HRP20220598T1 - Derivati kinolina za liječenje upalnih bolesti - Google Patents

Derivati kinolina za liječenje upalnih bolesti Download PDF

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HRP20220598T1
HRP20220598T1 HRP20220598TT HRP20220598T HRP20220598T1 HR P20220598 T1 HRP20220598 T1 HR P20220598T1 HR P20220598T T HRP20220598T T HR P20220598TT HR P20220598 T HRP20220598 T HR P20220598T HR P20220598 T1 HRP20220598 T1 HR P20220598T1
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Croatia
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chloro
quinolin
trifluoromethoxy
amine
group
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HRP20220598TT
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Jamal Tazi
Romain Najman
Florence Mahuteau
Didier Scherrer
Michael Hahne
Karim Chebli
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Abivax
Cnrs Centre National De La Recherche Scientifique
Institut Curie
Université De Montpellier
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Publication of HRP20220598T1 publication Critical patent/HRP20220598T1/hr

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Claims (13)

1. Spoj s formulom (I) [image] naznačen time što: Z je C ili N, V je C ili N, [image] predstavlja aromatski prsten pri čemu V je C ili N i kada V je N, V je u orto, meta ili para od Z, tj. tvori piridinsku, piridazinsku, pirimidinsku ili pirazinsku skupinu, R neovisno predstavljaju vodikov atom, metilnu skupinu, metoksi skupinu, trifluormetilnu skupinu, trifluormetoksi skupinu, amino skupinu, halogeni atom i skupinu -O-P(=O)-(OR3)(OR4) i točnije atom fluora ili klora, trifluormetoksi skupinu i amino skupinu, Q je N ili O, pod uvjetom da R" ne postoji kada Q je O, R3 i R4 neovisno predstavljaju vodikov atom, Li+, Na+, K+, N+(Ra)4 ili benzilnu skupinu, Ra predstavlja vodikov atom, skupinu (C1-C5)alkil ili skupinu (C3-C6)cikloalkil, n je 1, 2 ili 3, n' je 1, 2 ili 3, R' neovisno predstavljaju vodikov atom, halogeni atom i točnije atom fluora ili klora, amino skupinu, metilnu skupinu, skupinu -O-P(=O)-(OR3)(OR4) ili skupinu [image] pri čemu A je O ili NH, m je 2 ili 3 i X1 je O, CH2 ili N-CH3, pod uvjetom da kada R' je takva skupina, n' je 1 ili 2, i kada n' je 2, druga R' skupina je različita od navedene skupine ili alternativno R' neovisno predstavlja vodikov atom, halogeni atom i točnije atom fluora ili klora, metilna skupina ili skupina [image] , pri čemu A je O ili NH, m je 2 i X1 je O, CH2 ili N-CH3, pod uvjetom da kada R' je takva skupina, n' je 1 ili 2, i kada n' je 2, druga R' skupina je različita od navedene skupine, R" je vodikov atom, skupina (C1-C4)alkil ili skupina [image] pri čemu m je 2 ili 3 i X1 je O, CH2 ili N-CH3, ili bilo koja njegova farmaceutski prihvatljiva sol, za uporabu u liječenju i/ili prevenciji upalnih bolesti, pri čemu je navedena upalna bolest odabrana s popisa koji se sastoji od: upalne bolesti crijeva, Crohnove bolesti, ulceroznog kolitisa, multiple skleroze, osteoartritisa, ankilozantnog spondilitisa, psorijaze, Sjogrenovog sindroma, bronhitisa, astme i upale povezane s karcinomom debelog crijeva.
2. Spoj za upotrebu prema patentnom zahtjevu 1, naznačen time što Q je N.
3. Spoj za upotrebu prema patentnom zahtjevu 1 ili 2, naznačen time što je odabran od [image] [image] i [image] pri čemu R, R', R", n i n' su kako je definirano u zahtjevu 1.
4. Spoj za upotrebu prema prethodnom zahtjevu, odabran od [image] naznačen time što su R, R', R", n i n' kako je definirano u zahtjevu 1.
5. Spoj za upotrebu prema bilo kojem od prethodnih zahtjeva, naznačen time što je spoj s formulom (I) spoj s formulom (24) [image] i upalna bolest je upalna bolest crijeva.
