JP2013510133A5 - - Google Patents
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- 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
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- 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
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Families Citing this family (73)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2725014C (en) | 2008-05-30 | 2014-06-17 | Amgen Inc. | Inhibitors of pi3 kinase |
| KR101763656B1 (ko) | 2009-06-29 | 2017-08-01 | 인사이트 홀딩스 코포레이션 | Ｐｉ3ｋ 저해물질로서의 피리미디논 |
| NZ599830A (en) * | 2009-11-05 | 2014-08-29 | Rhizen Pharmaceuticals Sa | Novel kinase modulators |
| KR102263079B1 (ko) * | 2009-11-05 | 2021-06-10 | 리젠 파마슈티컬스 소시에떼 아노님 | 신규한 벤조피란 키나제 조절제 |
| US8759359B2 (en) | 2009-12-18 | 2014-06-24 | Incyte Corporation | Substituted heteroaryl fused derivatives as PI3K inhibitors |
| EP2558463A1 (en) | 2010-04-14 | 2013-02-20 | Incyte Corporation | Fused derivatives as i3 inhibitors |
| WO2011163195A1 (en) | 2010-06-21 | 2011-12-29 | Incyte Corporation | Fused pyrrole derivatives as pi3k inhibitors |
| EP3660016A1 (en) | 2010-12-20 | 2020-06-03 | 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 |
| WO2012135009A1 (en) | 2011-03-25 | 2012-10-04 | Incyte Corporation | Pyrimidine-4,6-diamine derivatives as pi3k inhibitors |
| PH12013502240B1 (en) | 2011-05-04 | 2018-06-27 | Rhizen Pharmaceuticals Sa | Novel compounds as modulators of protein kinase |
| JP2014520863A (ja) | 2011-07-13 | 2014-08-25 | ファーマサイクリックス，インク． | Ｂｒｕｔｏｎ型チロシンキナーゼの阻害剤 |
| PT3513793T (pt) | 2011-09-02 | 2021-05-10 | Incyte Holdings Corp | Heterociclilaminas como inibidores de pi3k |
| EP2790705B1 (en) | 2011-12-15 | 2017-12-06 | Novartis AG | Use of inhibitors of the activity or function of 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 |
| 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 |
| WO2013164801A1 (en) * | 2012-05-04 | 2013-11-07 | 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 |
| 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 |
| RS56494B1 (sr) * | 2012-07-04 | 2018-01-31 | Rhizen Pharmaceuticals S A | Selektivni inhibitori pi3k delta |
| WO2014017643A1 (ja) * | 2012-07-27 | 2014-01-30 | 佐藤製薬株式会社 | ジフルオロメチレン化合物 |
| 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 |
| WO2014072937A1 (en) * | 2012-11-08 | 2014-05-15 | Rhizen Pharmaceuticals Sa | Pharmaceutical compositions containing a pde4 inhibitor and a pi3 delta or dual pi3 delta-gamma kinase inhibitor |
| SI3004106T1 (en) | 2013-06-07 | 2018-03-30 | Rhizen Pharmaceuticals S.A. | Dual selective PI3 delta and gamma inhibitors |
| CN105431437B (zh) | 2013-07-02 | 2020-03-10 | 理森制药股份公司 | PI3K蛋白激酶抑制剂，特别是δ抑制剂和/或γ抑制剂 |
| AR098776A1 (es) * | 2013-12-18 | 2016-06-15 | Chiesi Farm Spa | Derivados del isocromeno como inhibidores de las fosfoinositido-3 quinasas |
| KR20160100408A (ko) * | 2014-01-06 | 2016-08-23 | 리젠 파마슈티컬스 소시에떼 아노님 | 신규한 글루타미나제 저해제 |
| WO2015191677A1 (en) | 2014-06-11 | 2015-12-17 | Incyte Corporation | Bicyclic heteroarylaminoalkyl phenyl derivatives as pi3k inhibitors |
