HRP20171537T1 - Novi modulatori benzopiran kinaze - Google Patents
Novi modulatori benzopiran kinaze Download PDFInfo
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- HRP20171537T1 HRP20171537T1 HRP20171537TT HRP20171537T HRP20171537T1 HR P20171537 T1 HRP20171537 T1 HR P20171537T1 HR P20171537T T HRP20171537T T HR P20171537TT HR P20171537 T HRP20171537 T HR P20171537T HR P20171537 T1 HRP20171537 T1 HR P20171537T1
- Authority
- HR
- Croatia
- Prior art keywords
- amino
- chromen
- pyrazolo
- pyrimidin
- fluorophenyl
- Prior art date
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- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 title 1
- 108091000080 Phosphotransferase Proteins 0.000 title 1
- 102000020233 phosphotransferase Human genes 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 19
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 12
- 229910052736 halogen Inorganic materials 0.000 claims 10
- 150000002367 halogens Chemical group 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 4
- YZRUPFZRJYBQTF-UHFFFAOYSA-N 2-[1-[4-amino-3-(3-methyl-2h-indazol-6-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=C3NN=C(C)C3=CC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 YZRUPFZRJYBQTF-UHFFFAOYSA-N 0.000 claims 3
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- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- HLYJVSITVHYMGF-UHFFFAOYSA-N 2-[1-[4-amino-3-(3-methyl-1h-indol-6-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=C3NC=C(C)C3=CC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 HLYJVSITVHYMGF-UHFFFAOYSA-N 0.000 claims 2
- ZXRCPILJODBCHJ-NSHDSACASA-N 6-fluoro-3-(3-fluorophenyl)-2-[(1s)-1-(7h-purin-6-ylamino)ethyl]chromen-4-one Chemical compound C=1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)OC2=CC=C(F)C=C2C(=O)C=1C1=CC=CC(F)=C1 ZXRCPILJODBCHJ-NSHDSACASA-N 0.000 claims 2
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims 2
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- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 2
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims 2
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims 2
- 208000033222 Biliary cirrhosis primary Diseases 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 201000004624 Dermatitis Diseases 0.000 claims 2
- 208000035186 Hemolytic Autoimmune Anemia Diseases 0.000 claims 2
- 208000007452 Plasmacytoma Diseases 0.000 claims 2
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 2
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- 201000004681 Psoriasis Diseases 0.000 claims 2
- 206010039710 Scleroderma Diseases 0.000 claims 2
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- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims 2
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 2
- 239000000739 antihistaminic agent Substances 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 201000000448 autoimmune hemolytic anemia Diseases 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 2
- 201000001981 dermatomyositis Diseases 0.000 claims 2
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- 125000005842 heteroatom Chemical group 0.000 claims 2
- 239000003018 immunosuppressive agent Substances 0.000 claims 2
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- 125000002346 iodo group Chemical group I* 0.000 claims 2
- 208000017169 kidney disease Diseases 0.000 claims 2
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- 206010025135 lupus erythematosus Diseases 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims 2
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 150000003431 steroids Chemical class 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- AYRISEUMQZXCRR-UHFFFAOYSA-N 2-[(4-amino-3-iodopyrazolo[3,4-d]pyrimidin-1-yl)methyl]-3-phenylchromen-4-one Chemical compound N1=C(I)C=2C(N)=NC=NC=2N1CC=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 AYRISEUMQZXCRR-UHFFFAOYSA-N 0.000 claims 1
