JP2013510133A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2013510133A5 JP2013510133A5 JP2012537454A JP2012537454A JP2013510133A5 JP 2013510133 A5 JP2013510133 A5 JP 2013510133A5 JP 2012537454 A JP2012537454 A JP 2012537454A JP 2012537454 A JP2012537454 A JP 2012537454A JP 2013510133 A5 JP2013510133 A5 JP 2013510133A5
- Authority
- JP
- Japan
- Prior art keywords
- chromen
- amino
- pyrazolo
- pyrimidin
- fluorophenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 125000000217 alkyl group Chemical group 0.000 claims 24
- 229910052739 hydrogen Inorganic materials 0.000 claims 24
- 239000001257 hydrogen Substances 0.000 claims 24
- 150000002431 hydrogen Chemical group 0.000 claims 19
- 229910052736 halogen Inorganic materials 0.000 claims 15
- 150000002367 halogens Chemical group 0.000 claims 15
- 150000001875 compounds Chemical class 0.000 claims 14
- 125000000623 heterocyclic group Chemical group 0.000 claims 12
- 125000000304 alkynyl group Chemical group 0.000 claims 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 10
- 125000001072 heteroaryl group Chemical group 0.000 claims 10
- 125000003342 alkenyl group Chemical group 0.000 claims 9
- 125000003118 aryl group Chemical group 0.000 claims 9
- -1 alkyl hydrogen Chemical compound 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims 7
- 125000005842 heteroatom Chemical group 0.000 claims 7
- 229920006395 saturated elastomer Polymers 0.000 claims 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 6
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 6
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 125000004429 atom Chemical group 0.000 claims 5
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims 4
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 4
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 125000004043 oxo group Chemical group O=* 0.000 claims 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
- 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
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 3
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims 3
- 201000004624 Dermatitis Diseases 0.000 claims 3
- 206010025323 Lymphomas Diseases 0.000 claims 3
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 3
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 3
- 206010052779 Transplant rejections Diseases 0.000 claims 3
- 206010047115 Vasculitis Diseases 0.000 claims 3
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- 150000002357 guanidines Chemical class 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 239000000651 prodrug Substances 0.000 claims 3
- 229940002612 prodrug Drugs 0.000 claims 3
- 201000000596 systemic lupus erythematosus Diseases 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
- 208000036762 Acute promyelocytic leukaemia Diseases 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 208000003950 B-cell lymphoma Diseases 0.000 claims 2
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 2
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims 2
- 208000033222 Biliary cirrhosis primary Diseases 0.000 claims 2
- 201000009030 Carcinoma Diseases 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 2
- 208000035186 Hemolytic Autoimmune Anemia Diseases 0.000 claims 2
- 208000017604 Hodgkin disease Diseases 0.000 claims 2
- 208000021519 Hodgkin lymphoma Diseases 0.000 claims 2
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims 2
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims 2
- 201000003793 Myelodysplastic syndrome Diseases 0.000 claims 2
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims 2
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims 2
- 208000007452 Plasmacytoma Diseases 0.000 claims 2
- 208000012654 Primary biliary cholangitis Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 206010042971 T-cell lymphoma Diseases 0.000 claims 2
- 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 claims 2
- 239000000730 antalgic agent Substances 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
- 201000000448 autoimmune hemolytic anemia Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 210000004027 cell Anatomy 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 201000001981 dermatomyositis Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 201000005787 hematologic cancer Diseases 0.000 claims 2
- 208000019691 hematopoietic and lymphoid cell neoplasm Diseases 0.000 claims 2
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims 2
- 208000006454 hepatitis Diseases 0.000 claims 2
- 231100000283 hepatitis Toxicity 0.000 claims 2
- 239000003018 immunosuppressive agent Substances 0.000 claims 2
- 229940125721 immunosuppressive agent Drugs 0.000 claims 2
- 208000032839 leukemia Diseases 0.000 claims 2
- 206010025135 lupus erythematosus Diseases 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 201000000050 myeloid neoplasm Diseases 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
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 230000003637 steroidlike Effects 0.000 claims 2
- DEMNUISBUXJRNU-UHFFFAOYSA-N 2-(3-fluorophenyl)chromen-4-one Chemical compound FC1=CC=CC(C=2OC3=CC=CC=C3C(=O)C=2)=C1 DEMNUISBUXJRNU-UHFFFAOYSA-N 0.000 claims 1
- LRUBYSGPYGZTCW-UHFFFAOYSA-N 2-(benzimidazol-1-ylmethyl)-3-phenylchromen-4-one Chemical compound C1=NC2=CC=CC=C2N1CC=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 LRUBYSGPYGZTCW-UHFFFAOYSA-N 0.000 claims 1
- FUXPWOAXFPXFQM-UHFFFAOYSA-N 2-(benzimidazol-1-ylmethyl)-6-bromo-3-phenylchromen-4-one Chemical compound O=C1C2=CC(Br)=CC=C2OC(CN2C3=CC=CC=C3N=C2)=C1C1=CC=CC=C1 FUXPWOAXFPXFQM-UHFFFAOYSA-N 0.000 claims 1
- KNLDQJQMLSCBSE-UHFFFAOYSA-N 2-(imidazol-1-ylmethyl)-3-phenylchromen-4-one Chemical compound O1C2=CC=CC=C2C(=O)C(C=2C=CC=CC=2)=C1CN1C=CN=C1 KNLDQJQMLSCBSE-UHFFFAOYSA-N 0.000 claims 1
- GUJVVYUMNWOSAM-UHFFFAOYSA-N 2-(morpholin-4-ylmethyl)-3-phenylchromen-4-one Chemical compound O1C2=CC=CC=C2C(=O)C(C=2C=CC=CC=2)=C1CN1CCOCC1 GUJVVYUMNWOSAM-UHFFFAOYSA-N 0.000 claims 1
- OPKKWFXLIDOABY-UHFFFAOYSA-N 2-(morpholin-4-ylmethyl)-3-phenylchromen-4-one;hydrochloride Chemical compound Cl.O1C2=CC=CC=C2C(=O)C(C=2C=CC=CC=2)=C1CN1CCOCC1 OPKKWFXLIDOABY-UHFFFAOYSA-N 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
- NXTSIMDKVIAFFO-UHFFFAOYSA-N 2-[(4-methylbenzimidazol-1-yl)methyl]-3-phenylchromen-4-one Chemical compound C1=NC=2C(C)=CC=CC=2N1CC=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 NXTSIMDKVIAFFO-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
- MJUTUKAHFNMZCJ-UHFFFAOYSA-N 2-[(6-aminopurin-9-yl)methyl]-3-phenylchromen-4-one Chemical compound C1=NC=2C(N)=NC=NC=2N1CC=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 MJUTUKAHFNMZCJ-UHFFFAOYSA-N 0.000 claims 1
- 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
- XUDDRUSOJKAJIN-UHFFFAOYSA-N 2-[(6-aminopurin-9-yl)methyl]-6-fluoro-3-phenylchromen-4-one Chemical compound C1=NC=2C(N)=NC=NC=2N1CC=1OC2=CC=C(F)C=C2C(=O)C=1C1=CC=CC=C1 XUDDRUSOJKAJIN-UHFFFAOYSA-N 0.000 claims 1
- PIOYUNFOAWXYMM-UHFFFAOYSA-N 2-[(6-aminopurin-9-yl)methyl]-6-methoxy-3-phenylchromen-4-one Chemical compound O=C1C2=CC(OC)=CC=C2OC(CN2C3=NC=NC(N)=C3N=C2)=C1C1=CC=CC=C1 PIOYUNFOAWXYMM-UHFFFAOYSA-N 0.000 claims 1
- NXBXHXMMRGBCBG-UHFFFAOYSA-N 2-[(6-chloropurin-9-yl)methyl]-3-phenylchromen-4-one Chemical compound C1=NC=2C(Cl)=NC=NC=2N1CC=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 NXBXHXMMRGBCBG-UHFFFAOYSA-N 0.000 claims 1
- MBKCAWRSKHQVHJ-UHFFFAOYSA-N 2-[1-(4-amino-3-dibenzofuran-4-ylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=3OC4=CC=CC=C4C=3C=CC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 MBKCAWRSKHQVHJ-UHFFFAOYSA-N 0.000 claims 1
- PGQBFCKXKYQUTK-UHFFFAOYSA-N 2-[1-(4-amino-3-iodopyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(I)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 PGQBFCKXKYQUTK-UHFFFAOYSA-N 0.000 claims 1
- YDHHYLZYPOHZNT-UHFFFAOYSA-N 2-[1-(4-amino-3-iodopyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-phenylchromen-4-one Chemical compound N1=C(I)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 YDHHYLZYPOHZNT-UHFFFAOYSA-N 0.000 claims 1
- VLXZCNOMJWCTLT-UHFFFAOYSA-N 2-[1-(4-amino-3-iodopyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-fluoro-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(I)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=C(F)C=C2C(=O)C=1C1=CC=CC(F)=C1 VLXZCNOMJWCTLT-UHFFFAOYSA-N 0.000 claims 1
- DNGOOLAROADMJS-UHFFFAOYSA-N 2-[1-(4-amino-3-iodopyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-fluoro-3-phenylchromen-4-one Chemical compound N1=C(I)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=C(F)C=C2C(=O)C=1C1=CC=CC=C1 DNGOOLAROADMJS-UHFFFAOYSA-N 0.000 claims 1
- NPBXYLBOCFZDDW-UHFFFAOYSA-N 2-[1-(4-amino-3-iodopyrazolo[3,4-d]pyrimidin-1-yl)propyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(I)C2=C(N)N=CN=C2N1C(CC)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 NPBXYLBOCFZDDW-UHFFFAOYSA-N 0.000 claims 1
- FPFWFNWLFRSIFI-UHFFFAOYSA-N 2-[1-(4-amino-3-pyrimidin-5-ylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=NC=NC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 FPFWFNWLFRSIFI-UHFFFAOYSA-N 0.000 claims 1
- TUNPHVBQBNZERQ-UHFFFAOYSA-N 2-[1-(4-aminopyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-phenylchromen-4-one Chemical compound N1=CC2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 TUNPHVBQBNZERQ-UHFFFAOYSA-N 0.000 claims 1
- JJGUSBYXXDVDIV-UHFFFAOYSA-N 2-[1-(4-aminopyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-bromo-3-phenylchromen-4-one Chemical compound N1=CC2=C(N)N=CN=C2N1C(C)C=1OC2=CC=C(Br)C=C2C(=O)C=1C1=CC=CC=C1 JJGUSBYXXDVDIV-UHFFFAOYSA-N 0.000 claims 1
- XVTASTKBMBXUKM-UHFFFAOYSA-N 2-[1-(4-chloropyrazolo[3,4-b]pyridin-1-yl)ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=CC2=C(Cl)C=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 XVTASTKBMBXUKM-UHFFFAOYSA-N 0.000 claims 1
- TTWOOLOPDWENNU-UHFFFAOYSA-N 2-[1-(4-chloropyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=CC2=C(Cl)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 TTWOOLOPDWENNU-UHFFFAOYSA-N 0.000 claims 1
- QXVNPMGNZYNOFF-UHFFFAOYSA-N 2-[1-(4-chloropyrrolo[2,3-d]pyrimidin-7-yl)ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=CC2=C(Cl)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 QXVNPMGNZYNOFF-UHFFFAOYSA-N 0.000 claims 1
- WENARJGEOUWONT-UHFFFAOYSA-N 2-[1-(4-chloropyrrolo[3,2-d]pyrimidin-5-yl)ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=CC2=NC=NC(Cl)=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 WENARJGEOUWONT-UHFFFAOYSA-N 0.000 claims 1
- WHMLNVHHFADXAM-UHFFFAOYSA-N 2-[1-(6-aminopurin-9-yl)ethyl]-3-(2-fluorophenyl)chromen-4-one Chemical compound C1=NC2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1F WHMLNVHHFADXAM-UHFFFAOYSA-N 0.000 claims 1
- PDXGAHQJUUWJMH-UHFFFAOYSA-N 2-[1-(6-aminopurin-9-yl)ethyl]-3-(2-methylphenyl)chromen-4-one Chemical compound C1=NC2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1C PDXGAHQJUUWJMH-UHFFFAOYSA-N 0.000 claims 1
- WRBMZZRBXMEGAS-UHFFFAOYSA-N 2-[1-(6-aminopurin-9-yl)ethyl]-3-(3,5-difluorophenyl)chromen-4-one Chemical compound C1=NC2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC(F)=CC(F)=C1 WRBMZZRBXMEGAS-UHFFFAOYSA-N 0.000 claims 1