| AP2017009670A0 (en) * | 2014-06-27 | 2017-01-31 | Rhizen Pharmaceuticals Sa | Substituted chromene derivatives as selective dual 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 |
| HK1232227A1 (zh) | 2014-07-04 | 2018-01-05 | Lupin Limited | 作为pi3k抑制剂的喹嗪酮衍生物 |
| ES2802202T3 (es) | 2014-09-03 | 2021-01-15 | Rhizen Pharmaceuticals S A | Método de tratamiento y composiciones que comprenden un inhibidor dual de la quinasa PI3K delta-gama y un corticoesteroide |
| US9950194B2 (en) | 2014-09-09 | 2018-04-24 | Mevion Medical Systems, Inc. | Patient positioning system |
| SG10201907576SA (en) | 2015-02-27 | 2019-09-27 | Incyte Corp | Salts of pi3k inhibitor and processes for their preparation |
| 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 |
| US9732097B2 (en) | 2015-05-11 | 2017-08-15 | Incyte Corporation | Process for the synthesis of a phosphoinositide 3-kinase inhibitor |
| US9988401B2 (en) | 2015-05-11 | 2018-06-05 | Incyte Corporation | Crystalline forms of a PI3K inhibitor |
| EP3325462A4 (en) * | 2015-07-23 | 2019-06-19 | Pharmakea, Inc. | INHIBITORS OF LYSYL OXIDASE-LIKE 2 AND USES OF SAID INHIBITORS |
| CA3013917A1 (en) | 2016-02-09 | 2017-08-17 | Pharmakea, Inc. | Quinolinone lysyl oxidase-like 2 inhibitors and uses thereof |
| GB201602527D0 (en) * | 2016-02-12 | 2016-03-30 | Glaxosmithkline Ip Dev Ltd | Chemical compounds |
| WO2017178844A1 (en) | 2016-04-15 | 2017-10-19 | Cancer Research Technology Limited | Heterocyclic compounds as ret kinase inhibitors |
| SI3442535T1 (sl) | 2016-04-15 | 2023-01-31 | Cancer Research Technology Limited | Heterociklične spojine kot zaviralci RET-kinaze |
| EP3463318A4 (en) | 2016-05-27 | 2020-01-01 | TG Therapeutics Inc. | COMBINATION OF ANTI-CD20-ANTIBODIES, P13-KINASE-DELTA-SELECTIVE INHIBITOR AND BTK-INHIBITOR FOR THE TREATMENT OF PROLIFERATIVE B-CELL DISORDERS |
| WO2018049263A1 (en) | 2016-09-09 | 2018-03-15 | 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 |
| WO2018136661A1 (en) | 2017-01-18 | 2018-07-26 | Andrews Steven W | SUBSTITUTED PYRAZOLO[1,5-a]PYRAZINE COMPOUNDS AS RET KINASE INHIBITORS |
| GB201705971D0 (en) | 2017-04-13 | 2017-05-31 | Cancer Res Tech Ltd | Inhibitor compounds |
| CA3084905A1 (en) * | 2017-12-06 | 2019-06-13 | Rhizen Pharmaceuticals Sa | Composition and method for treating peripheral t-cell lymphoma and cutaneous t-cell lymphoma |
| JP7060694B2 (ja) * | 2018-01-18 | 2022-04-26 | アレイ バイオファーマ インコーポレイテッド | Ｒｅｔキナーゼ阻害剤としての置換ピロロ［２，３－ｄ］ピリミジン化合物 |
| EP3740490A1 (en) | 2018-01-18 | 2020-11-25 | Array Biopharma, Inc. | Substituted pyrazolo[3,4-d]pyrimidine compounds as ret kinase inhibitors |
| US11472802B2 (en) | 2018-01-18 | 2022-10-18 | Array Biopharma Inc. | Substituted pyrazolyl[4,3-c]pyridine compounds as RET kinase inhibitors |
| SG11202011680YA (en) | 2018-06-01 | 2020-12-30 | Incyte Corp | Dosing regimen for the treatment of pi3k related disorders |
| JP2021535907A (ja) * | 2018-08-21 | 2021-12-23 | 南京明徳新薬研発有限公司 | ピラゾロピリミジン誘導体及びそのｐｉ３ｋ抑制剤とする適用 |