- LDLONLGMHQZNEZ-UHFFFAOYSA-N 2-[(4-amino-3-iodopyrazolo[3,4-d]pyrimidin-1-yl)methyl]-6-fluoro-3-phenylchromen-4-one Chemical compound N1=C(I)C=2C(N)=NC=NC=2N1CC=1OC2=CC=C(F)C=C2C(=O)C=1C1=CC=CC=C1 LDLONLGMHQZNEZ-UHFFFAOYSA-N 0.000 claims 1
- NTGZDSWGOWEOGR-UHFFFAOYSA-N 2-[(4-amino-3-pyridin-3-ylpyrazolo[3,4-d]pyrimidin-1-yl)methyl]-3-phenylchromen-4-one Chemical compound N1=C(C=2C=NC=CC=2)C=2C(N)=NC=NC=2N1CC=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 NTGZDSWGOWEOGR-UHFFFAOYSA-N 0.000 claims 1
- MUEWLASOJKNMNL-UHFFFAOYSA-N 2-[(4-aminopyrazolo[3,4-d]pyrimidin-1-yl)methyl]-6-bromo-3-phenylchromen-4-one Chemical compound N1=CC=2C(N)=NC=NC=2N1CC=1OC2=CC=C(Br)C=C2C(=O)C=1C1=CC=CC=C1 MUEWLASOJKNMNL-UHFFFAOYSA-N 0.000 claims 1
- YXAHXAJHKGKKHF-UHFFFAOYSA-N 2-[(6-aminopurin-9-yl)methyl]-3-(2-fluorophenyl)chromen-4-one Chemical compound C1=NC=2C(N)=NC=NC=2N1CC=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1F YXAHXAJHKGKKHF-UHFFFAOYSA-N 0.000 claims 1
- JSWRDBXIUPWLOB-UHFFFAOYSA-N 2-[(6-aminopurin-9-yl)methyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=NC=2C(N)=NC=NC=2N1CC=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 JSWRDBXIUPWLOB-UHFFFAOYSA-N 0.000 claims 1
- IEBKPGFBYUVXHF-UHFFFAOYSA-N 2-[(6-aminopurin-9-yl)methyl]-3-(4-fluorophenyl)chromen-4-one Chemical compound C1=NC=2C(N)=NC=NC=2N1CC=1OC2=CC=CC=C2C(=O)C=1C1=CC=C(F)C=C1 IEBKPGFBYUVXHF-UHFFFAOYSA-N 0.000 claims 1
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- LUGWDWISIUMJDF-UHFFFAOYSA-N 2-[(6-aminopurin-9-yl)methyl]-6-bromo-3-(2-fluorophenyl)chromen-4-one Chemical compound C1=NC=2C(N)=NC=NC=2N1CC=1OC2=CC=C(Br)C=C2C(=O)C=1C1=CC=CC=C1F LUGWDWISIUMJDF-UHFFFAOYSA-N 0.000 claims 1
- TWVTUTIJEJURNK-UHFFFAOYSA-N 2-[(6-aminopurin-9-yl)methyl]-6-bromo-3-(2-methylphenyl)chromen-4-one Chemical compound CC1=CC=CC=C1C(C(C1=CC(Br)=CC=C1O1)=O)=C1CN1C2=NC=NC(N)=C2N=C1 TWVTUTIJEJURNK-UHFFFAOYSA-N 0.000 claims 1
- CXQQTVRXULNEFK-UHFFFAOYSA-N 2-[(6-aminopurin-9-yl)methyl]-6-bromo-3-(4-fluorophenyl)chromen-4-one Chemical compound C1=NC=2C(N)=NC=NC=2N1CC=1OC2=CC=C(Br)C=C2C(=O)C=1C1=CC=C(F)C=C1 CXQQTVRXULNEFK-UHFFFAOYSA-N 0.000 claims 1
- RVTDWEOFIDCTBZ-UHFFFAOYSA-N 2-[(6-aminopurin-9-yl)methyl]-6-bromo-3-phenylchromen-4-one Chemical compound C1=NC=2C(N)=NC=NC=2N1CC=1OC2=CC=C(Br)C=C2C(=O)C=1C1=CC=CC=C1 RVTDWEOFIDCTBZ-UHFFFAOYSA-N 0.000 claims 1
- PHQZPXCGTYJFLH-UHFFFAOYSA-N 2-[(6-aminopurin-9-yl)methyl]-6-fluoro-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=NC=2C(N)=NC=NC=2N1CC=1OC2=CC=C(F)C=C2C(=O)C=1C1=CC=CC(F)=C1 PHQZPXCGTYJFLH-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/34—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 3 only
- C07D311/36—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 3 only not hydrogenated in the hetero ring, e.g. isoflavones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/34—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 3 only
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C07D473/08—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1 and 3, e.g. theophylline
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Claims (16)
1. Spoj s formulom (IA-I), (IA-II), (IA-III), ili (IA-IV):
[image]
ili njegov tautomer, njegov N-oksid, ili njegova farmaceutski prihvatljiva sol, naznačen time da
svaka pojava za R je neovisno odabrana iz niza koji sadrži vodik, halogen, -ORa, CN, supstituiran ili nesupstituiran C1-6 alkil, supstituiran ili nesupstituiran C2-6 alkenil, supstituiran ili nesupstituiran C2-6 alkinil, supstituiran ili nesupstituiran C3-8 cikloalkil, i supstituiranu ili nesupstituiranu heterocikličku skupinu;
R1 i R2 mogu biti isti ili različiti i neovisno su odabrani iz niza koji sadrži vodik, halogen, i supstituiran ili nesupstituiran C1-6 alkil, ili oba R1 i R2 izravno vezani na zajednički atom, se mogu spojiti tako da tvore okso skupinu (=O) ili supstituirani ili nesupstituirani zasićeni ili nezasićeni 3-10 člani prsten (uključujući ugljikov atom na koji su vezani R1 i R2), koji po potrebi može sadržavati jedan ili više heteroatoma koji mogu biti isti ili različiti i odabrani su od O, NRa i S;
