HRP20161367T1 - Spojevi reverznog amida kao inhibitori protein deacetilaze i postupci za njihovu uporabu - Google Patents
Spojevi reverznog amida kao inhibitori protein deacetilaze i postupci za njihovu uporabu Download PDFInfo
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- HRP20161367T1 HRP20161367T1 HRP20161367TT HRP20161367T HRP20161367T1 HR P20161367 T1 HRP20161367 T1 HR P20161367T1 HR P20161367T T HRP20161367T T HR P20161367TT HR P20161367 T HRP20161367 T HR P20161367T HR P20161367 T1 HRP20161367 T1 HR P20161367T1
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- 102000003964 Histone deacetylase Human genes 0.000 title claims 2
- 108090000353 Histone deacetylase Proteins 0.000 title claims 2
- -1 amide compounds Chemical class 0.000 title claims 2
- 239000003112 inhibitor Substances 0.000 title 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 31
- 150000001875 compounds Chemical class 0.000 claims 28
- 125000000217 alkyl group Chemical group 0.000 claims 26
- 125000003118 aryl group Chemical group 0.000 claims 20
- 125000003710 aryl alkyl group Chemical group 0.000 claims 12
- 125000003107 substituted aryl group Chemical group 0.000 claims 12
- 125000000547 substituted alkyl group Chemical group 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 10
- 125000001188 haloalkyl group Chemical group 0.000 claims 9
- 150000002148 esters Chemical class 0.000 claims 7
- 125000004076 pyridyl group Chemical group 0.000 claims 7
- 125000004452 carbocyclyl group Chemical group 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 5
- 125000001475 halogen functional group Chemical group 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 3
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- 125000001624 naphthyl group Chemical group 0.000 claims 3
- HTMGQIXFZMZZKD-UHFFFAOYSA-N 5,6,7,8-tetrahydroisoquinoline Chemical compound N1=CC=C2CCCCC2=C1 HTMGQIXFZMZZKD-UHFFFAOYSA-N 0.000 claims 2
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Claims (24)
1. Spoj formule I:
[image]
ili njegova farmaceutski prihvatljiva sol ili ester, u kojem,
Z je N ili CR*, gdje R* je izborno supstituirani alkil, izborno supstituirani acil, izborno supstituirani aril ili izborno supstituirani heteroaril;
prsten A je izborno supstituirani aril ili izborno supstituirani heteroaril;
prsten B je izborno supstituirani aril ili izborno supstituirani heteroaril;
R1 je (i) H, alkil, haloalkil, alkenil, aril, arilalkil, heteroaril, heterociklil, karbociklil, C(O)-R2, C(O)O-R2, ili S(O)p, od kojih svaki može biti izborno supstituiran; ili (ii) kada je Z jednako CR*, R1 može biti izborno supstituirani razgranati alkil, OR3, ili N(R3)(R3)-CH2CH2OH, OCH2CH2OH, SH, ili tio alkoksi;
R je H ili izborno supstituirani alkil; svako R2 je nezavisno alkil, cikloalkil, heterocikloalkil, aril ili heteroaril, od kojih je svaki izborno supstituiran;
svaki R3 je nezavisno alkil, cikloalkil, heterocikloalkil, aril ili heteroaril, od kojih je svaki izborno supstituiran;
n je 4, 5, 6, 7 ili 8; i
p je 0, 1 ili 2.
2. Spoj prema patentnom zahtjevu 1, naznačen time što prsten A je fenil, naftil, antracenil, piridinil, pirimidinil, pirazinil, indolil, imidazolil, oksazolil, furil, tienil, tiazolil, triazolil, izoksazolil, hinolinil, pirolil, pirazolil ili 5,6,7,8-tetrahidroizohinolin;
od kojih svaki može biti izborno supstituiran ili
gdje prsten B je fenil, naftil, antracenil, piridinil, pirimidinil, pirazinil, indolil, imidazolil, oksazolil, furil, tienil, tiazolil, triazolil, izoksazolil, hinolinil, pirolil, pirazolil ili 5,6,7,8-tetrahidroizohinolin; od kojih svaki može biti izborno supstituiran ili
gdje R1 je OH, alkoksi, NH2, NH(alkil), N(alkil)(alkil), NH-aril, NH-hetroaril, N(aril)(aril), N(aril)(heteroaril) ili N(heteroaril)(heteroaril).
