SI2824100T1 - 1,2,5-oksadiazoli kot inhibitorji indolamine 2,3-dioksigenaze - Google Patents

1,2,5-oksadiazoli kot inhibitorji indolamine 2,3-dioksigenaze Download PDF

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SI2824100T1
SI2824100T1 SI200931815T SI200931815T SI2824100T1 SI 2824100 T1 SI2824100 T1 SI 2824100T1 SI 200931815 T SI200931815 T SI 200931815T SI 200931815 T SI200931815 T SI 200931815T SI 2824100 T1 SI2824100 T1 SI 2824100T1
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amino
oxadiazole
cancer
carboximidamide
hydroxy
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Andrew P. Combs
Eddy W. Yue
Richard B. Sparks
Wenyu Zhu
Jiacheng Zhou
Qiyan Lin
Lingkai Weng
Tai-Yuen Yue
Pingli Liu
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Incyte Holdings Corporation
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Claims (21)

1. Spojina s formulo I:
ali njena farmacevtsko sprejemljiva sol, v kombinaciji s protitelesom anti-PD-1 za uporabo v zdravljenju raka; kjer: R1 predstavlja NH2 ali CH3; R2 je Cl, Br, CF3, CH3, ali CN; R3 je H ali F; in nje enako 1 ali 2.
1,2,5-oksadiazoli kot inhibitorji indolamine 2,3-dioksigenaze Patentni zahtevki
2. Spojina ali sol za uporabo po zahtevku 1 kjer: (a) R1 predstavlja NH2; ali (b) R1 je CH3.
3. Spojina ali sol za uporabo po kateremkoli zahtevku od 1 do 2, kjer: (a) R2 predstavlja Cl; ali (b) R2 je Br; ali (c) R2 je CF3; ali (d) R2 je CH3; ali; (e) R2 je CN.
4. Spojina ali sol za uporabo po kateremkoli zahtevku od 1 do 3, kjer: -3 (a) R predstavlja H; ali (b) R3 je F.
5. Spojina ali sol za uporabo po kateremkoli zahtevku od 1 do 4, kjer: (a) jen enako 1; ali (b) n je enako 2.
6. Spojina izbrana iz skupine, ki vsebuje: 4-({2-[(aminosulfonil)amino]etil[amino)-N-(3-bromo-4-fluorofenil)-N’-hidroksi-1,2,5-oksadiazol-3-karboksimidamid; N-(3 -bromo-4-fluorofenil)-N’ -hidroksi-4-( {2- [(metilsulfonil)amino]etil} amino)- 1.2.5- oksadiazol-3 -karboksimidamid; 4-({3-[(amino sulfoniljamino] propil} amino)-N-(3 -bromo-4-fluorofenil)-N ’ -hidroksi-1,2,5-oksadiazol-3 -karboksimidamid; N-(3-bromo-4-fluorofenil)-N’-hidroksi-4-({3- [(metilsulfonil)amino]propil}amino)-l,2,5-oksadiazol-3 -karboksimidamid; 4-( {2- [(aminosulfonil)amino] etil} amino)-N-(3 -kloro-4-fluorofenil)-N’ -hidroksi- 1.2.5- oksadiazol-3 -karboksimidamid; N-(3-kloro-4-fluorofenil)-N’-hidroksi-4-({2-[(metilsulfonil)amino]etil}amino)- 1.2.5- oksadiazol-3 -karboksimidamid; 4-( {3 - [(aminosulfonil)amino]propil} amino)-N-(3 -kloro-4-fluorofenil)-N’ -hidroksi-1,2,5-oksadiazol-3 -karboksimidamid; N-(3-kloro-4-fluorofenil)-N’-hidroksi-4-({3-[(metilsulfbnil)amino]propil} amino)-1,2,5-oksadiazol-3 -karboksimidamid; 4-({2-[(aminosulfonil)amino]etil}amino)-N-[4-fluoro-3-(trifluorometil)fenil]- N’-hidroksi-l,2,5-oksadiazol-3-karboksimidamid; N-[4-fluoro-3-(trifluorometil)fenil]-N,-hidroksi-4-({2-[(metilsulfonil)amino] etil} -amino)-1 ,2,5-oksadiazol-3 -karboksimidamid; 4-( {3 - [(aminosulfonil)amino]propil} amino)-N- [4-fluoro-3 -(trifluorometil)fenil]-N’-hidroksi-l,2,5-oksadiazol-3-karboksimidamid; N - [4-fluoro-3 -(trifluorometil)fenil]-N’ -hidroksi-4-( {3 -[(metilsulfonil)amino] propil} -amino)-1,2,5-oksadiazol-3-karboksimidamid; 4-({2-[(aminosulfonil)amino]etil}amino)-N’-hidroksi-N-[3-(trifluorometil)fenil] -1,2,5-oksadiazol-3 -karboksimidamid; N’-hidroksi-4-({2-[(metilsulfonil)amino]etil}amino)-N-[3-(trifluorometil)fenil]- 1.2.5- oksadiazol-3 -karboksimidamid; 4-( {3 - [(amino sulfonil)amino] propil} amino)-N’ -hidroksi-N- [3 -(trifluorometil) fenil] -1,2,5-oksadiazol-3-karboksimidamid; N’ -hidroksi-4-( {3-[(metilsulfonil)amino]propil} amino)-N-[3-(trifluorometil) fenil]-1,2,5-oksadiazol-3-karboksimidamid; N-(4-fhioro-3-metilfenil)-N’-hidroksi-4-({2-[(metilsulfonil)amino]etil}amino)- 1.2.5- oksadiazol-3-karboksimidamid; 4-({2-[(aminosulfonil)amino]etil}amino)-N-(3-ciano-4-fluorofenil)-N,-hidroksi- 1.2.5- oksadiazol-3-karboksimidamid; in N-(3 -ciano-4-fluorofenil)-N ’ -hidroksi-4-( {2- [(metilsulfonil)amino]etil} amino)- 1.2.5- oksadiazol-3-karboksimidamid; ali njena farmacevtsko sprejemljiva sol, v kombinaciji s protitelesom anti-PD-1 za uporabo po zahtevku 1.