Cy1 je monociklička skupina izabrana od supstituiranog ili nesupstituiranog cikloalkila, supstituirane ili nesupstituirane heterocikličke skupine, i supstituiranog ili nesupstituiranog arila i supstituiranog ili nesupstituiranog heteroarila;
svaka pojava za Ra može biti ista ili različita i neovisno je odabrana od vodika, halogena, hidroksi, cijano, supstituiranog ili nesupstituiranog (C1-6)alkila, -NRcRd (pri čemu Rc i Rd su neovisno vodik, halogen, hidroksi, cijano, supstituiran ili nesupstituiran (C1-6)alkil, i (C1-6)alkoksi) i - ORc (pri čemu Rc je supstituiran ili nesupstituiran (C1-6)alkil);
n je cijeli broj od 1 do 4; i
q je 0, 1 ili 2,
svaka pojava za X je neovisno odabrana od CR3 ili N, pri čemu R3 je vodik, hidroksi, halogen, -NH2, jodo, cijano, supstituiran ili nesupstituiran alkil, supstituiran ili nesupstituiran alkinil, supstituiran ili nesupstituiran aril, ili supstituiran ili nesupstituiran heteroaril; i
pri čemu se izraz supstituiran odnosi na supstituciju koju se bira iz skupa koji čine vodik, hidroksi, halogen, karboksil, cijano, nitro, okso (=O), tio(=S), supstituiran ili nesupstituiran alkil, supstituiran ili nesupstituiran alkoksi, supstituiran ili nesupstituiran alkenil, supstituiran ili nesupstituiran alkinil, supstituiran ili nesupstituiran cikloalkil, supstituiran ili nesupstituiran cikloalkenil, -COORx, -C(O)Rx, -C(S)Rx, -C(O)ONRxRy, -NRxCONRyRz, - N(Rx)SORy, -N(Rx)S02Ry, -(=N-N(Rx)Ry), -NRx C(O)ORy, -NRxRy, -NRxC(O)Ry-, - RxC(S)Ry -NRxC(S)NRyRz, -SONRxRy-, -SO2 NRxRy-, -ORx, -ORxC(O)NRyRZ, - ORxC(O)ORy-, -OC(O)Rx, -OC(O)NRxRy, -RxNRyC(O)Rz, -RxORy, -RxC(O)ORy, - RxC(O)NRyRz, -RxC(O)Rx, -RxOC(O)Ry, -SRx, -SORx, -SO2Rx, i -ONO2, pri čemu Rx, Ry i Rz u svakoj od gore navedenih skupina mogu biti vodikov atom, supstituiran ili nesupstituiran alkil, supstituiran ili nesupstituiran alkoksi, supstituiran ili nesupstituiran alkenil, supstituiran ili nesupstituiran alkinil, supstituiran ili nesupstituiran aril, supstituiran ili nesupstituiran arilalkil, supstituiran ili nesupstituiran cikloalkil, supstituiran ili nesupstituiran cikloalkenil, supstituiran ili nesupstituiran amino, supstituiran ili nesupstituiran aril, supstituiran ili nesupstituiran heteroaril, supstituiran heterociklilalkil prsten, supstituiran ili nesupstituiran heteroarilalkil, supstituiran ili nesupstituiran heterociklički prsten, ili bilo koja dva od Rx, Ry i Rz zajedno sa zajedničkim atomom na koji su vezani se mogu spojiti tako da tvore supstituirani ili nesupstituirani zasićeni ili nezasićeni 3-10 člani prsten, koji po izboru može uključivati heteroatome koji mogu biti isti ili različiti i odabrani su od O, NRX ili S pri čemu supstituenti u gore spomenutim "supstituiranim" skupinama ne mogu biti dalje supstituirani.
2. Spoj prema zahtjevu 1, naznačen time da spoj ima formulu (IA-V)
[image]
ili njegova farmaceutski prihvatljiva sol,
pri čemu
R, R1, R2, R3 i X su kako je definirano u zahtjevu 1;
svaka pojava za R5 je vodik, C1-6 alkil ili halogen;
n je 0, 1, 2, 3 ili 4; i
p je 0, 1, 2, 3, 4 ili 5.
3. Spoj prema zahtjevu 1, naznačen time da spoj ima formulu (IA-VI):
[image]
ili njegova farmaceutski prihvatljiva sol, pri čemu
R, R1, R2 i X su kako je definirano u zahtjevu 1;
svaka pojava za R5 je vodik, C1-6 alkil ili halogen;
n je 0, 1, 2, 3 ili 4; i
p je 0, 1, 2, 3, 4 ili 5.
4. Spoj prema bilo kojem od zahtjeva 1-3, naznačen time da R je vodik, halogen, supstituiran ili nesupstituiran C1-6 alkil, ili ORa.
5. Spoj prema zahtjevu 4, naznačen time da Ra je alkil.
6. Spoj prema zahtjevu 1, naznačen time da Cy1 je odabran od:
[image]
7. Spoj prema bilo kojem od zahtjeva 1-6, naznačen time da R1 i R2 predstavljaju vodik ili supstituiran ili nesupstituiran C1-6 alkil.
8. Spoj prema bilo kojem od zahtjeva 1-3, naznačen time da R3 je jodo, cijano, supstituiran ili nesupstituiran alkil, supstituiran ili nesupstituiran alkinil, supstituiran ili nesupstituiran aril, ili supstituiran ili nesupstituiran heteroaril.
9. Spoj prema bilo kojem od zahtjeva 1-3, naznačen time da X je CR3 i svaka pojava za R3 je neovisno vodik, halogen, hidroksil ili NH2.