- LQJLKCJAFNRSIS-UHFFFAOYSA-N 2-[1-(6-aminopurin-9-yl)ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=NC2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 LQJLKCJAFNRSIS-UHFFFAOYSA-N 0.000 claims 1
- GUTNLRCCANXFTG-UHFFFAOYSA-N 2-[1-(6-aminopurin-9-yl)ethyl]-3-(4-fluorophenyl)chromen-4-one Chemical compound C1=NC2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=C(F)C=C1 GUTNLRCCANXFTG-UHFFFAOYSA-N 0.000 claims 1
- WCVFGPPHHCNTBO-UHFFFAOYSA-N 2-[1-(6-aminopurin-9-yl)ethyl]-3-phenylchromen-4-one Chemical compound C1=NC2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 WCVFGPPHHCNTBO-UHFFFAOYSA-N 0.000 claims 1
- DDYHHXKNVJDMEG-UHFFFAOYSA-N 2-[1-(6-aminopurin-9-yl)ethyl]-6-bromo-3-(2-fluorophenyl)chromen-4-one Chemical compound C1=NC2=C(N)N=CN=C2N1C(C)C=1OC2=CC=C(Br)C=C2C(=O)C=1C1=CC=CC=C1F DDYHHXKNVJDMEG-UHFFFAOYSA-N 0.000 claims 1
- MQUMBWSSTOIBTG-UHFFFAOYSA-N 2-[1-(6-aminopurin-9-yl)ethyl]-6-bromo-3-phenylchromen-4-one Chemical compound C1=NC2=C(N)N=CN=C2N1C(C)C=1OC2=CC=C(Br)C=C2C(=O)C=1C1=CC=CC=C1 MQUMBWSSTOIBTG-UHFFFAOYSA-N 0.000 claims 1
- SPSNKUIKGMDEJD-UHFFFAOYSA-N 2-[1-(6-aminopurin-9-yl)ethyl]-6-fluoro-3-(2-fluorophenyl)chromen-4-one Chemical compound C1=NC2=C(N)N=CN=C2N1C(C)C=1OC2=CC=C(F)C=C2C(=O)C=1C1=CC=CC=C1F SPSNKUIKGMDEJD-UHFFFAOYSA-N 0.000 claims 1
- PCVWAGVDVPMLSM-UHFFFAOYSA-N 2-[1-(6-aminopurin-9-yl)ethyl]-6-fluoro-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=NC2=C(N)N=CN=C2N1C(C)C=1OC2=CC=C(F)C=C2C(=O)C=1C1=CC=CC(F)=C1 PCVWAGVDVPMLSM-UHFFFAOYSA-N 0.000 claims 1
- PPQTZUGSIRZEIJ-UHFFFAOYSA-N 2-[1-(6-aminopurin-9-yl)ethyl]-6-fluoro-3-phenylchromen-4-one Chemical compound C1=NC2=C(N)N=CN=C2N1C(C)C=1OC2=CC=C(F)C=C2C(=O)C=1C1=CC=CC=C1 PPQTZUGSIRZEIJ-UHFFFAOYSA-N 0.000 claims 1
- RBOOUDKSRYUAHZ-UHFFFAOYSA-N 2-[1-(6-aminopurin-9-yl)propyl]-3-(2-fluorophenyl)chromen-4-one Chemical compound C1=NC2=C(N)N=CN=C2N1C(CC)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1F RBOOUDKSRYUAHZ-UHFFFAOYSA-N 0.000 claims 1
- ZTQWYVKRUMGVGU-UHFFFAOYSA-N 2-[1-(6-aminopurin-9-yl)propyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=NC2=C(N)N=CN=C2N1C(CC)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 ZTQWYVKRUMGVGU-UHFFFAOYSA-N 0.000 claims 1
- UYWOEDSZTCMFHJ-UHFFFAOYSA-N 2-[1-(6-aminopurin-9-yl)propyl]-3-(4-fluorophenyl)chromen-4-one Chemical compound C1=NC2=C(N)N=CN=C2N1C(CC)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=C(F)C=C1 UYWOEDSZTCMFHJ-UHFFFAOYSA-N 0.000 claims 1
- MIAMNONKYCHXOR-UHFFFAOYSA-N 2-[1-(6-aminopurin-9-yl)propyl]-3-phenylchromen-4-one Chemical compound C1=NC2=C(N)N=CN=C2N1C(CC)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 MIAMNONKYCHXOR-UHFFFAOYSA-N 0.000 claims 1
- ANASCSCDTHHCTQ-UHFFFAOYSA-N 2-[1-(6-aminopurin-9-yl)propyl]-6-fluoro-3-phenylchromen-4-one Chemical compound C1=NC2=C(N)N=CN=C2N1C(CC)C=1OC2=CC=C(F)C=C2C(=O)C=1C1=CC=CC=C1 ANASCSCDTHHCTQ-UHFFFAOYSA-N 0.000 claims 1
- WTOFSHVCFTVROT-UHFFFAOYSA-N 2-[1-[3-(4-acetylphenyl)-4-aminopyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=CC(=CC=2)C(C)=O)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 WTOFSHVCFTVROT-UHFFFAOYSA-N 0.000 claims 1
- KMGFVPJVXGLYKF-UHFFFAOYSA-N 2-[1-[4-amino-3-(1,3-dimethylindazol-6-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=C3N(C)N=C(C)C3=CC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 KMGFVPJVXGLYKF-UHFFFAOYSA-N 0.000 claims 1
- NHWATMCZOFXVFA-UHFFFAOYSA-N 2-[1-[4-amino-3-(1-benzothiophen-2-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2SC3=CC=CC=C3C=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 NHWATMCZOFXVFA-UHFFFAOYSA-N 0.000 claims 1
- QMSGHMSDKYEFBC-UHFFFAOYSA-N 2-[1-[4-amino-3-(1-benzothiophen-3-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C3=CC=CC=C3SC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 QMSGHMSDKYEFBC-UHFFFAOYSA-N 0.000 claims 1
- OXNJJFOPTHHSKM-UHFFFAOYSA-N 2-[1-[4-amino-3-(1-benzylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C2=CN(CC=3C=CC=CC=3)N=C2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 OXNJJFOPTHHSKM-UHFFFAOYSA-N 0.000 claims 1
- RYHWOVPFDPFFFC-UHFFFAOYSA-N 2-[1-[4-amino-3-(1-methylpyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C2=CN(C)N=C2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 RYHWOVPFDPFFFC-UHFFFAOYSA-N 0.000 claims 1
- YADMBQDAPMBJPL-UHFFFAOYSA-N 2-[1-[4-amino-3-(1H-pyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C2=CNN=C2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 YADMBQDAPMBJPL-UHFFFAOYSA-N 0.000 claims 1
- OBYQJRVAYOCOHS-UHFFFAOYSA-N 2-[1-[4-amino-3-(1H-pyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-phenylchromen-4-one Chemical compound N1=C(C2=CNN=C2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 OBYQJRVAYOCOHS-UHFFFAOYSA-N 0.000 claims 1
- CFDJNGSAXMSCAB-UHFFFAOYSA-N 2-[1-[4-amino-3-(1h-indazol-4-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 CFDJNGSAXMSCAB-UHFFFAOYSA-N 0.000 claims 1
- SULMZJPPHJCQAG-UHFFFAOYSA-N 2-[1-[4-amino-3-(1h-indazol-6-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=C3NN=CC3=CC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 SULMZJPPHJCQAG-UHFFFAOYSA-N 0.000 claims 1
- IFBIAELGPWWSIN-UHFFFAOYSA-N 2-[1-[4-amino-3-(1h-indazol-6-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-phenylchromen-4-one Chemical compound N1=C(C=2C=C3NN=CC3=CC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 IFBIAELGPWWSIN-UHFFFAOYSA-N 0.000 claims 1
- JLFPEPJISNHSFG-UHFFFAOYSA-N 2-[1-[4-amino-3-(1h-indol-5-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=C3C=CNC3=CC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 JLFPEPJISNHSFG-UHFFFAOYSA-N 0.000 claims 1
- JSQUPSMNEOFWJL-UHFFFAOYSA-N 2-[1-[4-amino-3-(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=CC3=CC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 JSQUPSMNEOFWJL-UHFFFAOYSA-N 0.000 claims 1
- AOXMZECLAXUJAJ-UHFFFAOYSA-N 2-[1-[4-amino-3-(2,3-dihydro-1-benzofuran-5-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=C3CCOC3=CC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 AOXMZECLAXUJAJ-UHFFFAOYSA-N 0.000 claims 1
- SHKZPJLCQLDFGC-UHFFFAOYSA-N 2-[1-[4-amino-3-(2,3-dimethylindazol-6-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C2=CC3=NN(C)C(C)=C3C=C2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 SHKZPJLCQLDFGC-UHFFFAOYSA-N 0.000 claims 1
- PNFXXEMIFUUZDT-UHFFFAOYSA-N 2-[1-[4-amino-3-(2,4-dimethoxypyrimidin-5-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound COC1=NC(OC)=NC=C1C(C1=C(N)N=CN=C11)=NN1C(C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC=CC=C2O1 PNFXXEMIFUUZDT-UHFFFAOYSA-N 0.000 claims 1
- VINNLUFXBGOMKO-UHFFFAOYSA-N 2-[1-[4-amino-3-(2-aminopyrimidin-5-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=NC(N)=NC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 VINNLUFXBGOMKO-UHFFFAOYSA-N 0.000 claims 1
- WDZUIGIYDAIDGH-UHFFFAOYSA-N 2-[1-[4-amino-3-(2-chloro-5-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C(=CC=C(O)C=2)Cl)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 WDZUIGIYDAIDGH-UHFFFAOYSA-N 0.000 claims 1
- KZTWDJBRPHJDFS-UHFFFAOYSA-N 2-[1-[4-amino-3-(2-chloro-5-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound COC1=CC=C(Cl)C(C=2C3=C(N)N=CN=C3N(C(C)C3=C(C(=O)C4=CC=CC=C4O3)C=3C=C(F)C=CC=3)N=2)=C1 KZTWDJBRPHJDFS-UHFFFAOYSA-N 0.000 claims 1
- SBDFBGGLLBNGLI-UHFFFAOYSA-N 2-[1-[4-amino-3-(2-fluoro-5-propan-2-yloxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound CC(C)OC1=CC=C(F)C(C=2C3=C(N)N=CN=C3N(C(C)C3=C(C(=O)C4=CC=CC=C4O3)C=3C=C(F)C=CC=3)N=2)=C1 SBDFBGGLLBNGLI-UHFFFAOYSA-N 0.000 claims 1
- CGMHDGQXROSQBH-UHFFFAOYSA-N 2-[1-[4-amino-3-(2-methoxypyrimidin-5-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=NC(OC)=NC=C1C(C1=C(N)N=CN=C11)=NN1C(C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC=CC=C2O1 CGMHDGQXROSQBH-UHFFFAOYSA-N 0.000 claims 1
- MFJQHXYUYKAYAE-UHFFFAOYSA-N 2-[1-[4-amino-3-(2-methyl-3h-benzimidazol-5-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=C3N=C(C)NC3=CC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 MFJQHXYUYKAYAE-UHFFFAOYSA-N 0.000 claims 1
- DOBFXWQOANAAJJ-UHFFFAOYSA-N 2-[1-[4-amino-3-(2-methylpyridin-4-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=C(C)N=CC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 DOBFXWQOANAAJJ-UHFFFAOYSA-N 0.000 claims 1
- DUZVMXWASHURJC-UHFFFAOYSA-N 2-[1-[4-amino-3-(3,4-dihydro-2h-1,5-benzodioxepin-7-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=C3OCCCOC3=CC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 DUZVMXWASHURJC-UHFFFAOYSA-N 0.000 claims 1
- NDOQLBGVBSTAET-UHFFFAOYSA-N 2-[1-[4-amino-3-(3,4-dihydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=C(O)C(O)=CC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 NDOQLBGVBSTAET-UHFFFAOYSA-N 0.000 claims 1
- CIBVELZRMDRRJB-UHFFFAOYSA-N 2-[1-[4-amino-3-(3,4-dimethoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=C(OC)C(OC)=CC=C1C(C1=C(N)N=CN=C11)=NN1C(C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC=CC=C2O1 CIBVELZRMDRRJB-UHFFFAOYSA-N 0.000 claims 1
- IJDOFEDUQRJLKN-UHFFFAOYSA-N 2-[1-[4-amino-3-(3,5-difluoro-4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=C(F)C(O)=C(F)C=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 IJDOFEDUQRJLKN-UHFFFAOYSA-N 0.000 claims 1
- ORQVODPMLSLGJE-UHFFFAOYSA-N 2-[1-[4-amino-3-(3,5-difluoro-4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=C(F)C(OC)=C(F)C=C1C(C1=C(N)N=CN=C11)=NN1C(C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC=CC=C2O1 ORQVODPMLSLGJE-UHFFFAOYSA-N 0.000 claims 1
- XIOJHCARRQDZII-UHFFFAOYSA-N 2-[1-[4-amino-3-(3,5-dimethoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound COC1=CC(OC)=CC(C=2C3=C(N)N=CN=C3N(C(C)C3=C(C(=O)C4=CC=CC=C4O3)C=3C=C(F)C=CC=3)N=2)=C1 XIOJHCARRQDZII-UHFFFAOYSA-N 0.000 claims 1
- KFHJCGXPUWRDGH-UHFFFAOYSA-N 2-[1-[4-amino-3-(3,5-dimethyl-1,2-oxazol-4-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C2=C(ON=C2C)C)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 KFHJCGXPUWRDGH-UHFFFAOYSA-N 0.000 claims 1
- UHQKKSUJFKTELT-UHFFFAOYSA-N 2-[1-[4-amino-3-(3,5-dimethyl-1H-pyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C2=C(NN=C2C)C)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 UHQKKSUJFKTELT-UHFFFAOYSA-N 0.000 claims 1
- AMHTZVQYUKTAQM-UHFFFAOYSA-N 2-[1-[4-amino-3-(3-chloro-4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=C(Cl)C(OC)=CC=C1C(C1=C(N)N=CN=C11)=NN1C(C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC=CC=C2O1 AMHTZVQYUKTAQM-UHFFFAOYSA-N 0.000 claims 1
- GPDSRNILOMHHMY-UHFFFAOYSA-N 2-[1-[4-amino-3-(3-chloro-4-phenylmethoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=C(Cl)C(OCC=3C=CC=CC=3)=CC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 GPDSRNILOMHHMY-UHFFFAOYSA-N 0.000 claims 1
- BDYPLKRRXQXDOB-UHFFFAOYSA-N 2-[1-[4-amino-3-(3-chloro-4-propan-2-yloxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C(C1=C(N)N=CN=C11)=NN1C(C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC=CC=C2O1 BDYPLKRRXQXDOB-UHFFFAOYSA-N 0.000 claims 1
- VPZUXWMJTOPCOQ-UHFFFAOYSA-N 2-[1-[4-amino-3-(3-chloro-5-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=C(Cl)C=C(O)C=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 VPZUXWMJTOPCOQ-UHFFFAOYSA-N 0.000 claims 1