3. Spoj prema patentnom zahtjevu 1, naznačen time što R1 je H, izborno supstituirani alkil, izborno supstituirani aril ili izborno supstituirani heteroaril, ili R1 je OH ili alkoksi, poželjno gdje R1 je H, metil, etil, propil, i-propil, butil, i-butil, t-butil, pentil, heksil, fenil, naftil, piridinil, OH ili OCH3; od kojih svaki može biti izborno supstituiran.
4. Spoj prema patentnom zahtjevu 1, naznačen time što su karbonil i Z grupa vezani za prsten A postavljeni u para međusoban položaj ili time što su karbonil i Z grupa vezani za prsten A postavljeni u meta međusobni položaj ili time što su karbonil i Z grupa vezani za prsten A postavljeni u orto međusobni položaj.
5. Spoj prema patentnom zahtjevu 1, formule II:
[image]
ili njegova farmaceutski prihvatljiva sol ili ester,
u kojem,
svako od X1, X2, X3 ili X4 je nezavisno N, CR’, O, S, NCR’, CR’CR’, OCR’, SCR’; ili je odsutan gdje do tri od X1, X2, X3 ili X4 mogu biti N;
prsten B je izborno supstituiran aril ili izborno supstituiran heteroaril;
R1 je H, alkil, haloalkil, alkenil, aril, arilalkil, heteroaril, heterociklil, karbociklil, C(O)-R2 ili C(O)O-R2 od kojih svaki može biti izborno supstituiran;
R je H ili izborno supstituiran alkil;
svaki R’ je nezavisno H, izborno supstituirani alkil, halo, OH, NH2, NHR", haloalkil, CN, N3, NO2;
R" je H ili alkil; i
R2 je alkil, cikloalkil, heterocikloalkil, aril ili heteroaril, od kojih svaki je izborno supstituiran.
6. Spoj prema patentnom zahtjevu 5, naznačen time što X1, X2, X3 i X4 su svi CR’, ili gdje X2 i X3 su N i X1 i X4 su CR’, ili
gdje X2 i X3 su CR’ i X1 i X4 su N, ili
gdje X2 je N; X3 je S, N ili O; X1 je CR’ i X4 je odsutan, ili
gdje R1 je H, alkil, aril, arilalkil ili heteroaril, od kojih svaki može biti izborno supstituiran.
7. Spoj prema patentnom zahtjevu 5, naznačen time što prsten B je fenil, piridinil, pirimidinil ili pirazinil; od kojih svaki može biti izborno supstituiran, poželjno gdje je prsten B supstituiran sa alkil, aril, heteroaril, cikloalkil, heterocikloalkil, aralkil, haloalkil, hal, OH, NH2, NHR", CN, N3 ili NO2.
8. Spoj prema patentnom zahtjevu 1, formule III:
[image]
ili njegova farmaceutski prihvatljiva sol ili ester, u kojem,
prsten B je izborno supstituirani aril ili izborno supstituirani heteroaril;
R1 je H, alkil, haloalkil, alkenil, aril, arilalkil, heteroaril, heterociklil, karbociklil, C(O)-R2 ili C(O)O-R2,
od kojih svaki može biti izborno supstituiran;
R2 je izborno supstituirani heteroaril, i
R je H ili izborno supstituirani alkil.
9. Spoj prema patentnom zahtjevu 8, naznačen time što prsten B je fenil, piridinil, pirimidinil ili pirazinil; od kojih svaki može biti izborno supstituiran, poželjno gdje je prsten B supstituiran sa alkil, aril, aralkil, haloalkil, hal, OH, NH2, CN ili NO2.