10. Spoj prema zahtjevu 9, naznačen time da R3 je vodik.
11. Spoj prema bilo kojem od zahtjeva 1-3, naznačen time da je spoj odabran iz niza koji čine:
2-[(6-amino-9H-purin-9-il)metil]-6-bromo-3-fenil-4H-kromen-4-on;
2-[(6-amino-9H-purin-9-il)metil]-3-fenil-4H-kromen-4-on;
2-((9H-purin-6-iltio)metil)-3-fenil-4H-kromen-4-on;
2-[(9H-purin-6-iltio)metil]-6-bromo-3-fenil-4H-kromen-4-on;
2-((4-amino-1H-pirazolo[3,4-d]pirimidin-1-il)metil)-6-bromo-3-fenil-4H-kromen-4-on;
2-[(6-amino-9H-purin-9-il)metil]-6-bromo-3-(4-fluorofenil)-4H-kromen-4-on;
2-[(6-amino-9H-purin-9-il)metil]-3-(4-fluorofenil)-4H-kromen-4-on;
2-(1-(6-amino-9H-purin-9-il)etil)-6-bromo-3-fenil-4H-kromen-4-on;
2-(1-(9H-purin-6-iltio)etil)-6-bromo-3-fenil-4H-kromen-4-on;
2-(1-(6-amino-9H-purin-9-il)etil)-3-fenil-4H-kromen-4-on;
(S)-2-(1-(9H-purin-6-ilamino)etil)-6-bromo-3-fenil-4H-kromen-4-on;
2-((9H-purin-6-ilamino)metil)-6-bromo-3-fenil-4H-kromen-4-on;
2-(1-(4-amino-1H-pirazolo[3,4-d]pirimidin-1-il)etil)-6-bromo-3-fenil-4H-kromen-4-on;
2-((6-amino-9H-purin-9-il)metil)-6-metoksi-3-fenil-4H-kromen-4-on;
2-(1-(6-amino-9H-purin-9-il)etil)-6-bromo-3-(2-fluorofenil)-4H-kromen-4-on;
2-((6-amino-9H-purin-9-il)metil)-6-bromo-3-(2-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-1H-pirazolo[3,4-d]pirimidin-1-il)etil)-3-fenil-4H-kromen-4-on;
2-(1-(6-amino-9H-purin-9-il)propil)-3-fenil-4H-kromen-4-on;
2-(1-(6-amino-9H-purin-9-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-((6-amino-9H-purin-9-il)metil)-3-(2-fluorofenil)-4H-kromen-4-on;
2-(1-(6-amino-9H-purin-9-il)etil)-3-(2-fluorofenil)-4H-kromen-4-on;
2-(1-(6-amino-9H-purin-9-il)propil)-3-(2-fluorofenil)-4H-kromen-4-on;
2-(1-(6-amino-9H-purin-9-il)propil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(6-amino-9H-purin-9-il)propil)-3-(4-fluorofenil)-4H-kromen-4-on;
2-(1-(6-amino-9H-purin-9-il)propil)-6-fluoro-3-fenil-4H-kromen-4-on;
2-(1-(6-amino-9H-purin-9-il)etil)-3-(4-fluorofenil)-4H-kromen-4-on;
2-(1-(6-amino-9H-purin-9-il)etil)-6-fluoro-3-fenil-4H-kromen-4-on;
2-(1-(4-amino-3-(3-metoksifenil)-1H-pirazolo[3,4-d]pirimidin-1-il)etil)-3-fenil-4H-kromen-4-on;
2-(1-(4-amino-3-(3-hidroksifenil)-1H-pirazolo[3,4-d]pirimidin-1-il)etil)-3-fenil-4H-kromen-4-on;
2-((9H-purin-6-ilamino)metil)-3-fenil-4H-kromen-4-on;
2-(1-(6-amino-9H-purin-9-il)etil)-3-o-tolil-4H-kromen-4-on;
2-((9H-purin-6-ilamino)metil)-3-(2-fluorofenil)-4H-kromen-4-on;
2-((9H-purin-6-ilamino)metil)-3-(3-fluorofenil)-4H-kromen-4-on;
(S)-2-(1-(9H-purin-6-ilamino)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(6-amino-9H-purin-9-il)etil)-6-fluoro-3-(2-fluorofenil)-4H-kromen-4-on;
2-(1-(6-amino-9H-purin-9-il)etil)-3-(3,5-difluorofenil)-4H-kromen-4-on;
2-(1-(6-amino-9H-purin-9-il)etil)-6-fluoro-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(3-metoksifenil)-1H-pirazolo[3,4-d]pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(3-hidroksifenil)-1H-pirazolo[3,4-d]pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-((4-amino-3-(3-metoksifenil)-1H-pirazolo[3,4-d]pirimidin-1-il) metil)-3-fenil-4H-kromen-4-on;
2-((4-amino-3-(3-hidroksifenil)-1H-pirazolo[3,4-d]pirimidin-1-il) metil)-3-fenil-4H-kromen-4-on;
2-((4-amino-3-(3-metoksifenil)-1H-pirazolo[3,4-d]pirimidin-1-il) metil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-((4-amino-3-(3-hidroksifenil)-1H-pirazolo [3,4-d] pirimidin-1-il) metil)-3-(3-fluorofenil)-4H-kromen-4-on;
(R)-2-(1-(9H-purin-6-ilamino)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
(S-2-(1-(9H-purin-6-ilamino)etil)-6-fluoro-3-fenil-4H-kromen-4-on;
2-((4-amino-3-jodo-1H-pirazolo[3,4-d]pirimidin-1-il) metil)-3-fenil-4H-kromen-4-on;
2-(1-(4-amino-3-jodo-1H-pirazolo[3,4-d]pirimidin-1-il)etil)-3-fenil-4H-kromen-4-on;
2-(1-(4-amino-3-jodo-1H-pirazolo[3,4-d]pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-((4-amino-3-jodo-1H-pirazolo[3,4-d]pirimidin-1-il)metil)-6-fluoro-3-fenil-4H-kromen-4-on;
2-(1-(4-amino-3-jodo-1H-pirazolo[3,4-d]pirimidin-1-il)etil)-6-fluoro-3-fenil-4H-kromen-4-on;
2-(1-(4-amino-3-jodo-1H-pirazolo [3,4-d]pirimidin-1-il)etil)-6-fluoro-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-jodo-1H-pirazolo[3,4-d]pirimidin-1-il)propil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-((4-amino-3-(piridin-3-il)-1H-pirazolo[3,4-d]pirimidin-1-il) metil)-3-fenil-4H-kromen-4-on;
2-((4-amino-3-(3-hidroksiprop-1-inil)-1H-pirazolo[3,4-d]pirimidin-1-il) metil)-3-fenil-4H-kromen-4-on;
