4 alkil, C1-4 halogenalkil, C1-4 hidroksilalkil, C1-4 cijanoalkil, C1-4 alkoksi, C1-4 halogenalkoksi, te -S-(C1-4 alkil); svakog od Ra i Rb se neovisno bira iz skupine koju čine H, C1-4 alkil, C3-7 cikloalkil, te ciklopropilmetil; ili Ra i Rb, zajedno s N atomom na kojeg su vezani, tvore 4- do 7-eročlani heterocikloalkil, koji može biti supstituiran s jednim ili više supstituenata, od kojih se svakog neovisno bira iz skupine koju čine halogen, -OH, -CN, okso, -NH2, -NH(C1-4 alkil), -N(C1-4 alkil)2, -C(=O)OH, -C(=O)-C1-4 alkil, -C(=O)-O-C1-4 alkil, -C(=O)-NH2, -C(=O)-NH(C1-4 alkil), - C(=O)-N(C1-4 alkil)2, C1-4 alkil, C1-4 halogenalkil, C1-4 hidroksilalkil, C1-4 cijanoalkil, C1-4 alkoksi, -S-(C1-4 alkil), te C1-4 halogenalkoksi; svaki od Rc i Rd je neovisno C1-4 alkil, C3-4 cikloalkil-C1-2 alkil- ili C3-4 cikloalkil; svakog od R1, R2, R3, te R4 se neovisno bira iz skupine koju čine H, halogen, -OH, -NO2, -CN, -SF5, C1-6 alkil, C1-6 halogenalkil, C1-6 halogenalkoksi, C2-6 alkenil, C2-6 alkinil, C3-7 cikloalkil, 4- do 10-eročlani heterocikloalkil, -N(R5)(R6), -N(R7)(C(=O)R8), -C(=O)-N(R5)(R6), -C(=O)-R8, -C(=O)-OR8, -N(R7)(S(=O)2R8), -S(=O)2-N(R5)(R6), -SR8, te -OR8, gdje svaki od C1-6 alkila, C3-7 cikloalkila, te heterocikloalkila može biti supstituiran s 1, 2 ili 3 supstituenta, od kojih se svakog neovisno bira iz skupine koju čine halogen, -CN, okso, -OH, C1-4 alkil, C1-4 alkoksi, C1-4 halogenalkil, C1-4 halogenalkoksi, C3-6 cikloalkil, -N(R5)(R6), -N(R7)(C(=O)R8), -C(=O)-OR8, -C(=O)H, -C(=O)R8, -C(=O)N(R5)(R6), -N(R7)(S(=O)2R8), -S(=O)2-N(R5)(R6), -SR8, te -OR8; ili R2 i R4, zajedno s dva atoma ugljika na koje su vezani, tvore kondenzirani 5- ili 6-eročlani heteroaril, kondenzirani 5- ili 6-eročlani heterocikloalkilni prsten, kondenzirani 5- ili 6-eročlani cikloalkilni prsten, ili kondenzirani benzenski prsten, gdje svaki od kondenziranih prstena može biti supstituiran s 1, 2 ili 3 supstituenta, od kojih se svakog neovisno bira iz skupine koju čine halogen, -CN, -OH, C1-4 alkil, C1-4 alkoksi, C1-4 halogenalkil, te C1-4 halogenalkoksi, te gdje je kondenzirani heterocikloalkilni prsten ili kondenzirani cikloalkilni prsten dalje izborno supstituiran s 1, 2 ili 3 okso; R5 je H, C1-4 alkil, C1-4 halogenalkil ili C3-7 cikloalkil; R6 je H ili se bira iz skupine koju čine C1-4 alkil, C1-4 halogenalkil, C3-7 cikloalkil, 4- do 10-eročlani heterocikloalkil, C6-10 aril, 5- do 10-eročlani heteroaril, (C3-7 cikloalkil)-C1-4 alkil-, (4- do 10-eročlani heterocikloalkil)-C1-4 alkil-, (C6-10 aril)-C1-4 alkil-, te (5- do 10-eročlani heteroaril)-C1-4 alkil-, gdje svaki od odabira iz skupine može biti supstituiran s 1, 2, 