7. 4-({2-[(aminosulfonil)amino]etil}amino)-N-(3-bromo-4-fluorofenil)-N’-hidroksi-l,2,5-oksadiazol-3-karboksimidamid, ali njena farmacevtsko sprejemljiva sol, v kombinaciji s protitelesom anti-PD-1 za uporabo po zahtevku 1.
8. 4-( {2- [(aminosulfonil)amino] etil} amino)-N-(3 -bromo-4-fluorofenil)-N ’ -hidroksi-l,2,5-oksadiazol-3-karboksimidamid, v kombinaciji s protitelesom anti-PD-1 za uporabo po zahtevku 1.
9. Spojina ali sol za uporabo po zahtevku 1, kjer je spojina trdna oblika 4-({2-[(aminosulfonil)amino]etil}amino)-N-(3-bromo-4-fluorofenil)-N’-hidroksi- 1.2.5- oksadiazol-3-karboksimidamida, ki je: (a) kristalinična; ali (b) vsebuje manj kot 2 % vode.
10. Spojina ali sol za uporabo po zahtevku 9, kjer ima trdna oblika tališče od 162°C do 166 °C, ±3°C.
11. Spojina ali sol za uporabo po zahtevku 9, kjer ima trdna oblika: (a) vsaj en vrh XRPD, v smislu 2-theta, izbran izmed 18.4° ±0.2°, 18.9° ±0.2°, 21.8° ±0.2°, 23.9° ±0.2°, 29.2° ±0.2° in 38.7° ±0.2°; ali (b) vsaj dva vrha XRPD, v smislu 2-theta, izbrana izmed 18.4° ±0.2°, 18.9° ±0.2°, 21.8° ±0.2°, 23.9° ±0.2°, 29.2° ±0.2° in 38.7° ±0.2°; ali (c) vsaj tri vrhove XRPD, v smislu 2-theta, izbrane izmed 18.4° ±0.2°, 18.9° ±0.2°, 21.8° ±0.2°, 23.9° ±0.2°, 29.2° ±0.2° in 38.7° ±0.2°.
12. Spojina s formulo F28:
ali njena farmacevtsko sprejemljiva sol, v kombinaciji s protitelesom anti-PD-1 za uporabo v zdravljenju raka, kjer: R4 predstavlja F, Cl, Br ali I; in nje enako 1 ali 2.
13. 4-({2-[(aminosulfonil)amino]etil}amino)-N-[(4-bromo-2-furil)metil]-N’-hidroksi-l,2,5-oksadiazol-3-karboksimidamid ali njegova farmacevtsko sprejemljiva sol, v kombinaciji s protitelesom anti-PD-1 za uporabo po zahtevku 12.
14. 4-({2-[(aminosulfonil)amino]etil}amino)-N-[(4-kloro-2-furil)metil]-N’-hidroksi- l,2,5-oksadiazol-3-karboksimidamid ali njegova farmacevtsko sprejemljiva sol, v kombinaciji s protitelesom anti-PD-1 za uporabo po zahtevku 12.
15. Spojina, sil ali trdna oblika za uporabo po kateremkoli zahtevku od 1 do 12, kjer je omenjeni rak izbran iz skupine, ki vsebuje melanom, črevesni rak, rak trebušne slinavke, rak dojke, rak prostate, pljučni rak, možganski rak, rak jajčnikov, rak materničnega vratu, rak testisa, ledvični rak, rak glave in vratu, limfom in levkemijo.
16. Spojina, sol ali trdna oblika za uporabo po kateremkoli zahtevku od 7 do 11, kjer je omenjeni rak melanom.
17. Spojina, sol ali trdna oblika za uporabo po kateremkoli zahtevku od 7 do 13, kjer je omenjeni rak rak jajčnikov.
18. Spojina, sol ali trdna oblika za uporabo po kateremkoli zahtevku od 7 do 13, kjer je omenjeni rak rak dojke.
19. Spojina, sol ali trdna oblika za uporabo po kateremkoli zahtevku od 7 do 11, kjer je omenjeni rak rak trebušne slinavke.
20. Spojina, sol ali trdna oblika za uporabo po kateremkoli zahtevku od 7 do 11, kjer je omenjeni rak rak prostate.
21. Spojina, sol ali trdna oblika za uporabo po kateremkoli zahtevku od 7 do 11, kjer je rak pljučni rak.
SI200931815T 2008-07-08 2009-07-07 1,2,5-oksadiazoli kot inhibitorji indolamine 2,3-dioksigenaze SI2824100T1 (sl)

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