2-((4-amino-3-(1H-pirazol-4-il)-1H-pirazolo[3,4-d]pirimidin-1-il) metil)-3-fenil-4H-kromen-4-on;
2-((4-amino-3-(3-(hidroksimetil)fenil)-1H-pirazolo[3,4-d]pirimidin-1-il) metil)-3-fenil-4H-kromen-4-on;
2-((4-amino-3-(1H-indazol-4-il)-1H-pirazolo[3,4-d]pirimidin-1-il) metil)-3-fenil-4H-kromen-4-on;
2-((4-amino-3-(3-fluorofenil)-1H-pirazolo[3,4-d]pirimidin-1-il) metil)-3-fenil-4H-kromen-4-on
2-((4-amino-3-(3-hidroksipropil)-1H-pirazolo[3,4-d]pirimidin-1-il) metil)-3-fenil-4H-kromen-4-on;
N-(3-(4-amino-1-((4-okso-3-fenil-4H-kromen-2-il)metil)-1H-pirazolo [3, 4-d]pirimidin-3-il)fenil) acetamid;
2-((4-amino-3-(3-fluoro-5-metoksifenil)-1H-pirazolo[3,4-d]pirimidin-1-il)metil)-3-fenil-4H-kromen-4-on;
2-((4-amino-3-(3-fluoro-5-hidroksifenil)-1H-pirazolo[3,4-d]pirimidin-1-il)metil)-3-fenil-4H-kromen-4-on;
2-((4-amino-3-(3-fluoro-5-metoksifenil)-1H-pirazolo [3,4-d]pirimidin-1-il)metil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-((4-amino-3-(3-fluoro-5-hidroksifenil)-1H-pirazolo[3,4-d]pirimidin-1-il) metil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(1H-pirazol-4-il)-1H-pirazolo[3,4-d]pirimidin-1-il) etil)-3-fenil-4H-kromen-4-on;
2-(1-(4-amino-3-(1H-indazol-6-il)-1H-pirazolo[3,4-d]pirimidin-1-il) etil)-3-fenil-4H-kromen-4-on;
2-(1-(4-amino-3-(3-hidroksi-3-metilbut-1-inil)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-3-fenil-4H-kromen-4-on;
2-(1-(4-amino-3-(1H-pirazol-4-il)-1H-pirazolo[3,4-d]pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
(S)-2-(1-(9H-purin-6-ilamino)etil)-3-fenil-4H-kromen-4-on;
(S)-2-(1-(9H-purin-6-ilamino)etil)-6-fluoro-3-(3-fluorofenil)-4H-kromen-4-on;
2-((4-amino-3-(1H-indazol-6-il)-1H-pirazolo[3,4-d]pirimidin-1-il) metil)-3-fenil-4H-kromen-4-on;
2-(1-(4-amino-3-(3-fluoro-5-metoksifenil)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(3-fluoro-5-hidroksifenil)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(1H-indazol-4-il)-1H-pirazolo[3,4-d]pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(3,5-dimetil-1H-pirazol-4-il)-1H-pirazolo [3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(3-metil-1H-indazol-6-il)-1H-pirazolo [3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(1H-indazol-6-il)-1H-pirazolo [3,4-d] pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(2-(hidroksimetil)fenil)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(4-fluoro-3-metoksifenil)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(4-fluoro-3-hidroksifenil)-1H-pirazolo[3,4-d] pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(3-hidroksiprop-1-inil)-1H-pirazolo [3,4-d] pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(3-fluoro-4-metoksifenil)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(3-fluoro-4-hidroksifenil)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(3-kloro-5-metoksifenil)-1H-pirazolo [3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(3-kloro-5-hidroksifenil)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(3-(trifluorometoksi)fenil)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(4-metoksifenil)-1H-pirazolo[3,4-d] pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(4-hidroksifenil)-1H-pirazolo [3,4-d] pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-((6-amino-9H-purin-9-il)metil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(4-fluoro-2-metoksifenil)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(4-fluoro-2-hidroksifenil)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-((4-amino-3-(3-aminofenil)-1H-pirazolo[3,4-d] pirimidin-1-il) metil)-3-fenil-4H-kromen-4-on;
2-((4-amino-3-(3-metil-1H-indazol-6-il)-1H-pirazolo[3,4-d] pirimidin-1-il) metil)-3-fenil-4H-kromen-4-on;
2-(1-(4-amino-3-(2-aminopirimidin-5-il)-1H-pirazolo[3,4-d] pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(1H-indol-6-il)-1H-pirazolo[3,4-d] pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(4-kloro-3-metoksifenil)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(4-kloro-3-hidroksifenil)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(2-kloro-5-metoksifenil)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(2-kloro-5-hidroksifenil)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(3,4-dimetoksifenil)-1H-pirazolo[3,4-d] pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(3,4-dihidroksifenil)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-((4-amino-3-(3-metil-1H-indazol-6-il)-1H-pirazolo[3,4-d] pirimidin-1-il)metil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(1H-indol-5-il)-1H-pirazolo[3,4-d] pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(3-metil-1H-indol-5-il)-1H-pirazolo[3,4-d] pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