3 ili 4 supstituenta, od kojih se svakog neovisno bira iz skupine koju čine -OH, -CN, C1-4 alkil, C3-7 cikloalkil, C1-4 hidroksilalkil, -S-C1-4 alkil, -C(=O)H, -C(=O)-C1-4 alkil, -C(=O)-O-C1-4 alkil, -C(=O)-NH2, -C(=O)-N(C1-4 alkil)2, C1-4 halogenalkil, C1-4 alkoksi, te C1-4 halogenalkoksi; ili R5 i R6, zajedno s N atomom na kojeg su vezani, tvore 4- do 10-eročlani heterocikloalkil ili 5- do 10-eročlani heteroaril, od kojih svaki može biti supstituiran s 1, 2, 3, 4 ili 5 supstituenata, od kojih se svakog neovisno bira iz skupine koju čine halogen, -OH, okso, -C(=O)H, -C(=O)-C1-4 alkil, -C(=O)OH, -C(=O)-OC1-4 alkil, -C(=O)-NH2, -C(=O)-N(C1-4 alkil)2, -CN, C1-4 alkil, C1-4 alkoksi, C1-4 hidroksilalkil, C1-4 halogenalkil, te C1-4 halogenalkoksi; R7 se bira iz skupine koju čine H, C1-4 alkil, te C3-7 cikloalkil; R8 se bira iz skupine koju čine C1-6 alkil, C3-7 cikloalkil, 4- do 10-eročlani heterocikloalkil, C6-10 aril, 5- do 10-eročlani heteroaril, (C3-7 cikloalkil)-C1-4 alkil-, (4- do 10-eročlani heterocikloalkil)-C1-4 alkil-, (C6-10 aril)-C1-4 alkil-, te (5- do 10-eročlani heteroaril)-C1-4 alkil-, gdje svaki od odabira iz skupine može biti supstituiran s 1, 2 ili 3 supstituenta, od kojih se svakog neovisno bira iz skupine koju čine halogen, -CF3, -CN, -OH, okso, -S-C1-4 alkil, C1-4 alkil, C1-4 halogenalkil, C2-6 alkenil, C2-6 alkinil, C3-7 cikloalkil, C1-4 alkoksi, te C1-4 halogenalkoksi; R10 se bira iz skupine koju čine halogen, -OH, -CN, -SF5, -NO2, C1-6 alkil, C1-6 halogenalkil, C1-6 hidroksilalkil, C1-6 alkoksi, C1-6 halogenalkoksi, C3-7 cikloalkil, C2-6 alkenil, C2-6 alkinil, C6-10 aril, 4- do 10-eročlani heterocikloalkil, 5- do 10-eročlani heteroaril, (C3-7 cikloalkil)-C1-4 alkil-, (4- do 10-eročlani heterocikloalkil)-C1-4 alkil-, (C6-10 aril)-C1-4 alkil-, (5- do 10-eročlani heteroaril)-C1-4 alkil-, -N(R5)(R6), -N(R7)(C(=O)R8), -S(=O)2N(R5)(R6), -C(=O)-N(R5)(R6), -C(=O)-R8, -C(=O)-OR8, -SR8, te -OR8, gdje svaki od C1-6 alkila, C3-7 cikloalkila, C6-10 arila, 4- do 10-eročlanog heterocikloalkila, 5- do 10-eročlanog heteroarila, (C3-7 cikloalkil)-C1-4 alkila-, (4- do 10-eročlani heterocikloalkil)-C1-4 alkila-, (C6-10 aril)-C1-4 alkila-, te (5- do 10-eročlani heteroaril)-C1-4 alkila- može biti supstituiran s 1, 2, 3 ili 4 supstituenta, od kojih se svakog neovisno bira iz skupine koju čine halogen, -OH, -CN, -NO2, C1-4 alkil, C1-4 hidroksilalkil, C1-4 alkoksi, -N(R5)(R6), -S-(C1-4 alkil), -S(=O)2-(C1-4 alkil), C6-10 ariloksi, [(C6-10 aril)-C1-4 alkiloksi- izborno supstituiran s 1 ili 2 C1-4 alkila], okso, -C(=O)H, -C(=O)-C1-4 alkil, -C(=O)O-C1-4 alkil, -C(=O)NH2, -NHC(=O)H, -NHC(=O)-(C1-4 alkil), C3-7 