- JPIZBWXMSODEOF-UHFFFAOYSA-N 2-[1-[4-amino-3-(3-chloro-5-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound COC1=CC(Cl)=CC(C=2C3=C(N)N=CN=C3N(C(C)C3=C(C(=O)C4=CC=CC=C4O3)C=3C=C(F)C=CC=3)N=2)=C1 JPIZBWXMSODEOF-UHFFFAOYSA-N 0.000 claims 1
- XPMKAPWWVJDMTO-UHFFFAOYSA-N 2-[1-[4-amino-3-(3-ethoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound CCOC1=CC=CC(C=2C3=C(N)N=CN=C3N(C(C)C3=C(C(=O)C4=CC=CC=C4O3)C=3C=C(F)C=CC=3)N=2)=C1 XPMKAPWWVJDMTO-UHFFFAOYSA-N 0.000 claims 1
- NVXZLKSZWIXXBN-UHFFFAOYSA-N 2-[1-[4-amino-3-(3-ethyl-2h-indazol-6-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound C=1C=C2C(CC)=NNC2=CC=1C(C1=C(N)N=CN=C11)=NN1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 NVXZLKSZWIXXBN-UHFFFAOYSA-N 0.000 claims 1
- CKIXKPSRAAMSMA-UHFFFAOYSA-N 2-[1-[4-amino-3-(3-fluoro-4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=C(F)C(O)=CC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 CKIXKPSRAAMSMA-UHFFFAOYSA-N 0.000 claims 1
- FHEVWNCATJTNQI-UHFFFAOYSA-N 2-[1-[4-amino-3-(3-fluoro-4-propan-2-yloxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=C(F)C(OC(C)C)=CC=C1C(C1=C(N)N=CN=C11)=NN1C(C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC=CC=C2O1 FHEVWNCATJTNQI-UHFFFAOYSA-N 0.000 claims 1
- SBQLJRFAKSJIIV-UHFFFAOYSA-N 2-[1-[4-amino-3-(3-fluoro-5-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=C(F)C=C(O)C=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 SBQLJRFAKSJIIV-UHFFFAOYSA-N 0.000 claims 1
- AMSPHYVCFMBOQP-UHFFFAOYSA-N 2-[1-[4-amino-3-(3-fluoro-5-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound COC1=CC(F)=CC(C=2C3=C(N)N=CN=C3N(C(C)C3=C(C(=O)C4=CC=CC=C4O3)C=3C=C(F)C=CC=3)N=2)=C1 AMSPHYVCFMBOQP-UHFFFAOYSA-N 0.000 claims 1
- KKGZLCIFBMDQFL-UHFFFAOYSA-N 2-[1-[4-amino-3-(3-hydroxy-3-methylbut-1-ynyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-phenylchromen-4-one Chemical compound N1=C(C#CC(C)(C)O)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 KKGZLCIFBMDQFL-UHFFFAOYSA-N 0.000 claims 1
- AYYNAPOYRUSCIA-UHFFFAOYSA-N 2-[1-[4-amino-3-(3-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=C(O)C=CC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 AYYNAPOYRUSCIA-UHFFFAOYSA-N 0.000 claims 1
- OLHGHOXDOPRFKM-UHFFFAOYSA-N 2-[1-[4-amino-3-(3-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-6-fluoro-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=C(O)C=CC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=C(F)C=C2C(=O)C=1C1=CC=CC(F)=C1 OLHGHOXDOPRFKM-UHFFFAOYSA-N 0.000 claims 1
- UJSQOCOZCRWDCK-UHFFFAOYSA-N 2-[1-[4-amino-3-(3-hydroxyprop-1-ynyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C#CCO)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 UJSQOCOZCRWDCK-UHFFFAOYSA-N 0.000 claims 1
- FBEWCILIJXQXCM-UHFFFAOYSA-N 2-[1-[4-amino-3-(3-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound COC1=CC=CC(C=2C3=C(N)N=CN=C3N(C(C)C3=C(C(=O)C4=CC=CC=C4O3)C=3C=C(F)C=CC=3)N=2)=C1 FBEWCILIJXQXCM-UHFFFAOYSA-N 0.000 claims 1
- BRZJATUQKNKTMQ-UHFFFAOYSA-N 2-[1-[4-amino-3-(3-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-phenylchromen-4-one Chemical compound COC1=CC=CC(C=2C3=C(N)N=CN=C3N(C(C)C3=C(C(=O)C4=CC=CC=C4O3)C=3C=CC=CC=3)N=2)=C1 BRZJATUQKNKTMQ-UHFFFAOYSA-N 0.000 claims 1
- ODFOTLWTOFAEPU-UHFFFAOYSA-N 2-[1-[4-amino-3-(3-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-6-fluoro-3-(3-fluorophenyl)chromen-4-one Chemical compound COC1=CC=CC(C=2C3=C(N)N=CN=C3N(C(C)C3=C(C(=O)C4=CC(F)=CC=C4O3)C=3C=C(F)C=CC=3)N=2)=C1 ODFOTLWTOFAEPU-UHFFFAOYSA-N 0.000 claims 1
- JALHYRCAJISPSK-UHFFFAOYSA-N 2-[1-[4-amino-3-(3-methyl-1h-indol-5-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=C3C(C)=CNC3=CC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 JALHYRCAJISPSK-UHFFFAOYSA-N 0.000 claims 1
- IZILECHNHHYDBW-UHFFFAOYSA-N 2-[1-[4-amino-3-(3-methyl-2h-indazol-5-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=C3C(C)=NNC3=CC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 IZILECHNHHYDBW-UHFFFAOYSA-N 0.000 claims 1
- GVJSTFKNCWGFNQ-UHFFFAOYSA-N 2-[1-[4-amino-3-(3-methyl-2h-indazol-6-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-phenylchromen-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=C1 GVJSTFKNCWGFNQ-UHFFFAOYSA-N 0.000 claims 1
- NTIKTXVBWJDGQC-UHFFFAOYSA-N 2-[1-[4-amino-3-(3-methyl-2h-indazol-6-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-6-fluoro-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=C(F)C=C2C(=O)C=1C1=CC=CC(F)=C1 NTIKTXVBWJDGQC-UHFFFAOYSA-N 0.000 claims 1
- ZKSDGDXGKFQIHY-UHFFFAOYSA-N 2-[1-[4-amino-3-(3-methyl-2h-indazol-6-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-6-fluoro-3-phenylchromen-4-one Chemical compound N1=C(C=2C=C3NN=C(C)C3=CC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=C(F)C=C2C(=O)C=1C1=CC=CC=C1 ZKSDGDXGKFQIHY-UHFFFAOYSA-N 0.000 claims 1
- KQWICTOYVIZZNQ-UHFFFAOYSA-N 2-[1-[4-amino-3-(3-methyl-2h-indazol-6-yl)pyrazolo[3,4-d]pyrimidin-1-yl]propyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=C3NN=C(C)C3=CC=2)C2=C(N)N=CN=C2N1C(CC)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 KQWICTOYVIZZNQ-UHFFFAOYSA-N 0.000 claims 1
- IVPSADBFFXZFDI-UHFFFAOYSA-N 2-[1-[4-amino-3-(3-propan-2-yloxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound CC(C)OC1=CC=CC(C=2C3=C(N)N=CN=C3N(C(C)C3=C(C(=O)C4=CC=CC=C4O3)C=3C=C(F)C=CC=3)N=2)=C1 IVPSADBFFXZFDI-UHFFFAOYSA-N 0.000 claims 1
- QBLDOWKUGHZFDJ-UHFFFAOYSA-N 2-[1-[4-amino-3-(3-propoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound CCCOC1=CC=CC(C=2C3=C(N)N=CN=C3N(C(C)C3=C(C(=O)C4=CC=CC=C4O3)C=3C=C(F)C=CC=3)N=2)=C1 QBLDOWKUGHZFDJ-UHFFFAOYSA-N 0.000 claims 1
- CJZZZMGISNRYTE-UHFFFAOYSA-N 2-[1-[4-amino-3-(4-aminophenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=CC(N)=CC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 CJZZZMGISNRYTE-UHFFFAOYSA-N 0.000 claims 1
- DINYZBFXTRKPEP-UHFFFAOYSA-N 2-[1-[4-amino-3-(4-chloro-3-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=C(O)C(Cl)=CC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 DINYZBFXTRKPEP-UHFFFAOYSA-N 0.000 claims 1
- ZJYWZRAWNUJEKZ-UHFFFAOYSA-N 2-[1-[4-amino-3-(4-chloro-3-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=C(Cl)C(OC)=CC(C=2C3=C(N)N=CN=C3N(C(C)C3=C(C(=O)C4=CC=CC=C4O3)C=3C=C(F)C=CC=3)N=2)=C1 ZJYWZRAWNUJEKZ-UHFFFAOYSA-N 0.000 claims 1
- AZTFVMCIZJWZGQ-UHFFFAOYSA-N 2-[1-[4-amino-3-(4-ethoxy-3-fluorophenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=C(F)C(OCC)=CC=C1C(C1=C(N)N=CN=C11)=NN1C(C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC=CC=C2O1 AZTFVMCIZJWZGQ-UHFFFAOYSA-N 0.000 claims 1
- XSHPUOZMLPXKDK-UHFFFAOYSA-N 2-[1-[4-amino-3-(4-ethoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=CC(OCC)=CC=C1C(C1=C(N)N=CN=C11)=NN1C(C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC=CC=C2O1 XSHPUOZMLPXKDK-UHFFFAOYSA-N 0.000 claims 1
- XKXTVKJCTVHECM-UHFFFAOYSA-N 2-[1-[4-amino-3-(4-fluoro-2-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C(=CC(F)=CC=2)O)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 XKXTVKJCTVHECM-UHFFFAOYSA-N 0.000 claims 1
- MMCLUNWEZMQBKS-UHFFFAOYSA-N 2-[1-[4-amino-3-(4-fluoro-2-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound COC1=CC(F)=CC=C1C(C1=C(N)N=CN=C11)=NN1C(C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC=CC=C2O1 MMCLUNWEZMQBKS-UHFFFAOYSA-N 0.000 claims 1
- ZORLBRQMMPZVDI-UHFFFAOYSA-N 2-[1-[4-amino-3-(4-fluoro-3-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=C(O)C(F)=CC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 ZORLBRQMMPZVDI-UHFFFAOYSA-N 0.000 claims 1
- CQVUSIIYIFYUPQ-UHFFFAOYSA-N 2-[1-[4-amino-3-(4-fluoro-3-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=C(F)C(OC)=CC(C=2C3=C(N)N=CN=C3N(C(C)C3=C(C(=O)C4=CC=CC=C4O3)C=3C=C(F)C=CC=3)N=2)=C1 CQVUSIIYIFYUPQ-UHFFFAOYSA-N 0.000 claims 1
- KAWDGYFZZWQAPX-UHFFFAOYSA-N 2-[1-[4-amino-3-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=CC(O)=CC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 KAWDGYFZZWQAPX-UHFFFAOYSA-N 0.000 claims 1
- CFDHGHZQANZOIQ-UHFFFAOYSA-N 2-[1-[4-amino-3-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=CC(OC)=CC=C1C(C1=C(N)N=CN=C11)=NN1C(C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC=CC=C2O1 CFDHGHZQANZOIQ-UHFFFAOYSA-N 0.000 claims 1
- ZKCRTOZPGSGKQG-UHFFFAOYSA-N 2-[1-[4-amino-3-(4-methylsulfonylphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=CC(=CC=2)S(C)(=O)=O)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 ZKCRTOZPGSGKQG-UHFFFAOYSA-N 0.000 claims 1
- XWPUHQXTFNEAQO-UHFFFAOYSA-N 2-[1-[4-amino-3-(4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=CC(OC=3C=CC=CC=3)=CC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 XWPUHQXTFNEAQO-UHFFFAOYSA-N 0.000 claims 1
- ASDWTQQVKUSQQS-UHFFFAOYSA-N 2-[1-[4-amino-3-(4-propan-2-yloxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=CC(OC(C)C)=CC=C1C(C1=C(N)N=CN=C11)=NN1C(C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC=CC=C2O1 ASDWTQQVKUSQQS-UHFFFAOYSA-N 0.000 claims 1
- QJJPVMRHEVOZOW-UHFFFAOYSA-N 2-[1-[4-amino-3-(5-chlorothiophen-2-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2SC(Cl)=CC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 QJJPVMRHEVOZOW-UHFFFAOYSA-N 0.000 claims 1
- RQVZPWAJWHSYSD-UHFFFAOYSA-N 2-[1-[4-amino-3-(6-ethoxynaphthalen-2-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=CC2=CC(OCC)=CC=C2C=C1C(C1=C(N)N=CN=C11)=NN1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 RQVZPWAJWHSYSD-UHFFFAOYSA-N 0.000 claims 1
- HWBAQRDRGWKPRF-UHFFFAOYSA-N 2-[1-[4-amino-3-(6-hydroxynaphthalen-2-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=C3C=CC(O)=CC3=CC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 HWBAQRDRGWKPRF-UHFFFAOYSA-N 0.000 claims 1
- LOLSEUUHDYWBFI-UHFFFAOYSA-N 2-[1-[4-amino-3-(6-methoxynaphthalen-2-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=CC2=CC(OC)=CC=C2C=C1C(C1=C(N)N=CN=C11)=NN1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 LOLSEUUHDYWBFI-UHFFFAOYSA-N 0.000 claims 1
- QMUUANYDBXDVNV-UHFFFAOYSA-N 2-[1-[4-amino-3-(6-morpholin-4-ylpyridin-3-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=NC(=CC=2)N2CCOCC2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 QMUUANYDBXDVNV-UHFFFAOYSA-N 0.000 claims 1
- SHAQDEKUZAXZNE-UHFFFAOYSA-N 2-[1-[4-amino-3-(furan-2-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2OC=CC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 SHAQDEKUZAXZNE-UHFFFAOYSA-N 0.000 claims 1
- FNZFMFNRQUQGHZ-UHFFFAOYSA-N 2-[1-[4-amino-3-[2-(hydroxymethyl)phenyl]pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C(=CC=CC=2)CO)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 FNZFMFNRQUQGHZ-UHFFFAOYSA-N 0.000 claims 1
- WAXGCFWXLLFLDX-UHFFFAOYSA-N 2-[1-[4-amino-3-[3-(difluoromethoxy)phenyl]pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=C(OC(F)F)C=CC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 WAXGCFWXLLFLDX-UHFFFAOYSA-N 0.000 claims 1
- GMWDLMHEXDHTGW-UHFFFAOYSA-N 2-[1-[4-amino-3-[3-(methoxymethyl)phenyl]pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound COCC1=CC=CC(C=2C3=C(N)N=CN=C3N(C(C)C3=C(C(=O)C4=CC=CC=C4O3)C=3C=C(F)C=CC=3)N=2)=C1 GMWDLMHEXDHTGW-UHFFFAOYSA-N 0.000 claims 1