| CN112996794A (zh) | 2018-09-10 | 2021-06-18 | 阿雷生物药品公司 | 作为ret激酶抑制剂的稠合杂环化合物 |
| WO2020200918A1 (en) | 2019-04-04 | 2020-10-08 | Chiesi Farmaceutici S.P.A. | Isochromene derivatives as phosphoinositide 3-kinases inhibitors |
| 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 |
| 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 |
| 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 |
| 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 |
| US11965032B1 (en) | 2022-06-01 | 2024-04-23 | Tg Therapeutics, Inc. | Anti-CD20 antibody compositions |
| US11807689B1 (en) | 2022-06-01 | 2023-11-07 | Tg Therapeutics, Inc. | Anti-CD20 antibody compositions |
| US11884740B1 (en) | 2022-06-01 | 2024-01-30 | Tg Therapeutics, Inc. | Anti-CD20 antibody compositions |
| US11814439B1 (en) | 2022-06-01 | 2023-11-14 | Tg Therapeutics, Inc. | Anti-CD20 antibody compositions |
| JP2026510901A (ja) * | 2023-03-15 | 2026-04-10 | エーエヌ２ セラピューティックス，インコーポレイテッド | 化学化合物 |
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 |
| AU610083B2 (en) | 1986-08-18 | 1991-05-16 | Clinical Technologies Associates, Inc. | Delivery systems for pharmacological agents |
| 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 |
| WO1993021259A1 (en) | 1992-04-14 | 1993-10-28 | Cornell Research Foundation Inc. | Dendritic based macromolecules and method of production |
| 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 |
| ES2153031T4 (es) | 1995-04-20 | 2001-05-16 | Pfizer | Derivados del acido arilsulfonil hidroxamico como inhibidores de mmp y 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 |
| KR20000067904A (ko) | 1996-07-18 | 2000-11-25 | 디. 제이. 우드, 스피겔 알렌 제이 | 매트릭스 메탈로프로테아제의 포스피네이트계 억제제 |
| KR20000068248A (ko) | 1996-08-23 | 2000-11-25 | 디. 제이. 우드, 스피겔 알렌 제이 | 아릴설포닐아미노 하이드록삼산 유도체 |
| IT1289154B1 (it) * | 1997-01-03 | 1998-09-29 | Chiesi Farma Spa | Derivati di isoflavone loro preparazione e loro impiego terapeutico |
| JP3338064B2 (ja) | 1997-01-06 | 2002-10-28 | ファイザー・インク | 環状スルホン誘導体 |
| NZ336840A (en) | 1997-02-03 | 2001-01-26 | Pfizer Prod Inc | Arylsulfonylamino hydroxamic acid derivatives useful in the treatment of tumor necrosis factor and matrix metalloproteinase mediated diseases |
| JP2000507975A (ja) | 1997-02-07 | 2000-06-27 | ファイザー・インク | Ｎ−ヒドロキシ−β−スルホニルプロピオンアミド誘導体類及びそれらのマトリックスメタロプロテイナーゼ阻害薬としての使用 |
| EP0960098A1 (en) | 1997-02-11 | 1999-12-01 | Pfizer Inc. | Arylsulfonyl hydroxamic acid derivatives |
| US6605599B1 (en) | 1997-07-08 | 2003-08-12 | Bristol-Myers Squibb Company | Epothilone derivatives |
| CA2299355C (en) | 1997-08-08 | 2005-09-27 | Pfizer Products Inc. | Aryloxyarylsulfonylamino hydroxamic acid derivatives |
| 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 |
| EP1004578B1 (en) | 1998-11-05 | 2004-02-25 | Pfizer Products Inc. | 5-oxo-pyrrolidine-2-carboxylic acid hydroxamide derivatives |
| CZ301498B6 (cs) | 1999-02-22 | 2010-03-24 | Gesellschaft Fuer Biotechnologische Forschung Mbh (Gbf) | C-21 modifikované epothilony |