6. Spoj s formulom (24) [image] za uporabu u liječenju reumatoidnog artritisa.
7. Spoj s formulom (Id): [image] naznačen time što su R, R', n i n' kako je definirano u zahtjevu 1.
8. Spoj s formulom (Ie) [image] pri čemu su R, R', n i n' kako je definirano u zahtjevu 1, za upotrebu u liječenju i/ili prevenciji upalne bolesti, pri čemu je navedena upalna bolest odabrana s popisa koji se sastoji od: upalne bolesti crijeva, Crohnove bolesti, ulceroznog kolitisa , multiple skleroze, osteoartritisa, ankilozantnog spondilitisa, psorijaze, Sjogrenovog sindroma, bronhitisa, astme i upale povezane s karcinomom debelog crijeva.
9. Spoj odabran s popisa koji sadrži: - (8) 8-klor-5-(3-(piperidin-1-il)propoksi)-N-(4-(trifluormetil)piridin-2-il)kinolin-2-amin - (9) 8-klor-N4-(3-(piperidin-1-il)propil)-N2-(4-(trifluormetil)piridin-2-il)kinolin-2,4-diamin - (10) 8-klor-N-metil-N-(4-(trifluormetil)piridin-2-il)kinolin-2-amin - (11) 8-klor-N4-(2-morfolinoetil)-N2-(4-(trifluormetil)piridin-2-il)kinolin-2,4-diamin - (13) 4,8-diklor-N-(4-(trifluormetil)piridin-2-il)kinolin-2-amin - (14) 8-klor-N-(3-morfolinopropil)-N-(4-(trifluormetil)piridin-2-il)kinolin-2-amin - (15) 8-klor-6-(2-morfolinoetoksi)-N-(3-morfolinopropil)-N-(4-(trifluormetil)piridin-2-il)kinolin-2-amin - (16) 8-klor-5-(2-morfolinoetoksi)-N-(3-morfolinopropil)-N-(4-(trifluormetil)piridin-2-il)kinolin-2-amin - (17) 8-klor-6-(2-(4-metilpiperazin-1-il)etoksi)-N-(4-(trifluormetil)piridin-2-il)kinolin-2-amin - (18) 8-klor-6-(2-(piperidin-1-il)etoksi)-N-(4-(trifluormetil)piridin-2-il)kinolin-2-amin - (19) 8-klor-6-(3-(piperidin-1-il)propoksi)-N-(4-(trifluormetil)piridin-2-il)kinolin-2-amin - (20) 8-klor-N-(3-fluor-4-(trifluormetil)piridin-2-il)kinolin-2-amin - (21) N-(5-bromo-4-(trifluormetil)piridin-2-il)-8-klorkinolin-2-amin - (22) N2-(8-klorkinolin-2-il)-N5-(3-(4-metilpiperazin-1-il)propil)-4-(trifluormetil)piridine-2,5-diamin - (28) 8-klor-N-metil-N-(4-(trifluormetoksi)fenil)kinolin-2-amin - (29) 8-klor-5-(3-(piperidin-1-il)propoksi)-N-(4-(trifluormetoksi)fenil)kinolin-2-amin - (30) 8-klor-N-(3-(piperidin-1-il)propil)-N-(4-(trifluormetoksi)fenil)kinolin-2-amin - (31) 8-klor-N-(2-morfolinoetil)-N-(4-(trifluormetoksi)fenil)kinolin-2-amin - (32) 8-klor-N-(2-(pirolidin-1-il)etil)-N-(4-(trifluormetoksi)fenil)kinolin-2-amin - (33) 8-klor-N-(4-morfolinobutil)-N-(4-(trifluormetoksi)fenil)kinolin-2-amin - (34) 8-klor-N4-(3-(piperidin-1-il)propil)-N2-(4-(trifluormetoksi)fenil)kinolin-2,4-diamin - (35) 4,8-diklor-N-(4-(trifluormetoksi)fenil)kinolin-2-amin - (36) 8-klor-5-(2-morfolinoetoksi)-N-(4-(trifluormetoksi)fenil)kinolin-2-amin - (37) N1-(4,8-diklorkinolin-2-il)-4-(trifluormetoksi)benzen-1,2-diamin - (38) 4,8-diklor-N-(2-morfolinoetil)-N-(4-(trifluormetoksi)fenil)kinolin-2-amin - (39) 8-klor-6-(2-morfolinoetoksi)-N-(4-(trifluormetoksi)fenil)kinolin-2-amin - (40) 