- DFHBINSLXFDCQF-UHFFFAOYSA-N 2-[1-[4-amino-3-[3-(trifluoromethoxy)phenyl]pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=C(OC(F)(F)F)C=CC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 DFHBINSLXFDCQF-UHFFFAOYSA-N 0.000 claims 1
- HQOQLYBWKRGJSW-UHFFFAOYSA-N 2-[1-[4-amino-3-[4-(dimethylamino)phenyl]pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=CC(=CC=2)N(C)C)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 HQOQLYBWKRGJSW-UHFFFAOYSA-N 0.000 claims 1
- KFOLFBGBWBBRDF-UHFFFAOYSA-N 2-[1-[4-amino-3-[4-(trifluoromethoxy)phenyl]pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=CC(OC(F)(F)F)=CC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 KFOLFBGBWBBRDF-UHFFFAOYSA-N 0.000 claims 1
- YDDMFSLDLBFJPA-UHFFFAOYSA-N 2-[1-[4-amino-3-[5-(aminomethyl)thiophen-2-yl]pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2SC(CN)=CC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 YDDMFSLDLBFJPA-UHFFFAOYSA-N 0.000 claims 1
- HIOYVPPFYAZOAB-UHFFFAOYSA-N 2-[1-[4-amino-3-[5-(hydroxymethyl)thiophen-3-yl]pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=C(CO)SC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 HIOYVPPFYAZOAB-UHFFFAOYSA-N 0.000 claims 1
- IGGSZDBVXFNIPF-UHFFFAOYSA-N 2-[[4-amino-3-(1H-pyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-phenylchromen-4-one Chemical compound N1=C(C2=CNN=C2)C=2C(N)=NC=NC=2N1CC=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 IGGSZDBVXFNIPF-UHFFFAOYSA-N 0.000 claims 1
- QZLFDCQGOYUAPF-UHFFFAOYSA-N 2-[[4-amino-3-(1H-pyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-6-fluoro-3-phenylchromen-4-one Chemical compound N1=C(C2=CNN=C2)C=2C(N)=NC=NC=2N1CC=1OC2=CC=C(F)C=C2C(=O)C=1C1=CC=CC=C1 QZLFDCQGOYUAPF-UHFFFAOYSA-N 0.000 claims 1
- BNMXDEDATYZUTI-UHFFFAOYSA-N 2-[[4-amino-3-(1h-indazol-4-yl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-phenylchromen-4-one Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)C=2C(N)=NC=NC=2N1CC=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 BNMXDEDATYZUTI-UHFFFAOYSA-N 0.000 claims 1
- DSPMEDKWOGLFMH-UHFFFAOYSA-N 2-[[4-amino-3-(1h-indazol-6-yl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-phenylchromen-4-one Chemical compound N1=C(C=2C=C3NN=CC3=CC=2)C=2C(N)=NC=NC=2N1CC=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 DSPMEDKWOGLFMH-UHFFFAOYSA-N 0.000 claims 1
- YWAJTRDSPBIHBT-UHFFFAOYSA-N 2-[[4-amino-3-(3,5-difluoro-4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-6-fluoro-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=C(F)C(O)=C(F)C=2)C=2C(N)=NC=NC=2N1CC=1OC2=CC=C(F)C=C2C(=O)C=1C1=CC=CC(F)=C1 YWAJTRDSPBIHBT-UHFFFAOYSA-N 0.000 claims 1
- UBAIFMORHOZTOK-UHFFFAOYSA-N 2-[[4-amino-3-(3,5-difluoro-4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-6-fluoro-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=C(F)C(OC)=C(F)C=C1C(C1=C(N)N=CN=C11)=NN1CC1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC(F)=CC=C2O1 UBAIFMORHOZTOK-UHFFFAOYSA-N 0.000 claims 1
- HFCNWCHEKAHFSJ-UHFFFAOYSA-N 2-[[4-amino-3-(3-aminophenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-phenylchromen-4-one Chemical compound NC1=CC=CC(C=2C3=C(N)N=CN=C3N(CC3=C(C(=O)C4=CC=CC=C4O3)C=3C=CC=CC=3)N=2)=C1 HFCNWCHEKAHFSJ-UHFFFAOYSA-N 0.000 claims 1
- VGWQJRGDBYWHPC-UHFFFAOYSA-N 2-[[4-amino-3-(3-fluoro-5-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=C(F)C=C(O)C=2)C=2C(N)=NC=NC=2N1CC=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 VGWQJRGDBYWHPC-UHFFFAOYSA-N 0.000 claims 1
- PTZNGRKSMAWYFJ-UHFFFAOYSA-N 2-[[4-amino-3-(3-fluoro-5-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-phenylchromen-4-one Chemical compound N1=C(C=2C=C(F)C=C(O)C=2)C=2C(N)=NC=NC=2N1CC=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 PTZNGRKSMAWYFJ-UHFFFAOYSA-N 0.000 claims 1
- CTJKGPPVGRIBTL-UHFFFAOYSA-N 2-[[4-amino-3-(3-fluoro-5-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-6-fluoro-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=C(F)C=C(O)C=2)C=2C(N)=NC=NC=2N1CC=1OC2=CC=C(F)C=C2C(=O)C=1C1=CC=CC(F)=C1 CTJKGPPVGRIBTL-UHFFFAOYSA-N 0.000 claims 1
- DEFYFJDUMZNGRZ-UHFFFAOYSA-N 2-[[4-amino-3-(3-fluoro-5-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound COC1=CC(F)=CC(C=2C3=C(N)N=CN=C3N(CC3=C(C(=O)C4=CC=CC=C4O3)C=3C=C(F)C=CC=3)N=2)=C1 DEFYFJDUMZNGRZ-UHFFFAOYSA-N 0.000 claims 1
- WLYNJYWCTVTHJA-UHFFFAOYSA-N 2-[[4-amino-3-(3-fluoro-5-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-phenylchromen-4-one Chemical compound COC1=CC(F)=CC(C=2C3=C(N)N=CN=C3N(CC3=C(C(=O)C4=CC=CC=C4O3)C=3C=CC=CC=3)N=2)=C1 WLYNJYWCTVTHJA-UHFFFAOYSA-N 0.000 claims 1
- HQKSWGCMRYNXBD-UHFFFAOYSA-N 2-[[4-amino-3-(3-fluoro-5-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-6-fluoro-3-(3-fluorophenyl)chromen-4-one Chemical compound COC1=CC(F)=CC(C=2C3=C(N)N=CN=C3N(CC3=C(C(=O)C4=CC(F)=CC=C4O3)C=3C=C(F)C=CC=3)N=2)=C1 HQKSWGCMRYNXBD-UHFFFAOYSA-N 0.000 claims 1
- BMPPSJSGHPXWEM-UHFFFAOYSA-N 2-[[4-amino-3-(3-fluorophenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-phenylchromen-4-one Chemical compound N1=C(C=2C=C(F)C=CC=2)C=2C(N)=NC=NC=2N1CC=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 BMPPSJSGHPXWEM-UHFFFAOYSA-N 0.000 claims 1
- AXTQRIYBBVIIOA-UHFFFAOYSA-N 2-[[4-amino-3-(3-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound N1=C(C=2C=C(O)C=CC=2)C=2C(N)=NC=NC=2N1CC=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 AXTQRIYBBVIIOA-UHFFFAOYSA-N 0.000 claims 1
- XOIXTQRKYMNJID-UHFFFAOYSA-N 2-[[4-amino-3-(3-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-phenylchromen-4-one Chemical compound N1=C(C=2C=C(O)C=CC=2)C=2C(N)=NC=NC=2N1CC=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 XOIXTQRKYMNJID-UHFFFAOYSA-N 0.000 claims 1
- MNBIGEFEXDPCBE-UHFFFAOYSA-N 2-[[4-amino-3-(3-hydroxyprop-1-ynyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-phenylchromen-4-one Chemical compound N1=C(C#CCO)C=2C(N)=NC=NC=2N1CC=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 MNBIGEFEXDPCBE-UHFFFAOYSA-N 0.000 claims 1
- FJELXXKKBCPXLD-UHFFFAOYSA-N 2-[[4-amino-3-(3-hydroxypropyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-phenylchromen-4-one Chemical compound N1=C(CCCO)C=2C(N)=NC=NC=2N1CC=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 FJELXXKKBCPXLD-UHFFFAOYSA-N 0.000 claims 1
- SUORMPWTFOFTCW-UHFFFAOYSA-N 2-[[4-amino-3-(3-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound COC1=CC=CC(C=2C3=C(N)N=CN=C3N(CC3=C(C(=O)C4=CC=CC=C4O3)C=3C=C(F)C=CC=3)N=2)=C1 SUORMPWTFOFTCW-UHFFFAOYSA-N 0.000 claims 1
- OFAWXEAIXKHVLZ-UHFFFAOYSA-N 2-[[4-amino-3-(3-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-phenylchromen-4-one Chemical compound COC1=CC=CC(C=2C3=C(N)N=CN=C3N(CC3=C(C(=O)C4=CC=CC=C4O3)C=3C=CC=CC=3)N=2)=C1 OFAWXEAIXKHVLZ-UHFFFAOYSA-N 0.000 claims 1
- ROTZVQQRRWIHKH-UHFFFAOYSA-N 2-[[4-amino-3-(3-methyl-2h-indazol-6-yl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-(3-fluorophenyl)chromen-4-one Chemical compound C=1C=C2C(C)=NNC2=CC=1C(C1=C(N)N=CN=C11)=NN1CC=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 ROTZVQQRRWIHKH-UHFFFAOYSA-N 0.000 claims 1
- OIIZKFYUTZREAR-UHFFFAOYSA-N 2-[[4-amino-3-(3-methyl-2h-indazol-6-yl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-phenylchromen-4-one Chemical compound C=1C=C2C(C)=NNC2=CC=1C(C1=C(N)N=CN=C11)=NN1CC=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 OIIZKFYUTZREAR-UHFFFAOYSA-N 0.000 claims 1
- CTWOZELQQJJRFF-UHFFFAOYSA-N 2-[[4-amino-3-(3-methyl-2h-indazol-6-yl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-6-fluoro-3-phenylchromen-4-one Chemical compound C=1C=C2C(C)=NNC2=CC=1C(C1=C(N)N=CN=C11)=NN1CC=1OC2=CC=C(F)C=C2C(=O)C=1C1=CC=CC=C1 CTWOZELQQJJRFF-UHFFFAOYSA-N 0.000 claims 1
- RBPYUIYVYGSPKB-UHFFFAOYSA-N 2-[[4-amino-3-[3-(hydroxymethyl)phenyl]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-phenylchromen-4-one Chemical compound N1=C(C=2C=C(CO)C=CC=2)C=2C(N)=NC=NC=2N1CC=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 RBPYUIYVYGSPKB-UHFFFAOYSA-N 0.000 claims 1
- JMBFPBNTNUTDLF-UHFFFAOYSA-N 3-(2-fluorophenyl)-2-[(7h-purin-6-ylamino)methyl]chromen-4-one Chemical compound FC1=CC=CC=C1C(C(C1=CC=CC=C1O1)=O)=C1CNC1=NC=NC2=C1N=CN2 JMBFPBNTNUTDLF-UHFFFAOYSA-N 0.000 claims 1
- LEMBJTYNTQDECJ-GFCCVEGCSA-N 3-(3-fluorophenyl)-2-[(1r)-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=CC=C2C(=O)C=1C1=CC=CC(F)=C1 LEMBJTYNTQDECJ-GFCCVEGCSA-N 0.000 claims 1
- LEMBJTYNTQDECJ-LBPRGKRZSA-N 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=CC=C2C(=O)C=1C1=CC=CC(F)=C1 LEMBJTYNTQDECJ-LBPRGKRZSA-N 0.000 claims 1
- PZXRCHLNYKHQSM-UHFFFAOYSA-N 3-(3-fluorophenyl)-2-[(7h-purin-6-ylamino)methyl]chromen-4-one Chemical compound FC1=CC=CC(C=2C(C3=CC=CC=C3OC=2CNC=2C=3N=CNC=3N=CN=2)=O)=C1 PZXRCHLNYKHQSM-UHFFFAOYSA-N 0.000 claims 1
- ZGGXQXLFNHDLLG-UHFFFAOYSA-N 3-(4-fluorophenyl)-2-(morpholin-4-ylmethyl)chromen-4-one Chemical compound C1=CC(F)=CC=C1C(C(C1=CC=CC=C1O1)=O)=C1CN1CCOCC1 ZGGXQXLFNHDLLG-UHFFFAOYSA-N 0.000 claims 1
- ITWLQBZRKIGAQY-UHFFFAOYSA-N 3-(4-fluorophenyl)-2-(morpholin-4-ylmethyl)chromen-4-one;hydrochloride Chemical compound Cl.C1=CC(F)=CC=C1C(C(C1=CC=CC=C1O1)=O)=C1CN1CCOCC1 ITWLQBZRKIGAQY-UHFFFAOYSA-N 0.000 claims 1
- SRPWHIILKXGVEP-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-(3-fluorophenyl)-4-oxochromen-2-yl]ethyl]pyrazolo[3,4-d]pyrimidin-3-yl]-n-cyclopropylbenzamide Chemical compound N1=C(C=2C=C(C=CC=2)C(=O)NC2CC2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 SRPWHIILKXGVEP-UHFFFAOYSA-N 0.000 claims 1
- YDAVFGOHSKDPLG-UHFFFAOYSA-N 3-phenyl-2-(7h-purin-6-ylsulfanylmethyl)chromen-4-one Chemical compound N=1C=NC=2NC=NC=2C=1SCC=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 YDAVFGOHSKDPLG-UHFFFAOYSA-N 0.000 claims 1
- OLCAEQPPVVYASY-ZDUSSCGKSA-N 3-phenyl-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=CC=C2C(=O)C=1C1=CC=CC=C1 OLCAEQPPVVYASY-ZDUSSCGKSA-N 0.000 claims 1
- XUHCZJLBWDGYEN-UHFFFAOYSA-N 3-phenyl-2-[(7h-purin-6-ylamino)methyl]chromen-4-one Chemical compound N=1C=NC=2NC=NC=2C=1NCC=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 XUHCZJLBWDGYEN-UHFFFAOYSA-N 0.000 claims 1
- XIVKKHYUECKZLP-UHFFFAOYSA-N 4-[4-amino-1-[1-[3-(3-fluorophenyl)-4-oxochromen-2-yl]ethyl]pyrazolo[3,4-d]pyrimidin-3-yl]thiophene-2-carbaldehyde Chemical compound N1=C(C=2C=C(C=O)SC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 XIVKKHYUECKZLP-UHFFFAOYSA-N 0.000 claims 1
- FBQFWYFUWNBDDW-UHFFFAOYSA-N 5-[4-amino-1-[1-[3-(3-fluorophenyl)-4-oxochromen-2-yl]ethyl]pyrazolo[3,4-d]pyrimidin-3-yl]furan-2-carbaldehyde Chemical compound N1=C(C=2OC(C=O)=CC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 FBQFWYFUWNBDDW-UHFFFAOYSA-N 0.000 claims 1
- OYSBUVSXKYYNMA-UHFFFAOYSA-N 6-bromo-2-(morpholin-4-ylmethyl)-3-phenylchromen-4-one Chemical compound C=1C=CC=CC=1C=1C(=O)C2=CC(Br)=CC=C2OC=1CN1CCOCC1 OYSBUVSXKYYNMA-UHFFFAOYSA-N 0.000 claims 1
- BSTWHUYNOKXPGL-UHFFFAOYSA-N 6-bromo-2-(morpholin-4-ylmethyl)-3-phenylchromen-4-one;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C=1C(=O)C2=CC(Br)=CC=C2OC=1CN1CCOCC1 BSTWHUYNOKXPGL-UHFFFAOYSA-N 0.000 claims 1
- ZAESDLHDSRHLOH-UHFFFAOYSA-N 6-bromo-2-[(4-methylbenzimidazol-1-yl)methyl]-3-phenylchromen-4-one Chemical compound C1=NC=2C(C)=CC=CC=2N1CC=1OC2=CC=C(Br)C=C2C(=O)C=1C1=CC=CC=C1 ZAESDLHDSRHLOH-UHFFFAOYSA-N 0.000 claims 1