tert-butil-(5-(4-amino-1-(1-(3-(3-fluorofenil)-4-okso-4H-kromen-2-il) etil)-1H-pirazolo[3,4-d]pirimidin-3-il) tiofen-2-il)metilkarbamat;
2-(1-(4-amino-3-(5-(aminometil)tiofen-2-il)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-((4-amino-3-(3-metil-1H-indazol-6-il)-1H-pirazolo[3,4-d] pirimidin-1-il) metil)-6-fluoro-3-fenil-4H-kromen-4-on;
2-(1-(4-amino-3-(3-metil-1H-indazol-6-il)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-3-fenil-4H-kromen-4-on;
2-(1-(4-amino-3-(3-metil-1H-indazol-6-il)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-6-fluoro-3-fenil-4H-kromen-4-on;
2-(1-(4-amino-3-(3-metil-1H-indazol-5-il)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
N-(4-(4-amino-1-(1-(3-(3-fluorofenil)-4-okso-4H-kromen-2-il)etil)-1H-pirazolo[3, 4-d] pirimidin-3-il)fenil) acetamid;
2-(1-(4-amino-3-(4-aminofenil)-1H-pirazolo[3,4-d] pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(3-metil-1H-indazol-6-il)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-6-fluoro-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(2,3-dihidrobenzofuran-5-il)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(3-etil-1H-indazol-6-il)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(3-metil-1H-indol-6-il)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(2-metoksipirimidin-5-il)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
4-(4-amino-1-(1-(3-(3-fluorofenil)-4-okso-4H-kromen-2-il)etil)-1H-pirazolo [3, 4-d]pirimidin-3-il)tiofen-2-karbaldehid;
2-(1-(4-amino-3-(5-(hidroksimetil)tiofen-3-il)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(2-metil-1H-benzo[d]imidazol-5-il)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(3-metil-1H-indazol-6-il)-1H-pirazolo[3,4-d] pirimidin-1-il)propil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(3-metil-1H-indol-6-il)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-((6-amino-9H-purin-9-il)metil)-6-fluoro-3-fenil-4H-kromen-4-on;
2-((6-amino-9H-purin-9-il)metil)-6-fluoro-3-(3-fluorofenil)-4H-kromen-4-on;
2-((4-amino-3-(3-fluoro-5-metoksifenil)-1H-pirazolo[3,4-d] pirimidin-1-il)metil)-6-fluoro-3-(3-fluorofenil)-4H-kromen-4-on;
2-((4-amino-3-(3-fluoro-5-hidroksifenil)-1H-pirazolo[3,4-d] pirimidin-1-il)metil)-6-fluoro-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(3-metoksifenil)-1 H-pirazolo[3,4-d] pirimidin-1-il) etil)-6-fluoro-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(3-hidroksifenil)-1H-pirazolo[3,4-d] pirimidin-1-il) etil)-6-fluoro-3-(3-fluorofenil)-4H-kromen-4-on;
2-((9H-purin-6-ilamino)metil)-6-fluoro-3-(3-fluorofenil)-4H-kromen-4-on;
2-((9H-purin-6-ilamino)metil)-6-fluoro-3-fenil-4H-kromen-4-on;
(R)-2-(1-(9H-purin-6-ilamino)etil)-6-fluoro-3-(3-fluorofenil)-4H-kromen-4-on;
2-((4-amino-3-(1H-pirazol-4-il)-1H-pirazolo[3,4-d] pirimidin-1-il) metil)-6-fluoro-3-fenil-4H-kromen-4-on;
2-(1-(4-amino-3-(3,5-difluoro-4-metoksifenil)-1H-pirazolo [3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(3,5-difluoro-4-hidroksifenil)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-((4-amino-3-(3,5-difluoro-4-metoksifenil)-1H-pirazolo[3,4-d] pirimidin-1-il)metil)-6-fluoro-3-(3-fluorofenil)-4H-kromen-4-on;
2-((4-amino-3-(3,5-difluoro-4-hidroksifenil)-1H-pirazolo[3,4-d] pirimidin-1-il)metil)-6-fluoro-3-(3-fluorofenil)-4H-kromen-4-on;
(+)-2-(1-(4-amino-3-(3-metil-1H-indazol-6-il)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
(-)-2-(1-(4-amino-3-(3-metil-1H-indazol-6-il)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(3,5-dimetoksifenil)-1H-pirazolo[3,4-d]pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(4-metoksi-3, 5-dimetilfenil)-1H-pirazolo[3,4-d] pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(2-fluoro-5-izopropoksifenil)-1H-pirazolo[3,4-d] pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(2, 3-dihidrobenzo[b] [1,4] dioksin-6-il)-1H-pirazolo [3, 4-d] pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(1-benzil-1H-pirazol-4-il)-1H-pirazolo [3,4-d] pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(2-metilpiridin-4-il)-1H-pirazolo [3,4-d] pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(3,4-dihidro-2H-benzo[b][1,4]dioksepin-7-il)-1H-pirazolo[3,4-d]pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(6-morpholinopiridin-3-il)-1H-pirazolo [3,4-d] pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(dibenzo[b,d]furan-4-il)-1H-pirazolo[3,4-d]pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(4-fenoksifenil)-1H-pirazolo [3,4-d] pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(4-(benziloksi)-3-klorofenil)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(3-kloro-4-izopropoksifenil)-1H-pirazolo [3,4-d] pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(3-(dimetilamino) fenil)-1H-pirazolo [3,4-d] pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(4-etoksi-3-fluorofenil)-1H-pirazolo [3,4-d] pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(4-izopropoksifenil)-1H-pirazolo [3,4-d] pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(4-(trifluorometoksi)fenil)-1H-pirazolo [3,4-d] pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(3-(4-acetilfenil)-4-amino-1H-pirazolo [3,4-d] pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(4-(benziloksi)fenil)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(4-(dimetilamino)fenil)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(4-(metilsulfonil)fenil)-1H-pirazolo[3,4-d]pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(3-etoksifenil)-1H-pirazolo [3,4-d]pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(benzo[b]tiofen-2-il)-1H-pirazolo[3,4-d]pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(5-klorotiofen-2-il)-1H-pirazolo[3,4-d]pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(3,5-dimetilizoksazol-4-il)-1H-pirazolo[3,4-d] pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(3-propoksifenil)-1H-pirazolo [3,4-d] pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(furan-2-il)-1H-pirazolo[3,4-d]pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(4-etoksifenil)-1H-pirazolo [3,4-d] pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(3-kloro-4-metoksifenil)-1H-pirazolo[3,4-d] pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(3-fluoro-4-izopropoksifenil)-1H-pirazolo[3,4-d] pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(6-fluoropiridin-3-il)-1H-pirazolo[3,4-d]pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(pirimidin-5-il)-1H-pirazolo [3, 4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(3-(metoksimetil)fenil)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(6-hidroksinaftalen-2-il)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(3-izopropoksifenil)-1 H-pirazolo [3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(1-metil-1H-pirazol-4-il)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(1,3-dimetil-1H-indazol-6-il)-1H-pirazolo[3,4-d] pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(2,3-dimetil-2H-indazol-6-il)-1H-pirazolo[3,4-d] pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(6-metoksinaftalen-2-il)-1H-pirazolo[3,4-d] pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(benzo[b]tiofen-3-il)-1H-pirazolo[3,4-d]pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(2,4-dimetoksipirimidin-5-il)-1H-pirazolo[3,4-d] pirimidin-1-il) etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(6-etoksinaftalen-2-il)-1H-pirazolo[3,4-d]pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
3-(4-amino-1-(1-(3-(3-fluorofenil)-4-okso-4H-kromen-2-il) etil)-1H-pirazolo [3, 4-d]pirimidin-3-il)-N-ciklopropilbenzamid;
2-(1-(4-amino-3-(3-(morpholinil-4-karbonil)fenil)-1H-pirazolo[3,4-d]pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
2-(1-(4-amino-3-(3-(difluorometoksi)fenil)-1H-pirazolo[3,4-d]pirimidin-1-il)etil)-3-(3-fluorofenil)-4H-kromen-4-on;
5-(4-amino-1-(1-(3-(3-fluorofenil)-4-okso-4H-kromen-2-il)etil)-1H-pirazolo [3,4-d] pirimidin-3-il) furan-2-karbaldehid; i
2-[(6-amino-9H-purin-9-il)metil]-6-bromo-3-o-tolil-4H-kromen-4-on;
i njihove farmaceutski prihvatljive soli.
12. Spoj prema bilo kojem od zahtjeva 1-3, naznačen time da spoj je (S)-2-(1-(9H-purin-6-ilamino)etil)-6-fluoro-3-(3-fluorofenil)-4H-kromen-4-on, te njegove farmaceutski prihvatljive soli.
13. Farmaceutski pripravak, naznačen time da sadrži spoj prema bilo kojem od zahtjeva 1-12 i farmaceutski prihvatljiv nosač.
14. Farmaceutski pripravak prema zahtjevu 13, naznačen time da dodatno sadrži jedno ili više dodatnih terapeutskih sredstava koja se biraju od sredstava protiv raka, protuupalnih sredstva, imunosupresivnih sredstava, steroida, ne-steroidnih protuupalnih sredstava, antihistaminika, analgetika, i njihovih smjesa.