10. Spoj prema patentnom zahtjevu 8, naznačen time što R1 je H, alkil, aril, arilalkil, heteroaril, C(O)-R2 ili C(O)O-R2, od kojih svaki može biti izborno supstituiran, poželjno gdje R2 je izborno supstituirani piridinil.
11. Spoj prema patentnom zahtjevu 1, formule IV:
[image]
ili njegova farmaceutski prihvatljiva sol ili ester, u kojem,
prsten B je izborno supstituirani aril ili izborno supstituirani heteroaril;
R1 je H, alkil, haloalkil, alkenil, aril, arilalkil, heteroaril, heterociklil ili karbociklil, od kojih svaki može biti izborno supstituiran;
i
R je H ili izborno supstituirani alkil.
12. Spoj prema patentnom zahtjevu 11, naznačen time što prsten B je fenil, piridinil, pirimidinil ili pirazinil; od kojih svaki može biti izborno supstituiran, poželjno gdje je prsten B supstituiran sa alkil, aril, aralkil, haloalkil, halo, OH, NH2, CN ili NO2.
13. Spoj prema patentnom zahtjevu 11, naznačen time što R1 je H, alkil, aril, arilalkil ili heteroaril, od kojih svaki može biti izborno supstituiran, poželjno gdje je R1 supstituiran sa OH ili halo.
14. Spoj prema patentnom zahtjevu 11, naznačen time što spoj formule IV je
[image]
ili njegova farmaceutski prihvatljiva sol.
15. Spoj prema patentnom zahtjevu 11, naznačen time što spoj formule IV je
[image]
ili njegova farmaceutski prihvatljiva sol.
16. Spoj prema patentnom zahtjevu 11, naznačen time što spoj formule IV je
[image]
ili njegova farmaceutski prihvatljiva sol.
17. Spoj prema patentnom zahtjevu 1, formule VI:
[image]
ili njegova farmaceutski prihvatljiva sol ili ester, u kojem,
prsten B je izborno supstituirani aril ili izborno supstituirani heteroaril;
R* je izborno supstituirani alkil, izborno supstituirani aril ili izborno supstituirani heteroaril;
R1 je H, alkil, aril, arilalkil, heteroaril, heterociklil, karbociklil, OH, alkoksi, NH2, NH(alkil) ili N(alkil)(alkil);
i
R je H ili izborno supstituirani alkil.
18. Spoj prema patentnom zahtjevu 1, izabran od slijedećih:
[image]
[image]
[image]
[image]
[image]
[image]
[image]
[image]
[image]
[image]
[image]
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[image]
[image]
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[image]
[image]
[image]
[image]
[image]
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[image]
i
[image]
19. Farmaceutski pripravak koji sadrži spoj prema bilo kojem od patentnih zahtjeva 1-18, ili njegov farmaceutski prihvatljiv ester ili sol, zajedno sa farmaceutski prihvatljivim nosačem.
20. Spoj prema bilo kojem od patentnih zahtjeva 1 do 18 ili farmaceutski pripravak prema patentnom zahtjevu 19 za uporabu kao lijek.
21. Spoj prema bilo kojem od patentnih zahtjeva 1 do 18 ili farmaceutski pripravak prema patentnom zahtjevu 19 za uporabu u liječenju karcinoma ili proliferativne bolesti, poželjno gdje je bolest karcinom pluća, karcinom debelog crijeva, karcinom dojke, karcinom prostate, karcinom jetre, karcinom pankreasa, karcinom mozga, karcinom bubrega, karcinom jajnika, karcinom stomaka, karcinom kože, karcinom kosti, karcinom želuca, karcinom dojke, karcinom pankreasa, gliom, gliobastom, hepatostanični karcinom, papilarni bubrežni karcinom, karcinom skvamoznih stanica glave i vrata, leukemije, limfomi, mijelomi i solidni tumori ili gdje je karcinom multipli mijelom.