- GGIZECDKZRRWPN-UHFFFAOYSA-N 6-bromo-2-[(6-chloropurin-9-yl)methyl]-3-phenylchromen-4-one Chemical compound C1=NC=2C(Cl)=NC=NC=2N1CC=1OC2=CC=C(Br)C=C2C(=O)C=1C1=CC=CC=C1 GGIZECDKZRRWPN-UHFFFAOYSA-N 0.000 claims 1
- XDWRULCXHCXHRP-UHFFFAOYSA-N 6-bromo-3-(4-fluorophenyl)-2-(morpholin-4-ylmethyl)chromen-4-one Chemical compound C1=CC(F)=CC=C1C(C(C1=CC(Br)=CC=C1O1)=O)=C1CN1CCOCC1 XDWRULCXHCXHRP-UHFFFAOYSA-N 0.000 claims 1
- OKNVSGNYSNPIPD-UHFFFAOYSA-N 6-bromo-3-(4-fluorophenyl)-2-(morpholin-4-ylmethyl)chromen-4-one;hydrochloride Chemical compound Cl.C1=CC(F)=CC=C1C(C(C1=CC(Br)=CC=C1O1)=O)=C1CN1CCOCC1 OKNVSGNYSNPIPD-UHFFFAOYSA-N 0.000 claims 1
- UWJUUEHCNSBZSK-UHFFFAOYSA-N 6-bromo-3-phenyl-2-(7h-purin-6-ylsulfanylmethyl)chromen-4-one Chemical compound O=C1C2=CC(Br)=CC=C2OC(CSC=2C=3N=CNC=3N=CN=2)=C1C1=CC=CC=C1 UWJUUEHCNSBZSK-UHFFFAOYSA-N 0.000 claims 1
- CCDVYDSKPOSJQL-LBPRGKRZSA-N 6-bromo-3-phenyl-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(Br)C=C2C(=O)C=1C1=CC=CC=C1 CCDVYDSKPOSJQL-LBPRGKRZSA-N 0.000 claims 1
- KXSDOBIWKOBINP-UHFFFAOYSA-N 6-bromo-3-phenyl-2-[(7h-purin-6-ylamino)methyl]chromen-4-one Chemical compound O=C1C2=CC(Br)=CC=C2OC(CNC=2C=3N=CNC=3N=CN=2)=C1C1=CC=CC=C1 KXSDOBIWKOBINP-UHFFFAOYSA-N 0.000 claims 1
- ZXRCPILJODBCHJ-LLVKDONJSA-N 6-fluoro-3-(3-fluorophenyl)-2-[(1r)-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-LLVKDONJSA-N 0.000 claims 1
- 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 1
- OQRJJNURZCEMKL-UHFFFAOYSA-N 6-fluoro-3-(3-fluorophenyl)-2-[(7h-purin-6-ylamino)methyl]chromen-4-one Chemical compound FC1=CC=CC(C=2C(C3=CC(F)=CC=C3OC=2CNC=2C=3N=CNC=3N=CN=2)=O)=C1 OQRJJNURZCEMKL-UHFFFAOYSA-N 0.000 claims 1
- JDTCSOLTCLBMKS-UHFFFAOYSA-N 6-fluoro-3-(3-fluorophenyl)-2-[1-(4-methoxyanilino)ethyl]chromen-4-one Chemical compound C1=CC(OC)=CC=C1NC(C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC(F)=CC=C2O1 JDTCSOLTCLBMKS-UHFFFAOYSA-N 0.000 claims 1
- YUSZXLCDUDCZGL-LBPRGKRZSA-N 6-fluoro-3-phenyl-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=C1 YUSZXLCDUDCZGL-LBPRGKRZSA-N 0.000 claims 1
- YJMCRCOUOLVLCD-UHFFFAOYSA-N 6-fluoro-3-phenyl-2-[(7h-purin-6-ylamino)methyl]chromen-4-one Chemical compound O=C1C2=CC(F)=CC=C2OC(CNC=2C=3N=CNC=3N=CN=2)=C1C1=CC=CC=C1 YJMCRCOUOLVLCD-UHFFFAOYSA-N 0.000 claims 1
- AEVVTGILFZUVRU-UHFFFAOYSA-N 7-[(6-bromo-4-oxo-3-phenylchromen-2-yl)methyl]-1,3-dimethylpurine-2,6-dione Chemical compound C1=2C(=O)N(C)C(=O)N(C)C=2N=CN1CC=1OC2=CC=C(Br)C=C2C(=O)C=1C1=CC=CC=C1 AEVVTGILFZUVRU-UHFFFAOYSA-N 0.000 claims 1
- 208000030507 AIDS Diseases 0.000 claims 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- LSBDFXRDZJMBSC-UHFFFAOYSA-N Amide-Phenylacetic acid Natural products NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims 1
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 1
- 206010003571 Astrocytoma Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 208000030767 Autoimmune encephalitis Diseases 0.000 claims 1
- 206010003827 Autoimmune hepatitis Diseases 0.000 claims 1
- 206010050245 Autoimmune thrombocytopenia Diseases 0.000 claims 1
- 208000023514 Barrett esophagus Diseases 0.000 claims 1
- 208000023328 Basedow disease Diseases 0.000 claims 1
- 208000009137 Behcet syndrome Diseases 0.000 claims 1
- 206010005003 Bladder cancer Diseases 0.000 claims 1
- 208000006386 Bone Resorption Diseases 0.000 claims 1
- 208000020084 Bone disease Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 208000011691 Burkitt lymphomas Diseases 0.000 claims 1
- 208000010667 Carcinoma of liver and intrahepatic biliary tract Diseases 0.000 claims 1
- 208000031229 Cardiomyopathies Diseases 0.000 claims 1
- 206010008342 Cervix carcinoma Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 201000003883 Cystic fibrosis Diseases 0.000 claims 1
- 208000016192 Demyelinating disease Diseases 0.000 claims 1
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- 208000010334 End Stage Liver Disease Diseases 0.000 claims 1
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims 1
- 201000008808 Fibrosarcoma Diseases 0.000 claims 1
- 208000022072 Gallbladder Neoplasms Diseases 0.000 claims 1
- 208000007465 Giant cell arteritis Diseases 0.000 claims 1
- 208000032612 Glial tumor Diseases 0.000 claims 1
- 206010018338 Glioma Diseases 0.000 claims 1
- 206010018364 Glomerulonephritis Diseases 0.000 claims 1
- 208000009329 Graft vs Host Disease Diseases 0.000 claims 1
- 206010018691 Granuloma Diseases 0.000 claims 1
- 208000015023 Graves' disease Diseases 0.000 claims 1
- 208000030836 Hashimoto thyroiditis Diseases 0.000 claims 1
- 206010073069 Hepatic cancer Diseases 0.000 claims 1
- 208000003923 Hereditary Corneal Dystrophies Diseases 0.000 claims 1
- 206010062639 Herpes dermatitis Diseases 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 208000005615 Interstitial Cystitis Diseases 0.000 claims 1
- 208000007766 Kaposi sarcoma Diseases 0.000 claims 1
- 206010024229 Leprosy Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 201000009906 Meningitis Diseases 0.000 claims 1
- 208000034578 Multiple myelomas Diseases 0.000 claims 1
- 201000002481 Myositis Diseases 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- LIKGCNJQMKWKIZ-UHFFFAOYSA-N NC1=C2C(=NC=N1)N(N=C2C2=CC(=C(C(=C2)OC)OC)OC)C(C)C=2OC1=CC=CC=C1C(C2C2=CC(=CC=C2)F)=O Chemical compound NC1=C2C(=NC=N1)N(N=C2C2=CC(=C(C(=C2)OC)OC)OC)C(C)C=2OC1=CC=CC=C1C(C2C2=CC(=CC=C2)F)=O LIKGCNJQMKWKIZ-UHFFFAOYSA-N 0.000 claims 1
- AUXRILMOCUSGMO-UHFFFAOYSA-N NC1=C2C(=NC=N1)N(N=C2C=2CC(C=CC2)(OC)F)C(C)C=2OC1=CC=CC=C1C(C2C2=CC(=CC=C2)F)=O Chemical compound NC1=C2C(=NC=N1)N(N=C2C=2CC(C=CC2)(OC)F)C(C)C=2OC1=CC=CC=C1C(C2C2=CC(=CC=C2)F)=O AUXRILMOCUSGMO-UHFFFAOYSA-N 0.000 claims 1
- 206010029164 Nephrotic syndrome Diseases 0.000 claims 1
- 206010029260 Neuroblastoma Diseases 0.000 claims 1
- 206010030155 Oesophageal carcinoma Diseases 0.000 claims 1
- 241000243985 Onchocerca volvulus Species 0.000 claims 1
- 208000001132 Osteoporosis Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010053869 POEMS syndrome Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 201000011152 Pemphigus Diseases 0.000 claims 1
- 208000031845 Pernicious anaemia Diseases 0.000 claims 1
- 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 claims 1
- 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 206010010180 Renal failure complications Diseases 0.000 claims 1
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- 206010039710 Scleroderma Diseases 0.000 claims 1
- 201000010208 Seminoma Diseases 0.000 claims 1
- 208000021386 Sjogren Syndrome Diseases 0.000 claims 1
- 208000000453 Skin Neoplasms Diseases 0.000 claims 1
- 206010041067 Small cell lung cancer Diseases 0.000 claims 1
- 208000004346 Smoldering Multiple Myeloma Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 206010042742 Sympathetic ophthalmia Diseases 0.000 claims 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 claims 1
- 208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 claims 1
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 1
- 206010046851 Uveitis Diseases 0.000 claims 1
- 206010046914 Vaginal infection Diseases 0.000 claims 1
- 201000008100 Vaginitis Diseases 0.000 claims 1
- 241000700605 Viruses Species 0.000 claims 1
- 206010047642 Vitiligo Diseases 0.000 claims 1
- 201000006083 Xeroderma Pigmentosum Diseases 0.000 claims 1
- 230000001919 adrenal effect Effects 0.000 claims 1
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 1
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 1
- 208000002205 allergic conjunctivitis Diseases 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 230000000735 allogeneic effect Effects 0.000 claims 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 1
- 229940035676 analgesics Drugs 0.000 claims 1
- 230000001387 anti-histamine Effects 0.000 claims 1
- 229940125715 antihistaminic agent Drugs 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims 1
- 208000024998 atopic conjunctivitis Diseases 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 230000001363 autoimmune Effects 0.000 claims 1
- 201000004982 autoimmune uveitis Diseases 0.000 claims 1
- 201000001531 bladder carcinoma Diseases 0.000 claims 1
- 230000024279 bone resorption Effects 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 208000029028 brain injury Diseases 0.000 claims 1
- 201000008275 breast carcinoma Diseases 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 210000003169 central nervous system Anatomy 0.000 claims 1
- 201000010881 cervical cancer Diseases 0.000 claims 1
- 208000011444 chronic liver failure Diseases 0.000 claims 1
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims 1
- 206010009887 colitis Diseases 0.000 claims 1
- 206010011005 corneal dystrophy Diseases 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 201000002491 encephalomyelitis Diseases 0.000 claims 1
- 206010014801 endophthalmitis Diseases 0.000 claims 1
- 201000004101 esophageal cancer Diseases 0.000 claims 1
- 201000006569 extramedullary plasmacytoma Diseases 0.000 claims 1
- 230000003325 follicular Effects 0.000 claims 1
- 201000010175 gallbladder cancer Diseases 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 208000007565 gingivitis Diseases 0.000 claims 1
- 208000024908 graft versus host disease Diseases 0.000 claims 1
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims 1
- 208000009326 ileitis Diseases 0.000 claims 1
- 201000001371 inclusion conjunctivitis Diseases 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 125000002346 iodo group Chemical group I* 0.000 claims 1
- 208000017169 kidney disease Diseases 0.000 claims 1
- 201000002250 liver carcinoma Diseases 0.000 claims 1
- 208000019423 liver disease Diseases 0.000 claims 1
- 201000005296 lung carcinoma Diseases 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 206010028417 myasthenia gravis Diseases 0.000 claims 1
- 208000031225 myocardial ischemia Diseases 0.000 claims 1
- 208000009928 nephrosis Diseases 0.000 claims 1
- 231100001027 nephrosis Toxicity 0.000 claims 1
- 210000000653 nervous system Anatomy 0.000 claims 1
- 208000007538 neurilemmoma Diseases 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 208000015270 non-secretory plasma cell myeloma Diseases 0.000 claims 1
- 208000002042 onchocerciasis Diseases 0.000 claims 1
- 210000000056 organ Anatomy 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 201000008968 osteosarcoma Diseases 0.000 claims 1
- 201000009234 osteosclerotic myeloma Diseases 0.000 claims 1
- 229940127084 other anti-cancer agent Drugs 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 201000001976 pemphigus vulgaris Diseases 0.000 claims 1
- 201000001245 periodontitis Diseases 0.000 claims 1
- 210000001428 peripheral nervous system Anatomy 0.000 claims 1
- 208000031223 plasma cell leukemia Diseases 0.000 claims 1
- 208000005987 polymyositis Diseases 0.000 claims 1
- 201000011461 pre-eclampsia Diseases 0.000 claims 1
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 1
- 230000000306 recurrent effect Effects 0.000 claims 1
- 201000010174 renal carcinoma Diseases 0.000 claims 1
- 201000009410 rhabdomyosarcoma Diseases 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 206010039667 schwannoma Diseases 0.000 claims 1