15. Spoj prema bilo kojem od zahtjeva 1-12 naznačen time da je za use za uporabu u liječenju bolesti, poremećaja ili stanja koja se biraju iz skupa koji čine upala, glomerulonefritis, uveitis, bolesti ili poremećaji jetre, bolesti bubrega ili poremećaji bubrega, kronična opstruktivna plućna bolest, reumatoidni artritis, upalna bolest crijeva, vaskulitis, dermatitis, osteoartritis, upalna bolest mišića, alergijski rinitis, vaginitis, intersticijski cistitis, skleroderma, osteoporoza, ekcem, alogena ili ksenogena transplantacija, odbacivanje presatka, bolest presatka protiv domaćina, eritemski lupus, plućna fibroza, dermatomiozitis, tiroiditis, miastenija gravis, autoimuna hemolitička anemija, cistična fibroza, kronični recidivirajući hepatitis, primarna bilijarna ciroza, alergijski konjunktivitis, hepatitis, atopijski dermatitis, astma, Sjogrenov sindrom, odbacivanje transplantata organa, multipla skleroza, sindrom Guillain-Barre, autoimuni uveitis, autoimuna hemolitička anemija, perniciozna anemija, autoimuna trombocitopenija, temporalni arteritis, anti-fosfolipidni sindrom, vaskulitisi kao što su Wegenerova granulomatoza, Behcetova bolest, psorijaza, dermatitis herpetiformis, pemfigus vulgaris, vitiligo, Crohnova bolest, kolitis, ulcerozni kolitis, primarna bilijarna ciroza, autoimuni hepatitis, dijabetes tip 1 ili imunološki posredovani dijabetes melitus, Gravesova bolest, Hashimotov tiroiditis, autoimuni ooforitis i orhitis, autoimuni poremećaj nadbubrežne žlijezde, sistemski eritemski lupus, polimiozitis, dermatomiozitis, ankilozirajući spondilitis, odbacivanje transplantata, odbacivanje presatka kože, artritis, bolesti kostiju povezane s povećanom resorpcijom kostiju, ileitis, Barrettov sindrom, sindrom respiratornog poremećaja kod odraslih, kronična opstruktivna bolest dišnih putova; distrofija rožnice, trahom, onhocerkoza, simpatički oftalmitis, endoftalmitis; gingivitis, perjodontitis; tuberkuloza; guba; uremijske komplikacije, nefroza; sklerodermitis, psorijaza, kronične demijelinizirajuće bolesti živčanog sustava, neurodegeneracija povezane s AIDS-om, Alzheimerova bolest, infektivni meningitis, encefalomijelitis, Parkinsonova bolest, Huntingtonova bolest, amiotrofna lateralna skleroza, virusni ili autoimuni encefalitis; autoimuni poremećaji, imunokompleksni vaskulitis, sistemski lupus i lupus erythematosus; sistemski lupus eritematodes (SLE); kardiomiopatija, ishemijska bolest srca, hiperkolesterolemija, ateroskleroza, preeklampsija; kronično zatajenje jetre, traume mozga i leđne moždine, rak, hematopoietički tumori limfoidne linije, leukemija, akutna limfocitna leukemija, akutna limfoblastična leukemija, limfom B stanica, limfom T stanica, Hodgkinov limfom, ne-Hodgkinov limfom, limfom vlasastih stanica i Burkettov limfom; hematopoietički tumori mijeloidne linije, akutna mijelogena leukemija, kronična mijelogena leukemija, mijelodisplastični sindrom, promijelocitna leukemija; karcinom mokraćnog mjehura, karcinom dojke, karcinom debelog crijeva, karcinom bubrega, karcinom jetre, karcinom pluća, rak pluća malih stanica, rak jednjaka, rak žučnog mjehura, rak jajnika, rak gušterače, rak želuca, raka vrata maternice, rak štitnjače, rak prostate, rak kože, karcinom skvamoznih stanica; tumori mezenhimalnog porijekla, fibrosarkom, rabdomiosarkom; tumori središnjeg i perifernog živčanog sustava, astrocitom, neuroblastom, gliom, schwannom; melanom, seminom, teratokarcinom, osteosarkom, pigmentna kseroderma, keratoakantom, folikularnog karcinoma štitnjače, Kapozijev sarkom, kronična limfocitna leukemija, multiplih mijeloma koji uključuju umirujući višestruki mijelom, nesekretorni mijelom, osteosklerotični mijelom, leukemija plazma stanica, solitarni plazmocitom, ekstramedularni plazmocitom, kronična limfocitna leukemija (CLL); ne-Hodgkinov limfom (NHL); akutna mijeloična leukemija (AML); multipli mijelom (MM), limfom malih limfocita (SLL), ili indolentni ne-Hodgkinov limfom (I-NHL).
16. Spoj za uporabu prema zahtjevu 15, naznačen time da se liječenje bolesti provodi istovremeno ili uzastopno s najmanje jednim drugim sredstvom protiv raka, protuupalnim sredstvom, imunosupresivnim sredstvom, steroidnim, ne-steroidnim protuupalnim sredstvom, antihistaminskim sredstvom, analgetikom ili njihovom smjesom.
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