8-klor-N2-(2-morfolinoetil)-N4-(3-(piperidin-1-il)propil)-N2-(4-(trifluormetoksi)fenil)kinolin-2,4-diamin - (41) 8-klor-N-(2-morfolinoetil)-N-(2-nitro-4-(trifluormetoksi)fenil)kinolin-2-amin - (42) N1-(8-klorkinolin-2-il)-N1-(2-morfolinoetil)-4-(trifluormetoksi)benzen-1,2-diamin - (43) 8-klor-5-(2-morfolinoetoksi)-N-(2-morfolinoetil)-N-(4-(trifluormetoksi)fenil)kinolin-2-amin - (44) N1-(8-klor-5-(2-morfolinoetoksi)kinolin-2-il)-4-(trifluormetoksi)benzen-1,2-diamin - (46) 8-klor-2-((4-(trifluormetil)piridin-2-il)oksi)kinolin - (47) 4-(2-((8-klor-2-((4-(trifluormetil)piridin-2-il)oksi)kinolin-6-il)oksi)etil)morfolin - (48) 8-klor-2-(4-(trifluormetoksi)fenoksi)kinolin - (49) 4-(2-((8-klor-2-(4-(trifluormetoksi)fenoksi)kinolin-6-il)oksi)etil)morfolin - (50) 4-(2-((8-klor-2-(4-(trifluormetoksi)fenoksi)kinolin-5-il)oksi)etil)morfolin - (51) mono-[8-klor-2-(4-trifluormetil-piridin-2-ilamino)-kinolin-6-il] ester fosforne kiseline - (52) mono-[2-(8-klor-kinolin-2-ilamino)-5-trifluormetoksi-fenil] ester fosforne kiseline - (53) mono-[8-klor-2-(4-trifluormetoksi-fenilamino)-kinolin-6-il] ester fosforne kiseline - i njihove farmaceutski prihvatljive soli, i točnije odabrane između spojeva (8), (9); (10); (11); (30); (46); (47) ; (48) ; (49) i (50) kako je gore definirano ili jedna od njihovih farmaceutskih soli.
10. Spoj prema bilo kojem od patentnih zahtjeva 1 do 5, naznačen time što se koristi u liječenju, smanjenju vjerojatnosti razvoja, ili odgađanju pojave navedene upalne bolesti.
11. Spoj za upotrebu prema bilo kojem od patentnih zahtjeva 1 do 4, naznačen time što je navedena upalna bolest odabrana s popisa koji se sastoji od: upalne bolesti crijeva, Crohnove bolesti, ulceroznog kolitisa, multiple skleroze, osteoartritisa, ankilozirajućeg spondilitisa, psorijaze, Sjogrenovog sindroma, bronhitisa, i upale povezane s karcinomom debelog crijeva, a naročito je upalna bolest crijeva, Crohnova bolest, ulcerozni kolitis i multipla skleroza, te još točnije upalna bolest crijeva i multipla skleroza.
12. Spoj (Id) kako je definiran u patentnom zahtjevu 7 ili jedan od spojeva odabranih od spojeva (8), (9), (10), (11), (44), (46), (47), (48) , (49), (50), (51), (52), (53) ili njihove farmaceutski prihvatljive soli, naznačen time što je za upotrebu kao lijek.
13. Farmaceutski pripravak naznačen time što sadrži najmanje jedan spoj formule (Id) kako je definiran u zahtjevu 7 ili jedan od spojeva odabranih od spojeva (8), (9), (10), (11), (13), (14), (15), (16), (17), (18), (19), (20), (21), (22), (28), (29), (30), (31), (32 ), (33), (34), (35), (36), (37), (38), (39), (40), (41), (42), (43), (44), (46), (47), (48), (49), (50), (51), (52) i (53) i točnije jedan od spojeva (8), (9); (10); (11); (30); (46); (47) ; (48) ; (49) i (50) kako je definirano u zahtjevu 9.
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