- 201000000849 skin cancer Diseases 0.000 claims 1
- 208000000587 small cell lung carcinoma Diseases 0.000 claims 1
- 208000010721 smoldering plasma cell myeloma Diseases 0.000 claims 1
- 208000020431 spinal cord injury Diseases 0.000 claims 1
- 206010041823 squamous cell carcinoma Diseases 0.000 claims 1
- 238000010186 staining Methods 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 206010043207 temporal arteritis Diseases 0.000 claims 1
- 208000001608 teratocarcinoma Diseases 0.000 claims 1
- HWCXSZZGMROORD-UHFFFAOYSA-N tert-butyl n-[[5-[4-amino-1-[1-[3-(3-fluorophenyl)-4-oxochromen-2-yl]ethyl]pyrazolo[3,4-d]pyrimidin-3-yl]thiophen-2-yl]methyl]carbamate Chemical compound N1=C(C=2SC(CNC(=O)OC(C)(C)C)=CC=2)C2=C(N)N=CN=C2N1C(C)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 HWCXSZZGMROORD-UHFFFAOYSA-N 0.000 claims 1
- 210000001550 testis Anatomy 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 201000002510 thyroid cancer Diseases 0.000 claims 1
- 210000001685 thyroid gland Anatomy 0.000 claims 1
- 206010043778 thyroiditis Diseases 0.000 claims 1
- 206010044325 trachoma Diseases 0.000 claims 1
- 238000002054 transplantation Methods 0.000 claims 1
- 201000008827 tuberculosis Diseases 0.000 claims 1
- 208000010570 urinary bladder carcinoma Diseases 0.000 claims 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN2690/CHE/2009 | 2009-11-05 | ||
| IN2690CH2009 | 2009-11-05 | ||
| IN1429CH2010 | 2010-05-24 | ||
| IN1429/CHE/2010 | 2010-05-24 | ||
| US36466110P | 2010-07-15 | 2010-07-15 | |
| US61/364,661 | 2010-07-15 | ||
| PCT/IB2010/002804 WO2011055215A2 (en) | 2009-11-05 | 2010-11-03 | Novel kinase modulators |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016027735A Division JP6385966B2 (ja) | 2009-11-05 | 2016-02-17 | 新規キナーゼモジュレーター |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013510133A JP2013510133A (ja) | 2013-03-21 |
| JP2013510133A5 true JP2013510133A5 (OSRAM) | 2013-12-26 |
| JP5889795B2 JP5889795B2 (ja) | 2016-03-22 |
Family
ID=43970461
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012537454A Active JP5889795B2 (ja) | 2009-11-05 | 2010-11-03 | 新規キナーゼモジュレーター |
| JP2016027735A Expired - Fee Related JP6385966B2 (ja) | 2009-11-05 | 2016-02-17 | 新規キナーゼモジュレーター |
| JP2018079763A Pending JP2018111727A (ja) | 2009-11-05 | 2018-04-18 | 新規キナーゼモジュレーター |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016027735A Expired - Fee Related JP6385966B2 (ja) | 2009-11-05 | 2016-02-17 | 新規キナーゼモジュレーター |
| JP2018079763A Pending JP2018111727A (ja) | 2009-11-05 | 2018-04-18 | 新規キナーゼモジュレーター |
Country Status (30)
| Country | Link |
|---|---|
| US (7) | US10442783B2 (OSRAM) |
| EP (3) | EP3050876A3 (OSRAM) |
| JP (3) | JP5889795B2 (OSRAM) |
| KR (2) | KR102012398B1 (OSRAM) |
| CN (2) | CN102812013B (OSRAM) |
| AP (1) | AP2012006294A0 (OSRAM) |
| AU (2) | AU2010316780B2 (OSRAM) |
| BR (1) | BR112012010640A2 (OSRAM) |
| CA (2) | CA2779574C (OSRAM) |
| CO (1) | CO6551721A2 (OSRAM) |
| CY (1) | CY1119766T1 (OSRAM) |
| DK (1) | DK2496567T3 (OSRAM) |
| EA (2) | EA036876B1 (OSRAM) |
| ES (1) | ES2651682T3 (OSRAM) |
| HR (1) | HRP20171537T1 (OSRAM) |
| HU (1) | HUE035059T2 (OSRAM) |
| IL (1) | IL219585A (OSRAM) |
| LT (1) | LT2496567T (OSRAM) |
| MX (1) | MX352661B (OSRAM) |
| MY (1) | MY173795A (OSRAM) |
| NZ (1) | NZ599830A (OSRAM) |
| PH (2) | PH12012500901A1 (OSRAM) |
| PL (1) | PL2496567T3 (OSRAM) |
| PT (1) | PT2496567T (OSRAM) |
| RS (1) | RS56432B1 (OSRAM) |
| SG (1) | SG10201500895XA (OSRAM) |
| SI (1) | SI2496567T1 (OSRAM) |
| SM (1) | SMT201700468T1 (OSRAM) |
| WO (1) | WO2011055215A2 (OSRAM) |
| ZA (1) | ZA201203849B (OSRAM) |
Families Citing this family (72)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2725014C (en) | 2008-05-30 | 2014-06-17 | Amgen Inc. | Inhibitors of pi3 kinase |
| EP2448938B9 (en) | 2009-06-29 | 2015-06-10 | Incyte Corporation | Pyrimidinones as pi3k inhibitors |
| KR102263079B1 (ko) * | 2009-11-05 | 2021-06-10 | 리젠 파마슈티컬스 소시에떼 아노님 | 신규한 벤조피란 키나제 조절제 |
| AP2012006294A0 (en) | 2009-11-05 | 2012-06-30 | Rhizen Pharmaceuticals Sa | Novel kinase modulators. |
| US8759359B2 (en) | 2009-12-18 | 2014-06-24 | Incyte Corporation | Substituted heteroaryl fused derivatives as PI3K inhibitors |
| AR081823A1 (es) | 2010-04-14 | 2012-10-24 | Incyte Corp | DERIVADOS FUSIONADOS COMO INHIBIDORES DE PI3Kd |
| US9062055B2 (en) | 2010-06-21 | 2015-06-23 | Incyte Corporation | Fused pyrrole derivatives as PI3K inhibitors |
| EP2655374B1 (en) | 2010-12-20 | 2019-10-23 | Incyte Holdings Corporation | N-(1-(substituted-phenyl)ethyl)-9h-purin-6-amines as pi3k inhibitors |
| US9108984B2 (en) | 2011-03-14 | 2015-08-18 | Incyte Corporation | Substituted diamino-pyrimidine and diamino-pyridine derivatives as PI3K inhibitors |
| US9126948B2 (en) | 2011-03-25 | 2015-09-08 | Incyte Holdings Corporation | Pyrimidine-4,6-diamine derivatives as PI3K inhibitors |
| DK2705029T3 (en) * | 2011-05-04 | 2019-02-18 | Rhizen Pharmaceuticals S A | Hitherto UNKNOWN RELATIONS AS MODULATORS OF PROTEIN KINASES |
| AU2012283775A1 (en) | 2011-07-13 | 2014-01-23 | Pharmacyclics Llc | Inhibitors of Bruton's tyrosine kinase |
| PL3513793T3 (pl) | 2011-09-02 | 2021-09-20 | Incyte Holdings Corporation | Heterocykloaminy jako inhibitory pi3k |
| US20150011569A1 (en) * | 2011-12-15 | 2015-01-08 | Philadelphia Health & Education Corporation D/B/A Drexel University College Of Medicine | NOVEL P13K p110 INHIBITORS AND METHODS OF USE THEREOF |
| DK2790705T3 (en) | 2011-12-15 | 2018-03-12 | Novartis Ag | Use of inhibitors of the activity or function of PI3K |
| KR102109992B1 (ko) * | 2012-03-23 | 2020-05-13 | 피티씨 테라퓨틱스, 인크. | 척수성 근위축증을 치료하기 위한 화합물 |
| AR090548A1 (es) | 2012-04-02 | 2014-11-19 | Incyte Corp | Azaheterociclobencilaminas biciclicas como inhibidores de pi3k |
| PL2844647T3 (pl) * | 2012-05-04 | 2021-01-25 | Rhizen Pharmaceuticals S.A. | Nowy sposób wytwarzania czystych optycznie i opcjonalnie podstawionych pochodnych 2-(1-hydroksyalkilo)-chromen-4-onu i ich zastosowanie do wytwarzania środków farmaceutycznych |
| US10130635B2 (en) | 2012-05-04 | 2018-11-20 | Rhizen Pharmaceuticals Sa | Process for preparation of optically pure and optionally substituted 2-(1-hydroxy-alkyl)-chromen-4-one derivatives and their use in preparing pharmaceuticals |
| MX357043B (es) * | 2012-07-04 | 2018-06-25 | Rhizen Pharmaceuticals Sa | Inhibidores selectivos de pi3k delta. |
| US9512119B2 (en) * | 2012-07-27 | 2016-12-06 | Sato Pharmaceutical Co., Ltd. | Difluoromethylene compound |
| US20150258127A1 (en) * | 2012-10-31 | 2015-09-17 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for preventing antiphospholipid syndrome (aps) |
| EP3756686A1 (en) | 2012-11-02 | 2020-12-30 | TG Therapeutics Inc. | Combination of anti-cd20 antibody and pi3 kinase selective inhibitor |
| US9737521B2 (en) | 2012-11-08 | 2017-08-22 | Rhizen Pharmaceuticals Sa | Pharmaceutical compositions containing a PDE4 inhibitor and a PI3 delta or dual PI3 delta-gamma kinase inhibitor |
| SG11201509992RA (en) * | 2013-06-07 | 2016-01-28 | Rhizen Pharmaceuticals Sa | Dual selective pi3 delta and gamma kinase inhibitors |
| US11352359B2 (en) * | 2013-07-02 | 2022-06-07 | Rhizen Pharmaceuticals Ag | PI3K protein kinase inhibitors |
| AR098776A1 (es) * | 2013-12-18 | 2016-06-15 | Chiesi Farm Spa | Derivados del isocromeno como inhibidores de las fosfoinositido-3 quinasas |
| CN105960405B (zh) * | 2014-01-06 | 2021-02-19 | 理森制药股份公司 | 谷氨酰胺酶抑制剂 |
| WO2015191677A1 (en) | 2014-06-11 | 2015-12-17 | Incyte Corporation | Bicyclic heteroarylaminoalkyl phenyl derivatives as pi3k inhibitors |
| DK3160968T3 (en) | 2014-06-27 | 2019-02-18 | Rhizen Pharmaceuticals S A | SUBSTITUTED CHROMINE DERIVATIVES AS SELECTIVE DOUBLE INHIBITORS OF PI3 DELTA AND GAMMA PROTEIN KINASES |
| CN105315252A (zh) * | 2014-07-03 | 2016-02-10 | 中国药科大学 | 基于3-羟基色原酮结构的Raf激酶抑制剂及其制备方法和用途 |
| MA40250A (fr) | 2014-07-04 | 2017-05-10 | Lupin Ltd | Dérivés de quinolizinone utilisés comme inhibiteurs de pi3k |
| BR112017004163A2 (pt) | 2014-09-03 | 2017-12-05 | Rhizen Pharmaceuticals Sa | método de tratamento e composições com um inibidor de quinase pi3k delta e gamma duplo e um corticostoide |
| US9950194B2 (en) | 2014-09-09 | 2018-04-24 | Mevion Medical Systems, Inc. | Patient positioning system |
| RS63963B1 (sr) | 2015-02-27 | 2023-03-31 | Incyte Holdings Corp | Postupak pripreme pi3k inhibitora |
| CN106008479B (zh) * | 2015-03-06 | 2020-01-10 | 南京圣和药业股份有限公司 | 作为磷脂酰肌醇3-激酶δ抑制剂的取代嘧啶类化合物及其应用 |
| US9968604B2 (en) * | 2015-04-16 | 2018-05-15 | Chiesi Farmaceutici S.P.A. | Chromene derivatives as phoshoinositide 3-kinases inhibitors |
| GB201506786D0 (en) * | 2015-04-21 | 2015-06-03 | Ucb Biopharma Sprl | Therapeutic use |
| WO2016183063A1 (en) | 2015-05-11 | 2016-11-17 | Incyte Corporation | Crystalline forms of a pi3k inhibitor |
| US9732097B2 (en) | 2015-05-11 | 2017-08-15 | Incyte Corporation | Process for the synthesis of a phosphoinositide 3-kinase inhibitor |
| JP2018521044A (ja) * | 2015-07-23 | 2018-08-02 | ファーマケア，インク． | リシルオキシダーゼ様２阻害剤とその使用 |
| JP2019508400A (ja) | 2016-02-09 | 2019-03-28 | ファーマケア，インク． | キノリノンリシルオキシダーゼ様２阻害剤とその使用 |
| GB201602527D0 (en) * | 2016-02-12 | 2016-03-30 | Glaxosmithkline Ip Dev Ltd | Chemical compounds |
| PT3442535T (pt) | 2016-04-15 | 2022-09-05 | Cancer Research Tech Ltd | Compostos heterocíclicos como inibidores da ret quinase |
| RS62322B1 (sr) | 2016-04-15 | 2021-10-29 | Cancer Research Tech Ltd | Heterociklična jedinjenja kao inhibitori ret kinaze |
| MX2018014577A (es) | 2016-05-27 | 2019-05-20 | Tg Therapeutics Inc | Combinacion de anticuerpo anti-cd20, inhibidor selectivo de quinasa p13-delta, e inhibidor de btk para tratar trastornos proliferativos de celulas b. |
| EP3509634A1 (en) | 2016-09-09 | 2019-07-17 | TG Therapeutics Inc. | Combination of an anti-cd20 antibody, pi3 kinase-delta inhibitor, and anti-pd-1 or anti-pd-l1 antibody for treating hematological cancers |
| CN110267960B (zh) | 2017-01-18 | 2022-04-26 | 阿雷生物药品公司 | 作为RET激酶抑制剂的取代的吡唑并[1,5-a]吡嗪化合物 |
| GB201705971D0 (en) | 2017-04-13 | 2017-05-31 | Cancer Res Tech Ltd | Inhibitor compounds |
| CN111770776A (zh) * | 2017-12-06 | 2020-10-13 | 瑞真药业公司 | 治疗外周t细胞淋巴瘤和皮肤t细胞淋巴瘤的组合物和方法 |
| WO2019143994A1 (en) * | 2018-01-18 | 2019-07-25 | Array Biopharma Inc. | Substituted pyrazolyl[4,3-c]pyridinecompounds as ret kinase inhibitors |
| TW201938169A (zh) * | 2018-01-18 | 2019-10-01 | 美商亞雷生物製藥股份有限公司 | 作為RET激酶抑制劑之經取代吡唑并[3,4-d]嘧啶化合物 |
| CN111971286B (zh) * | 2018-01-18 | 2023-04-14 | 阿雷生物药品公司 | 作为RET激酶抑制剂的取代的吡咯并[2,3-d]嘧啶化合物 |
| AU2019277560B2 (en) | 2018-06-01 | 2025-04-24 | Incyte Corporation | Dosing regimen for the treatment of PI3K related disorders |
| EP3828184A4 (en) * | 2018-08-21 | 2022-05-04 | Medshine Discovery Inc. | PYRAZOLOPYRIMIDI DERIVATIVES AND USE THEREOF AS A PI3K INHIBITOR |
| ES2922314T3 (es) | 2018-09-10 | 2022-09-13 | Array Biopharma Inc | Compuestos heterocíclicos condensados como inhibidores de cinasa RET |
| WO2021198283A1 (en) * | 2020-03-31 | 2021-10-07 | Janssen Pharmaceutica Nv | Inhibitors of antigen presentation by hla-dr |
| AR121719A1 (es) * | 2020-04-03 | 2022-06-29 | Petra Pharma Corp | Inhibidores alostéricos de cromenona del fosfoinosítido 3-quinasa (pi3k) para el tratamiento de enfermedades |