22. Spoj prema bilo kojem od patentnih zahtjeva 1 do 18 ili farmaceutski pripravak prema patentnom zahtjevu 19 za uporabu u liječenju Wilson-ove bolesti, spinocerebelarne ataksije, prionske bolesti, Parkinson-ove bolesti, Huntington-ove bolesti, amiotrofne lateralne skleroze, amiloidoze, Alzheimer-ove bolesti, Alexander-ove bolesti, alkoholne bolesti jetre, cistične fibroze, Pick-ove bolesti, spinalne muskularne atrofije ili demencije sa Lewy-evim tijelima.
23. Spoj prema bilo kojem od patentnih zahtjeva 1 do 18 ili farmaceutski pripravak prema patentnom zahtjevu 19 za uporabu u liječenju reumatoidnog artritisa, osteoartritisa; reumatoidnog spondilitisa; psorijaze; post-ishemične perfuzione povrede; inflamatorne bolesti crijeva; kronične inflamatorne bolesti pluća, ekcema, astme, psorijaze, ishemije/reperfuzione povrede, ulceroznog kolitisa, akutnog respiratornog distres sindroma, psorijatičkog artritisa, infektivnog artritisa, progresivnog kroničnog artritisa, deformirajućeg artritisa, osteoartritisa, traumatskog artritisa, gihta, Reiter-ovog sindroma, polihondritisa, akutnog sinovitisa i spondilitisa, glomerulonefritisa, hemolitičke anemije, aplastične anemije, idiopatske trombocitopenije, neutropenije, ulceroznog kolitisa, Crohn-ove bolesti, bolesti transplanta protiv domaćina, odbacivanja alografta, kroničnog tiroiditisa, Graves-ove bolesti, skleroderme, dijabetesa, aktivnog hepatitisa, primarne bilijarne ciroze, miastenije gravis, multiple skleroze (MS), sustavnog lupus eritematozisa, atopijskog dermatitisa, kontaktnog dermatitisa, opeklina od sunca na koži, kronične bubrežne insuficijencije, Stevens-Johnson-ovog sindroma, idiopatskog sprue-a, sarkoidoze, Guillain-Barre-ovog sindroma, uveitisa, konjuktivitisa, keratokonjuktivitisa, otitis medije, periodontalne bolesti, plućne intersticijalne fibroze, astme, bronhitisa, rinitisa, sinusitisa, pneumokoniozisa, sindroma plućne insuficijencije, plućnog emfizema, plućne fibroze, silikoze ili kronične inflamatorne bolesti pluća.
24. Komplet koji sadrži spoj sposoban da inhibira aktivnost HDAC izabran od jednog ili više spojeva formule I:
[image]
ili njegovu farmaceutski prihvatljivu sol ili ester, u kojem,
Z je N ili CR*, gdje R* je izborno supstituirani alkil, izborno supstituirani acil, izborno supstituirani aril ili izborno supstituirani heteroaril;
prsten A je izborno supstituirani aril ili izborno supstituirani heteroaril;
prsten B je izborno supstituirani aril ili izborno supstituirani heteroaril;
R1 je (i) H, alkil, haloalkil, alkenil, aril, arilalkil, heteroaril, heterociklil, karbociklil, C(O)-R2, C(O)O-R2 ili S(O)p, od kojih svaki može biti izborno supstituiran; ili (ii) kada je Z jednako CR*, R1 može biti izborno supstituiran razgranati alkil, OR3 ili N(R3)(R3), -CH2CH2OH, OCH2CH2OH, SH ili tio alkoksi;
R je H ili izborno supstituirani alkil;
svaki R2 je nezavisno alkil, cikloalkil, heterocikloalkil, aril ili heteroaril, od kojih je svaki izborno supstituiran;
svaki R3 je nezavisno alkil, cikloalkil, heterocikloalkil, aril ili heteroaril, od kojih je svaki izborno supstituiran;
n je 4, 5, 6, 7 ili 8; i
p je 0, 1 ili 2;
i uputstva za uporabu u liječenju multiplog mijeloma.
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