cikloalkil, 5- ili 6-eročlani heteroaril, C1-4 halogenalkil, te C1-4 halogenalkoksi; R10B se bira iz skupine koju čine H, C1-6 alkil, C1-6 halogenalkil, C1-6 hidroksilalkil, C3-7 cikloalkil, C3-6 alkenil, C3-6 alkinil, C6-10 aril, 4- do 10-eročlani heterocikloalkil, 5- do 10-eročlani heteroaril, (C3-7 cikloalkil)-C1-4 alkil-, (4- do 10-eročlani heterocikloalkil)-C1-4 alkil-, (C6-10 aril)-C1-4 alkil-, (5- do 10-eročlani heteroaril)-C1-4 alkil-, -S(=O)2N(R5)(R6), -C(=O)-N(R5)(R6), -C(=O)-R8, te -C(=O)-OR8, gdje svaki od C1-6 alkila, C3-7 cikloalkila, C6-10 arila, 4- do 10-eročlanog heterocikloalkila, 5- do 10-eročlanog heteroarila, (C3-7 cikloalkil)-C1-4 alkila-, (4- do 10-eročlani heterocikloalkil)-C1-4 alkila-, (C6-10 aril)-C1-4 alkila-, te (5- do 10-eročlani heteroaril)-C1-4 alkila- može biti supstituiran s 1, 2, 3 ili 4 supstituenta, od kojih se svakog neovisno bira iz skupine koju čine halogen, -OH, -CN, -NO2, C1-4 alkil, C1-4 hidroksilalkil, C1-4 alkoksi, -N(R5)(R6), -S-(C1-4 alkil), -S(=O)2-(C1-4 alkil), C6-10 ariloksi, [(C6-10 aril)-C1-4 alkiloksi- izborno supstituiran s 1 ili 2 C1-4 alkila], okso, -C(=O)H, -C(=O)-C1-4 alkil, -C(=O)O-C1-4 alkil, -C(=O)NH2, -NHC(=O)H, -NHC(=O)-(C1-4 alkil), -OC(=O)-C1-4 alkil, C3-7 cikloalkil, 5- ili 6-eročlani heteroaril, C1-4 halogenalkil, te C1-4 halogenalkoksi.
2. Spoj u skladu s patentnim zahtjevom 1, ili njegova farmaceutski prihvatljiva sol, naznačen time što: R10 se bira iz skupine koju čine -CN, C1-4 alkil, C3-4 cikloalkil, ciklopropilmetil, te ciklobutilmetil, gdje C1-4 alkil u R10 može biti supstituiran s jednim ili više supstituenata, od kojih se svakog neovisno bira iz skupine koju čine halogen, -OH, -CN, C1-4 alkoksi, te C1-4 halogenalkoksi; te gdje svaki od C3-4 cikloalkila, ciklopropilmetila, te ciklobutilmetila u R10 može biti supstituiran s jednim ili više supstituenata, od kojih se svakog neovisno bira iz skupine koju čine halogen, -OH, -CN, C1-4 alkil, C1-4 halogenalkil, C1-4 hidroksilalkil, C1-4 cijanoalkil, C1-4 alkoksi, te C1-4 halogenalkoksi; i R10B se bira iz skupine koju čine C1-4 alkil, C3-4 cikloalkil, ciklopropilmetil, te ciklobutilmetil, gdje C1-4 alkil u R10B može biti supstituiran s jednim ili više supstituenata, od kojih se svakog neovisno bira iz skupine koju čine halogen, -OH, -CN, C1-4 alkoksi, te C1-4 halogenalkoksi; te gdje svaki od C3-4 cikloalkila, ciklopropilmetila, te ciklobutilmetila u R10B može biti supstituiran s jednim ili više supstituenata, od kojih se svakog neovisno bira iz skupine koju čine halogen, -OH, -CN, C1-4 alkil, C1-4 halogenalkil, C1-4 hidroksilalkil, C1-4 cijanoalkil, C1-4 alkoksi, te C1-4 halogenalkoksi.
3. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 ili 2, ili njegova farmaceutski prihvatljiva sol, naznačen time što: svakog od R10 i R10B se neovisno bira iz skupine koju čine C1-3 alkil, C1-3 halogenalkil, te ciklopropil.
4. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 3, ili njegova farmaceutski prihvatljiva sol, naznačen time što svaki od R10 i R10B je neovisno metil ili etil.
5. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 4, ili njegova farmaceutski prihvatljiva sol, naznačen time što se svakog od R1 i R2 neovisno bira iz skupine koju čine H, halogen, -CN, C1-6 alkil, C1-6 halogenalkil, C1-6 alkoksi, C1-6 halogenalkoksi, C3-6 cikloalkil, -C(=O)-(C1-4 alkil), -C(=O)OH, te C(=O)-O-(C1-4 alkil), gdje svaki od C1-6 alkila i C3-6 cikloalkila može biti supstituiran s 1, 2, 3, 4 ili 5 supstituenata, od kojih se svakog neovisno bira između halogena, -OH, -CN, C1-4 alkil, C1-4 halogenalkila, C1-4 alkoksi, te C1-4 halogenalkoksi.
6. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 5, ili njegova farmaceutski prihvatljiva sol, naznačen time što je svaki od R1 i R2 neovisno H, metil ili halogen.
7. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 6, ili njegova farmaceutski prihvatljiva sol, naznačen time što je svaki od R1 i R2 H.
8. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 7, ili njegova farmaceutski prihvatljiva sol, naznačen time što se svakog od R3 i R4 neovisno bira iz skupine koju čine H, halogen, -CN, - C1-4 alkil, C1-4 alkoksi, te C3-4 cikloalkil, gdje svaki od C1-4 alkila i C1-4 alkoksi u R3 i R4 može biti supstituiran s 1, 2, 3, 4 ili 5 supstituenata, od kojih se svakog neovisno bira između halogena, -OH, C1-4 alkoksi, te C1-4 halogenalkoksi; te gdje C3-4 cikloalkil u R3 i R4 može biti supstituiran s 1, 2, 3, 4 ili 5 supstituenata, od kojih se svakog neovisno bira između halogena, -OH, C1-4 alkila, C1-4 halogenalkila, C1-4 alkoksi, te C1-4 halogenalkoksi.
9. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 8, ili njegova farmaceutski prihvatljiva sol, naznačen time što je R3 H; a R4 je H, halogen ili metil, gdje metil može biti supstituiran s 1, 2 ili 3 supstituenta, od kojih se svakog neovisno bira iz skupine koju čine halogen, -OH, te C1-4 alkoksi.
10. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 9, ili njegova farmaceutski prihvatljiva sol, naznačen time što je R3 H, a R4 je metil.
11. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 10, ili njegova farmaceutski prihvatljiva sol, naznačen time što se svakog od T1, T2, T3, te T4 neovisno bira iz skupine koju čine H, halogen, -CN, C1-4 alkil, C1-4 halogenalkil, C2-4 alkenil, C1-4 alkoksi, C1-4 halogenalkoksi, te C3-4 cikloalkil, gdje svaki od C1-4 alkila, C2-4 alkenila, te C1-4 alkoksi u T1, T2, T3, te T4 može biti supstituiran s jednim ili više supstituenata, od kojih se svakog neovisno bira iz skupine koju čine halogen, -OH, -CN, C1-4 alkoksi, te C1-4 halogenalkoksi; te gdje C3-4 cikloalkil u T1, T2, T3, te T4 može biti supstituiran s jednim ili više supstituenata, od kojih se svakog neovisno bira iz skupine koju čine halogen, -OH, -CN, C1-4 alkil, C1-4 halogenalkil, C1-4 hidroksilalkil, C1-4 cijanoalkil, C1-4 alkoksi, te C1-4 halogenalkoksi.
12. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 11, ili njegova farmaceutski prihvatljiva sol, naznačen time što se svakog od T1, T2, T3, te T4 neovisno bira iz skupine koju čine H, halogen, C1-4 alkil, C1-4 hidroksilalkil, C1-4 halogenalkil, C1-4 alkoksi, C1-4 halogenalkoksi, C3-4 cikloalkil, te C3-4 halogencikloalkil.
13. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 12, ili njegova farmaceutski prihvatljiva sol, naznačen time što se T1 bira iz skupine koju čine halogen, ciklopropil, halogenciklopropil, metil, C1 halogenalkil, metoksi, te C1 halogenalkoksi; a T4 je H.
14. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je 6-{4-[(3-klor-4-metilpiridin-2-il)oksi]fenil}-1,5-dimetilpirimidin-2,4(1H,3H)-dion, ili njegova farmaceutski prihvatljiva sol.
15. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je (–)-6-(4-{[3-(difluormetoksi)piridin-2-il]oksi}-2-metilfenil)-1,5-dimetilpirimidin-2,4(1H,3H)-dion, ili njegova farmaceutski prihvatljiva sol.
16. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je 1,5-dimetil-6-(2-metil-4-{[3-(trifluormetoksi)piridin-2-il]oksi}fenil)pirimidin-2,4(1H,3H)-dion, ili njegova farmaceutski prihvatljiva sol.
17. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je (–)-6-{4-[(3-klorpiridin-2-il)oksi]-2-metilfenil}-1,5-dimetilpirimidin-2,4(1H,3H)-dion, ili njegova farmaceutski prihvatljiva sol.
18. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je 6-{4-[(3-ciklopropilpiridin-2-il)oksi]fenil}-1,5-dimetilpirimidin-2,4(1H,3H)-dion, ili njegova farmaceutski prihvatljiva sol.
19. Farmaceutski pripravak, naznačen time što sadrži spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 18, ili njegovu farmaceutski prihvatljivu sol, kao i farmaceutski prihvatljivi nosač.
20. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 18, ili njegova farmaceutski prihvatljiva sol, naznačen time što je namijenjen upotrebi u liječenju poremećaja kojeg se bira između shizofrenije, kognitivnog poremećaja, poremećaja nedostatka pažnje uz hiperaktivnost (ADHD), impulzivnosti, kompulzivnog kockanja, prejedanja, spektra autističnih poremećaja, blagog kognitivnog poremećaja (MCI), opadanja kognitivnih funkcija povezanog sa starenjem, demencije, sindroma nemirnih nogu (RLS), Parkinsonove bolesti, Huntingtonove koreje, anksioznosti, depresije, velikog depresivnog poremećaja (MDD), depresije koja ne reagira na liječenje (TRD), bipolarnog poremećaja, kronične apatije, anhedonija, kronične zamorenosti, posttraumatskog stresnog poremećaja, sezonskog afektivnog poremećaja, socijalnog anksioznog poremećaja, poslijeporođajne depresije, serotoninskog sindroma, zloupotrebe tvari i ovisnosti o narkoticima, recidiva zloupotrebe narkotika, Touretteovog sindroma, tardivne diskinezije, pospanosti, prekomjerne pospanosti po danu, kaheksije, nepažljivosti, spolne disfunkcije, migrene, sistemnog eritemskog lupusa (SLE), hiperglikemije, ateroskleroze, dislipidemija, pretilosti, dijabetesa, sepse, postishemične tubularne nekroze, zatajenja bubrega, hiponatrijemije, otpornog edema, narkolepsije, hipertenzije, kongestivnog zatajenja srca, poslijeoperativne očne hipotonije, poremećaja spavanja, te boli.
21. Spoj namijenjen upotrebi u skladu s patentnim zahtjevom 20, naznačen time što se poremećaj bira između shizofrenije, kognitivnog poremećaja, blagog kognitivnog poremećaja (MCI), opadanja kognitivnih funkcija povezanog sa starenjem, demencije, te Parkinsonove bolesti.
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