| US12428422B2 (en) | 2020-05-14 | 2025-09-30 | Rhizen Pharmaceuticals Ag | Purine derivatives as SIK-3 inhibitors |
| CN111499619B (zh) * | 2020-05-20 | 2021-05-18 | 温州医科大学附属第一医院 | 一种治疗肝纤维化的药物及其制备方法 |
| US20220143026A1 (en) | 2020-11-12 | 2022-05-12 | Tg Therapeutics, Inc. | Triple combination to treat b-cell malignancies |
| CN113337457B (zh) * | 2021-06-01 | 2024-06-25 | 澳门大学 | 一种无血清调控干细胞的细胞状态的方法以及调节剂的应用 |
| TW202328132A (zh) * | 2021-12-31 | 2023-07-16 | 大陸商同潤生物醫藥(上海)有限公司 | ＰＩ３Ｋδ／γ雙重抑制劑化合物的半富馬酸鹽結晶及其製備方法 |
| CN116410194B (zh) * | 2021-12-31 | 2025-07-18 | 同润生物医药(上海)有限公司 | 一种苯磺酸盐结晶及其制备方法 |
| WO2023130334A1 (zh) * | 2022-01-07 | 2023-07-13 | 同润生物医药(上海)有限公司 | 一种色烯-4-酮化合物及其中间体的制备方法 |
| CN116444521A (zh) * | 2022-01-07 | 2023-07-18 | 同润生物医药(上海)有限公司 | 一种色烯-4-酮化合物及其中间体的制备方法 |
| CN114891005B (zh) * | 2022-03-30 | 2024-01-19 | 武汉九州钰民医药科技有限公司 | 一种乌帕利斯对甲苯磺酸盐的制备工艺 |
| US11884740B1 (en) | 2022-06-01 | 2024-01-30 | Tg Therapeutics, Inc. | Anti-CD20 antibody compositions |
| US11965032B1 (en) | 2022-06-01 | 2024-04-23 | Tg Therapeutics, Inc. | Anti-CD20 antibody compositions |
| US11814439B1 (en) | 2022-06-01 | 2023-11-14 | Tg Therapeutics, Inc. | Anti-CD20 antibody compositions |
| US11807689B1 (en) | 2022-06-01 | 2023-11-07 | Tg Therapeutics, Inc. | Anti-CD20 antibody compositions |
| WO2024192309A1 (en) * | 2023-03-15 | 2024-09-19 | Reactive Biosciences, Inc. | Chemical compounds |
Family Cites Families (129)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1223531A (fr) * | 1959-01-29 | 1960-06-17 | Rech S & Documentation Chimiqu | Application des oxalates d'aryle à un nouveau mode de préparation des esters gamma-benzopyrone-2-carboxyliques |
| US3691016A (en) | 1970-04-17 | 1972-09-12 | Monsanto Co | Process for the preparation of insoluble enzymes |
| CA1023287A (en) | 1972-12-08 | 1977-12-27 | Boehringer Mannheim G.M.B.H. | Process for the preparation of carrier-bound proteins |
| US4179337A (en) | 1973-07-20 | 1979-12-18 | Davis Frank F | Non-immunogenic polypeptides |
| JPS5126877A (ja) * | 1974-08-21 | 1976-03-05 | Tanabe Seiyaku Co | Shinkikisantonjudotaino seiho |
| US4195128A (en) | 1976-05-03 | 1980-03-25 | Bayer Aktiengesellschaft | Polymeric carrier bound ligands |
| US4330440A (en) | 1977-02-08 | 1982-05-18 | Development Finance Corporation Of New Zealand | Activated matrix and method of activation |
| CA1093991A (en) | 1977-02-17 | 1981-01-20 | Hideo Hirohara | Enzyme immobilization with pullulan gel |
| US4229537A (en) | 1978-02-09 | 1980-10-21 | New York University | Preparation of trichloro-s-triazine activated supports for coupling ligands |
| US4289872A (en) | 1979-04-06 | 1981-09-15 | Allied Corporation | Macromolecular highly branched homogeneous compound based on lysine units |
| JPS6023084B2 (ja) | 1979-07-11 | 1985-06-05 | 味の素株式会社 | 代用血液 |
| US4640835A (en) | 1981-10-30 | 1987-02-03 | Nippon Chemiphar Company, Ltd. | Plasminogen activator derivatives |
| FR2516922A1 (fr) | 1981-11-25 | 1983-05-27 | Lipha | Acides (oxo-4-4h-(1)-benzopyran-8-yl) alcanoiques, sels et derives, preparation et medicament les contenant |
| US4496689A (en) | 1983-12-27 | 1985-01-29 | Miles Laboratories, Inc. | Covalently attached complex of alpha-1-proteinase inhibitor with a water soluble polymer |
| EP0206448B1 (en) | 1985-06-19 | 1990-11-14 | Ajinomoto Co., Inc. | Hemoglobin combined with a poly(alkylene oxide) |
| JPS62201882A (ja) | 1985-11-18 | 1987-09-05 | Yamanouchi Pharmaceut Co Ltd | イソフラボン誘導体 |
| AT386415B (de) | 1986-05-16 | 1988-08-25 | Greber Gerd | Verfahren zur herstellung von neuen loeslichen und/oder schmelzbaren polyimiden und polyamidimiden |
| US4791192A (en) | 1986-06-26 | 1988-12-13 | Takeda Chemical Industries, Ltd. | Chemically modified protein with polyethyleneglycol |
| NL8720442A (nl) | 1986-08-18 | 1989-04-03 | Clinical Technologies Ass | Afgeefsystemen voor farmacologische agentia. |
| US5229490A (en) | 1987-05-06 | 1993-07-20 | The Rockefeller University | Multiple antigen peptide system |
| GB8827305D0 (en) | 1988-11-23 | 1988-12-29 | British Bio Technology | Compounds |
| US5013556A (en) | 1989-10-20 | 1991-05-07 | Liposome Technology, Inc. | Liposomes with enhanced circulation time |
| JPH07505915A (ja) | 1992-04-14 | 1995-06-29 | コーネル リサーチ ファウンデーション、インコーポレーテッド | 樹枝状巨大分子およびその製造法 |
| US5646176A (en) | 1992-12-24 | 1997-07-08 | Bristol-Myers Squibb Company | Phosphonooxymethyl ethers of taxane derivatives |
| US5455258A (en) | 1993-01-06 | 1995-10-03 | Ciba-Geigy Corporation | Arylsulfonamido-substituted hydroxamic acids |
| JPH0817590A (ja) | 1994-06-28 | 1996-01-19 | Achilles Corp | 除電ロール |
| JPH08176070A (ja) | 1994-12-19 | 1996-07-09 | Mitsubishi Chem Corp | ジデプシド誘導体及びｐｉ３キナーゼ阻害剤 |
| JPH08175990A (ja) | 1994-12-19 | 1996-07-09 | Mitsubishi Chem Corp | Ｐｉ３キナーゼ阻害剤とその製造法 |
| US5863949A (en) | 1995-03-08 | 1999-01-26 | Pfizer Inc | Arylsulfonylamino hydroxamic acid derivatives |
| PT821671E (pt) | 1995-04-20 | 2001-04-30 | Pfizer | Derivados do acido arilsulfonil hidroxamico como inibidores de mmp e tnf |
| GB9521987D0 (en) | 1995-10-26 | 1996-01-03 | Ludwig Inst Cancer Res | Phosphoinositide 3-kinase modulators |
| ATE225343T1 (de) | 1995-12-20 | 2002-10-15 | Hoffmann La Roche | Matrix-metalloprotease inhibitoren |
| JP3195756B2 (ja) | 1996-07-04 | 2001-08-06 | 公子 吉水 | 潤滑補助体 |
| EP0818442A3 (en) | 1996-07-12 | 1998-12-30 | Pfizer Inc. | Cyclic sulphone derivatives as inhibitors of metalloproteinases and of the production of tumour necrosis factor |
| EP0923585B1 (en) | 1996-07-18 | 2002-05-08 | Pfizer Inc. | Phosphinate based inhibitors of matrix metalloproteases |
| IL128189A0 (en) | 1996-08-23 | 1999-11-30 | Pfizer | Arylsulfonylamino hydroxamic acid derivatives |
| IT1289154B1 (it) * | 1997-01-03 | 1998-09-29 | Chiesi Farma Spa | Derivati di isoflavone loro preparazione e loro impiego terapeutico |
| EP0950059B1 (en) | 1997-01-06 | 2004-08-04 | Pfizer Inc. | Cyclic sulfone derivatives |
| ATE248812T1 (de) | 1997-02-03 | 2003-09-15 | Pfizer Prod Inc | Arylsulfonylhydroxamsäurederivate |
| CA2279863A1 (en) | 1997-02-07 | 1998-08-13 | Pfizer Inc. | N-hydroxy-beta-sulfonyl-propionamide derivatives and their use as inhibitors of matrix metalloproteinases |
| TR199901926T2 (xx) | 1997-02-11 | 1999-12-21 | Pfizer Inc. | Arils�lfonil hidroksamik asit t�revleri |
| US6605599B1 (en) | 1997-07-08 | 2003-08-12 | Bristol-Myers Squibb Company | Epothilone derivatives |
| PT1003720E (pt) | 1997-08-08 | 2004-07-30 | Pfizer Prod Inc | Derivados de acido ariloxiarilsulfonilamino hidroxamico |
| GB9725782D0 (en) | 1997-12-05 | 1998-02-04 | Pfizer Ltd | Therapeutic agents |
| GB9801690D0 (en) | 1998-01-27 | 1998-03-25 | Pfizer Ltd | Therapeutic agents |
| JP4462654B2 (ja) | 1998-03-26 | 2010-05-12 | ソニー株式会社 | 映像素材選択装置及び映像素材選択方法 |
| PA8469501A1 (es) | 1998-04-10 | 2000-09-29 | Pfizer Prod Inc | Hidroxamidas del acido (4-arilsulfonilamino)-tetrahidropiran-4-carboxilico |
| PA8469401A1 (es) | 1998-04-10 | 2000-05-24 | Pfizer Prod Inc | Derivados biciclicos del acido hidroxamico |
| PT1004578E (pt) | 1998-11-05 | 2004-06-30 | Pfizer Prod Inc | Derivados hidroxamida do acido 5-oxo-pirrolidino-2-carboxilico |
| SK287200B6 (sk) | 1999-02-22 | 2010-03-08 | Gesellschaft Fuer Biotechnologische Forschung Mbh (Gbf) | C-21 modifikované epotilóny, spôsob ich prípravy, farmaceutický prostriedok s ich obsahom a použitie |
| US6750246B1 (en) | 2000-02-03 | 2004-06-15 | Bristol-Myers Squibb Company | C-4 carbonate taxanes |
| JP2001247477A (ja) | 2000-03-03 | 2001-09-11 | Teikoku Hormone Mfg Co Ltd | 抗腫瘍剤 |
| EP1278748B1 (en) | 2000-04-25 | 2011-03-23 | ICOS Corporation | Inhibitors of human phosphatidyl-inositol 3-kinase delta |
| US6403588B1 (en) | 2000-04-27 | 2002-06-11 | Yamanouchi Pharmaceutical Co., Ltd. | Imidazopyridine derivatives |
| US6608053B2 (en) | 2000-04-27 | 2003-08-19 | Yamanouchi Pharmaceutical Co., Ltd. | Fused heteroaryl derivatives |
| DE60203260T2 (de) | 2001-01-16 | 2006-02-02 | Glaxo Group Ltd., Greenford | Pharmazeutische kombination, die ein 4-chinazolinamin und paclitaxel, carboplatin oder vinorelbin enthält, zur behandlung von krebs |
| US20040242545A1 (en) | 2001-07-26 | 2004-12-02 | Santen Phamaceutical Co., Ltd. | Remedy for glaucoma comprising as the active ingredient compound having p13 kinase inhibitory effect |
| US6703414B2 (en) | 2001-09-14 | 2004-03-09 | Arizona Board Of Regents On Behalf Of The University Of Arizona | Device and method for treating restenosis |
| AU2002357667A1 (en) | 2001-10-24 | 2003-05-06 | Iconix Pharmaceuticals, Inc. | Modulators of phosphoinositide 3-kinase |
| US6908932B2 (en) | 2001-10-24 | 2005-06-21 | Iconix Pharmaceuticals, Inc. | Modulators of phosphoinositide 3-kinase |
| MXPA04004064A (es) | 2001-10-30 | 2004-09-06 | Pharmacia Corp | Derivados heteroaromaticos de carboxamida para el tratramiento de la inflamacion. |
| KR101052816B1 (ko) * | 2002-04-17 | 2011-07-29 | 스미스 클라인 비참 코포레이션 | 화합물, 조성물 및 방법 |
| AU2003255529B2 (en) | 2002-07-10 | 2008-11-20 | Laboratoires Serono Sa | Use of compounds for increasing spermatozoa motility |
| BR0312650A (pt) | 2002-07-10 | 2005-05-03 | Applied Research Systems | Derivados de benzeno fundido azolidinona-vinila |
| US20040092561A1 (en) | 2002-11-07 | 2004-05-13 | Thomas Ruckle | Azolidinone-vinyl fused -benzene derivatives |
| JP4646626B2 (ja) * | 2002-08-16 | 2011-03-09 | アストラゼネカ アクチボラグ | ホスホイノシチド３−キナーゼβの阻害 |
| WO2004017950A2 (en) | 2002-08-22 | 2004-03-04 | Piramed Limited | Phosphadidylinositol 3,5-biphosphate inhibitors as anti-viral agents |
| US7605155B2 (en) | 2002-09-04 | 2009-10-20 | Schering Corporation | Substituted pyrazolo[1,5-a]pyrimidines as protein kinase inhibitors |
| US7601724B2 (en) | 2002-09-04 | 2009-10-13 | Schering Corporation | Substituted pyrazolo[1,5-a]pyrimidines as protein kinase inhibitors |
| WO2004072029A2 (en) | 2003-02-06 | 2004-08-26 | Vertex Pharmaceuticals Incorporated | Pyrazolopyridazines useful as inhibitors of protein kinases |
| GB0305152D0 (en) * | 2003-03-06 | 2003-04-09 | Novartis Ag | Organic compounds |
| BRPI0409063A (pt) * | 2003-04-03 | 2006-03-28 | Semafore Pharmaceuticals Inc | pró medicamentos de inibidor de pi-3 cinase |
| ATE446752T1 (de) | 2003-04-24 | 2009-11-15 | Merck & Co Inc | Hemmer der akt aktivität |
| EP1651958B1 (en) * | 2003-07-30 | 2010-06-16 | Roche Diagnostics GmbH | Novel chemiluminescent compounds and their use |
| AR045731A1 (es) | 2003-08-06 | 2005-11-09 | Vertex Pharma | Compuestos de aminotriazol utiles como inhibidores de quinasas de proteinas |
| US7501427B2 (en) | 2003-08-14 | 2009-03-10 | Array Biopharma, Inc. | Quinazoline analogs as receptor tyrosine kinase inhibitors |
| US20050043239A1 (en) | 2003-08-14 | 2005-02-24 | Jason Douangpanya | Methods of inhibiting immune responses stimulated by an endogenous factor |
| US20060058311A1 (en) | 2004-08-14 | 2006-03-16 | Boehringer Ingelheim International Gmbh | Combinations for the treatment of diseases involving cell proliferation |
| EP1796467A4 (en) | 2004-09-24 | 2009-07-01 | Janssen Pharmaceutica Nv | INHIBITORS IMIDAZO {4,5-B} PYRAZINONE PROTEIN KINASES |
| GB0423653D0 (en) | 2004-10-25 | 2004-11-24 | Piramed Ltd | Pharmaceutical compounds |
| MY179032A (en) | 2004-10-25 | 2020-10-26 | Cancer Research Tech Ltd | Ortho-condensed pyridine and pyrimidine derivatives (e.g.purines) as protein kinase inhibitors |
| WO2008007113A2 (en) | 2006-07-14 | 2008-01-17 | Astex Therapeutics Limited | Pharmaceutical combinations |
| FR2882751B1 (fr) | 2005-03-04 | 2007-09-14 | Aventis Pharma Sa | Hydrazinocarbonyl-thieno[2,3-c]pyrazoles, procede de preparation, compositions les contenant et utilisation |
| AU2006269504A1 (en) | 2005-07-08 | 2007-01-18 | Merck Sharp & Dohme Corp. | Inhibitors of checkpoint kinases |
| EP1919924A2 (en) | 2005-08-16 | 2008-05-14 | Irm, Llc | Compounds and compositions as protein kinase inhibitors |
| DK1937671T3 (da) | 2005-09-06 | 2010-04-26 | Glaxosmithkline Llc | Benzimidazolthiophenforbindelser som PLK-inhibitorer |
| KR20140105621A (ko) | 2005-10-07 | 2014-09-01 | 엑셀리시스, 인코포레이티드 | ＰＩ３Ｋα의 피리도피리미디논 억제제 |
| GB0520657D0 (en) | 2005-10-11 | 2005-11-16 | Ludwig Inst Cancer Res | Pharmaceutical compounds |
| JP2009512706A (ja) | 2005-10-21 | 2009-03-26 | メルク エンド カムパニー インコーポレーテッド | チロシンキナーゼインヒビター |
| EA200801716A1 (ru) | 2006-01-18 | 2009-04-28 | Амген Инк. | Тиазольные соединения и их применение |
| US20090233950A1 (en) | 2006-03-02 | 2009-09-17 | Frederic Henri Jung | Quinazoline derivatives |
| WO2007117995A2 (en) | 2006-03-30 | 2007-10-18 | Takeda San Diego, Inc. | Kinase inhibitors |
| AU2007347115A1 (en) * | 2006-04-04 | 2008-10-23 | The Regents Of The University Of California | PI3 kinase antagonists |
| BRPI0710874A2 (pt) | 2006-04-26 | 2012-02-14 | Hoffmann La Roche | compostos de tienopirimidina, processos de produção dos referidos compostos, composições farmacêuticas contendo os mesmos, kit, produto, e usos dos compostos |
| KR101402474B1 (ko) | 2006-04-26 | 2014-06-19 | 제넨테크, 인크. | 포스포이노시티드 3-키나제 억제제 화합물 및 이를 포함하는 약학적 조성물 |
| EP2025347A4 (en) | 2006-05-15 | 2010-08-11 | Takeda Pharmaceutical | PROPHYLACTIC AND THERAPEUTIC AGENTS AGAINST CANCER |
| GB0610243D0 (en) | 2006-05-23 | 2006-07-05 | Novartis Ag | Organic compounds |
| ES2393410T3 (es) | 2006-08-09 | 2012-12-21 | Bristol-Myers Squibb Company | Pirrolotriazinas inhibidoras de quinasas |
| CN101563340A (zh) | 2006-09-14 | 2009-10-21 | 阿斯利康(瑞典)有限公司 | 用作pi3k和mtor抑制剂用于治疗增殖性疾病的2-苯并咪唑基-6-吗啉代-4-哌啶-4-基嘧啶衍生物 |
| TWI499420B (zh) | 2006-12-07 | 2015-09-11 | Hoffmann La Roche | 肌醇磷脂３-激酶抑制劑化合物及使用方法 |
| KR101507182B1 (ko) | 2006-12-07 | 2015-03-30 | 제넨테크, 인크. | 포스포이노시타이드 3-키나제 억제제 화합물 및 그의 사용 방법 |
| HRP20140147T1 (hr) * | 2007-03-23 | 2014-03-28 | Amgen Inc. | 3-supstituirani derivati hinolina ili hinoksalina i njihova uporaba kao inhibitora fosfatidilinozitol 3-kinaze (pi3k) |
| EP2150255A4 (en) | 2007-05-10 | 2011-10-05 | Glaxosmithkline Llc | CHINOXALINE DERIVATIVES AS P13 KINASE INHIBITORS |
| US20090263397A1 (en) | 2007-07-06 | 2009-10-22 | Buck Elizabeth A | Combination anti-cancer therapy |
| EP2231641B1 (en) * | 2007-12-21 | 2016-06-01 | UCB Biopharma SPRL | Quinoxaline and quinoline derivatives as kinase inhibitors |
| DK2240451T3 (da) * | 2008-01-04 | 2017-11-20 | Intellikine Llc | Isoquinolinonderivater substitueret med en purin, der er anvendelig som pi3k-inhibitorer |
| WO2009105712A1 (en) | 2008-02-22 | 2009-08-27 | Irm Llc | Heterocyclic compounds and compositions as c-kit and pdgfr kinase inhibitors |
| CA2716755A1 (en) | 2008-02-29 | 2009-09-03 | Peter C. Chua | Protein kinase modulators |
| WO2009111547A1 (en) | 2008-03-04 | 2009-09-11 | Wyeth | 7h-pyrrolo[2,3-h]quinazoline compounds, their use as mtor kinase and pi3 kinase inhibitors, and their synthesis |
| WO2009109867A2 (en) | 2008-03-04 | 2009-09-11 | Natco Pharma Limited | Crystal form of phenylamino pyrimidine derivatives |
| CN102015719A (zh) | 2008-03-06 | 2011-04-13 | 百时美施贵宝公司 | 吡咯并三嗪激酶抑制剂 |
| UY31700A (es) | 2008-03-13 | 2009-11-10 | Boehringer Ingelheim Int | Tiazolil-dihidro-indazoles |
| US8993580B2 (en) | 2008-03-14 | 2015-03-31 | Intellikine Llc | Benzothiazole kinase inhibitors and methods of use |
| US8637542B2 (en) | 2008-03-14 | 2014-01-28 | Intellikine, Inc. | Kinase inhibitors and methods of use |
| US8268834B2 (en) | 2008-03-19 | 2012-09-18 | Novartis Ag | Pyrazine derivatives that inhibit phosphatidylinositol 3-kinase enzyme |
| EP2276763A1 (en) | 2008-03-19 | 2011-01-26 | OSI Pharmaceuticals, Inc. | Mtor inhibitor salt forms |
| MX2010010272A (es) | 2008-03-19 | 2011-05-25 | Chembridge Corp | Nuevos inhibidores de tirosina quinasa. |
| US20110053907A1 (en) | 2008-03-27 | 2011-03-03 | Auckland Uniservices Limited | Substituted pyrimidines and triazines and their use in cancer therapy |
| PL2276767T3 (pl) | 2008-03-31 | 2014-09-30 | Genentech Inc | Związki benzopiranowe i benzoksepinowe będące inhibitorami pi3k oraz metody ich stosowania |
| US20090258907A1 (en) | 2008-04-09 | 2009-10-15 | Abbott Laboratories | Compounds useful as inhibitors of rock kinases |
| MX2010011370A (es) | 2008-04-16 | 2010-12-15 | Vertex Pharma | Inhibidores de fosfatidilinositol 3-cinasa. |
| JP2011518171A (ja) | 2008-04-16 | 2011-06-23 | 武田薬品工業株式会社 | ５−（３−（エチルスルホニル）フェニル）−３，８−ジメチル−ｎ−（１−メチルピペリドン−４−イル）−９ｈ−ピリド［２，３−ｂ］インドール−７−カルボキサミドの多形およびその使用方法 |
| AP2012006294A0 (en) | 2009-11-05 | 2012-06-30 | Rhizen Pharmaceuticals Sa | Novel kinase modulators. |
| DK2533637T3 (da) * | 2010-02-12 | 2014-05-19 | N30 Pharmaceuticals Inc | Chromoninhibitorer af S-nitrosoglutathionreduktase |
| DK2705029T3 (en) | 2011-05-04 | 2019-02-18 | Rhizen Pharmaceuticals S A | Hitherto UNKNOWN RELATIONS AS MODULATORS OF PROTEIN KINASES |
| PL2844647T3 (pl) | 2012-05-04 | 2021-01-25 | Rhizen Pharmaceuticals S.A. | Nowy sposób wytwarzania czystych optycznie i opcjonalnie podstawionych pochodnych 2-(1-hydroksyalkilo)-chromen-4-onu i ich zastosowanie do wytwarzania środków farmaceutycznych |
| US9150570B2 (en) | 2012-05-31 | 2015-10-06 | Plexxikon Inc. | Synthesis of heterocyclic compounds |
| MX357043B (es) | 2012-07-04 | 2018-06-25 | Rhizen Pharmaceuticals Sa | Inhibidores selectivos de pi3k delta. |
| US9737521B2 (en) | 2012-11-08 | 2017-08-22 | Rhizen Pharmaceuticals Sa | Pharmaceutical compositions containing a PDE4 inhibitor and a PI3 delta or dual PI3 delta-gamma kinase inhibitor |
-
2010
- 2010-11-03 AP AP2012006294A patent/AP2012006294A0/xx unknown
- 2010-11-03 LT LTEP10803619.5T patent/LT2496567T/lt unknown
- 2010-11-03 EA EA201790267A patent/EA036876B1/ru unknown
- 2010-11-03 EP EP16159544.2A patent/EP3050876A3/en not_active Withdrawn
- 2010-11-03 AU AU2010316780A patent/AU2010316780B2/en active Active
- 2010-11-03 JP JP2012537454A patent/JP5889795B2/ja active Active
- 2010-11-03 CA CA2779574A patent/CA2779574C/en active Active
- 2010-11-03 RS RS20171017A patent/RS56432B1/sr unknown
- 2010-11-03 KR KR1020187001585A patent/KR102012398B1/ko not_active Expired - Fee Related
- 2010-11-03 HR HRP20171537TT patent/HRP20171537T1/hr unknown
- 2010-11-03 CN CN201080060611.5A patent/CN102812013B/zh active Active
- 2010-11-03 WO PCT/IB2010/002804 patent/WO2011055215A2/en not_active Ceased
- 2010-11-03 SM SM20170468T patent/SMT201700468T1/it unknown
- 2010-11-03 PL PL10803619T patent/PL2496567T3/pl unknown
- 2010-11-03 US US12/938,609 patent/US10442783B2/en not_active Expired - Fee Related
- 2010-11-03 EP EP10803619.5A patent/EP2496567B1/en active Active
- 2010-11-03 CN CN201610136199.XA patent/CN105801550B/zh not_active Expired - Fee Related
- 2010-11-03 ES ES10803619.5T patent/ES2651682T3/es active Active
- 2010-11-03 KR KR1020127014647A patent/KR101821768B1/ko active Active
- 2010-11-03 PH PH1/2012/500901A patent/PH12012500901A1/en unknown
- 2010-11-03 EA EA201290209A patent/EA027123B1/ru unknown
- 2010-11-03 HU HUE10803619A patent/HUE035059T2/hu unknown
- 2010-11-03 BR BR112012010640A patent/BR112012010640A2/pt not_active Application Discontinuation
- 2010-11-03 NZ NZ599830A patent/NZ599830A/en not_active IP Right Cessation
- 2010-11-03 MX MX2012005301A patent/MX352661B/es active IP Right Grant
- 2010-11-03 MY MYPI2012002000A patent/MY173795A/en unknown
- 2010-11-03 PT PT108036195T patent/PT2496567T/pt unknown
- 2010-11-03 SG SG10201500895XA patent/SG10201500895XA/en unknown
- 2010-11-03 EP EP18196806.6A patent/EP3444242A3/en not_active Withdrawn
- 2010-11-03 DK DK10803619.5T patent/DK2496567T3/en active
- 2010-11-03 CA CA3022722A patent/CA3022722A1/en not_active Abandoned
- 2010-11-03 SI SI201031561T patent/SI2496567T1/en unknown
-
2011
- 2011-11-09 US US13/292,746 patent/US8642607B2/en active Active
-
2012
- 2012-05-03 IL IL219585A patent/IL219585A/en active IP Right Grant
- 2012-05-25 ZA ZA2012/03849A patent/ZA201203849B/en unknown
- 2012-06-04 CO CO12093609A patent/CO6551721A2/es active IP Right Grant
-
2013
- 2013-11-26 US US14/090,517 patent/US9018375B2/en active Active
-
2015
- 2015-03-09 US US14/642,423 patent/US9421209B2/en not_active Expired - Fee Related
- 2015-08-17 PH PH12015501806A patent/PH12015501806B1/en unknown
- 2015-10-16 AU AU2015243070A patent/AU2015243070B2/en not_active Ceased
-
2016
- 2016-02-17 JP JP2016027735A patent/JP6385966B2/ja not_active Expired - Fee Related
- 2016-07-13 US US15/208,984 patent/US10538501B2/en not_active Expired - Fee Related
-
2017
- 2017-10-12 CY CY20171101071T patent/CY1119766T1/el unknown
-
2018
- 2018-04-18 JP JP2018079763A patent/JP2018111727A/ja active Pending
-
2019
- 2019-08-30 US US16/557,553 patent/US11858907B2/en active Active
-
2023
- 2023-11-13 US US18/508,085 patent/US20240360095A1/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2013510133A5 (OSRAM) | ||
| SI2496567T1 (en) | Novel benzopyran kinase modulators | |
| JP6461118B2 (ja) | ブロモドメイン阻害剤としての新規の置換された二環式化合物 | |
| Gillespie et al. | Antagonists of the human A2A adenosine receptor. 4. Design, synthesis, and preclinical evaluation of 7-aryltriazolo [4, 5-d] pyrimidines | |
| JP5925394B2 (ja) | 抗レトロウイルス剤としての（ヘテロ）アリールアセトアミド誘導体 | |
| CA3077499C (en) | P38 kinase inhibitors reduce dux4 and downstream gene expression for the treatment of fshd | |
| JP2017505808A5 (OSRAM) | ||
| CN109963854A (zh) | 杂芳基并[4,3-c]嘧啶-5-胺类衍生物、其制备方法及其在医药上的应用 | |
| WO2015092634A1 (en) | 1,2,3,4-tetrahydroisoquinoline compounds and compositions as selective estrogen receptor antagonists and degraders | |
| HRP20171610T1 (hr) | Selektivni inhibitori pi3k delta | |
| PH12015501058B1 (en) | Pyrimidine-2,4-diamine derivatives for treatment of cancer | |
| JP2016525078A5 (OSRAM) | ||
| JP2013516393A5 (OSRAM) | ||
| TW200536849A (en) | Substituted heterocycles and the uses thereof | |
| TW200811176A (en) | Dihydropyrazolopyrimidinone derivatives | |
| JP2017537946A (ja) | ブロモドメイン阻害剤としての置換複素環 | |
| RU2019101002A (ru) | Производные n-(замещенный фенил)-сульфонамида в качестве ингибиторов киназы | |
| EA029093B1 (ru) | Соединения и композиции в качестве ингибиторов mek | |
| CN117624194A (zh) | Kras g12d抑制剂及其在医药上的应用 | |
| JP2021500340A5 (OSRAM) | ||
| ES2837018T3 (es) | Ligandos del receptor D3 de dopamina de 6,7,8,9-tetrahidro-5H-pirido[2,3-d]azepina | |
| CN111511745A (zh) | 吡唑并[1,5-a][1,3,5]三嗪-2-胺类衍生物、其制备方法及其在医药上的应用 | |
| JP2025513483A (ja) | ピラゾール置換シクロペンチルエステル誘導体及びその用途 | |
| JP2013511526A5 (OSRAM) | ||
| JP2022519764A (ja) | 二環式スルホンアミド |