| 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 |
| GEP20084317B (en) | 2000-04-25 | 2008-02-25 | Icos Corp | Inhibitors of human phosphatidyl-inositol 3-kinase delta |
| US6608053B2 (en) | 2000-04-27 | 2003-08-19 | Yamanouchi Pharmaceutical Co., Ltd. | Fused heteroaryl derivatives |
| US6403588B1 (en) | 2000-04-27 | 2002-06-11 | Yamanouchi Pharmaceutical Co., Ltd. | Imidazopyridine 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 |
| CA2454976C (en) | 2001-07-26 | 2011-05-10 | Santen Pharmaceutical Co., Ltd. | Therapeutic agent for glaucoma comprising compound having pi3 kinase inhibitory action as active ingredient |
| 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 |
| WO2003035618A2 (en) | 2001-10-24 | 2003-05-01 | Iconix Pharmaceuticals, Inc. | Modulators of phosphoinositide 3-kinase |
| JP2005509645A (ja) | 2001-10-30 | 2005-04-14 | ファルマシア・コーポレーション | 炎症処置用のヘテロ芳香族カルボキサミド誘導体 |
| NZ536190A (en) | 2002-04-17 | 2007-08-31 | Cytokinetics Inc | Compounds for treating cellular proliferative diseases by modulating the activity of the mitotic kinesin KSP |
| US20040092561A1 (en) | 2002-11-07 | 2004-05-13 | Thomas Ruckle | Azolidinone-vinyl fused -benzene derivatives |
| AU2003255529B2 (en) | 2002-07-10 | 2008-11-20 | Laboratoires Serono Sa | Use of compounds for increasing spermatozoa motility |
| JP4782564B2 (ja) | 2002-07-10 | 2011-09-28 | メルク セローノ ソシエテ アノニム | アゾリジノン−ビニル縮合−ベンゼン誘導体 |
| US7598377B2 (en) * | 2002-08-16 | 2009-10-06 | Astrazeneca Ab | Inhibition of phosphoinositide 3-kinase β |
| AU2003255845A1 (en) | 2002-08-22 | 2004-03-11 | Piramed Limited | Phosphadidylinositol 3,5-biphosphate inhibitors as anti-viral agents |
| US7601724B2 (en) | 2002-09-04 | 2009-10-13 | Schering Corporation | Substituted pyrazolo[1,5-a]pyrimidines as protein kinase inhibitors |
| US7605155B2 (en) | 2002-09-04 | 2009-10-20 | Schering Corporation | Substituted pyrazolo[1,5-a]pyrimidines as protein kinase inhibitors |
| US7601718B2 (en) | 2003-02-06 | 2009-10-13 | Vertex Pharmaceuticals Incorporated | Compositions useful as inhibitors of protein kinases |
| GB0305152D0 (en) * | 2003-03-06 | 2003-04-09 | Novartis Ag | Organic compounds |
| AU2004228668B2 (en) * | 2003-04-03 | 2011-10-27 | Park Funding, Llc | PI-3 kinase inhibitor prodrugs |
| US7414055B2 (en) | 2003-04-24 | 2008-08-19 | Merck & Co., Inc. | Inhibitors of Akt activity |
| EP1651958B1 (en) * | 2003-07-30 | 2010-06-16 | Roche Diagnostics GmbH | Novel chemiluminescent compounds and their use |
| WO2005013982A1 (en) | 2003-08-06 | 2005-02-17 | Vertex Pharmaceuticals Incorporated | Aminotriazole compounds useful as inhibitors of protein kinases |
| WO2005016348A1 (en) | 2003-08-14 | 2005-02-24 | Icos Corporation | Method of inhibiting immune responses stimulated by an endogenous factor |
| US7501427B2 (en) | 2003-08-14 | 2009-03-10 | Array Biopharma, Inc. | Quinazoline analogs as receptor tyrosine kinase inhibitors |
| US20060058311A1 (en) | 2004-08-14 | 2006-03-16 | Boehringer Ingelheim International Gmbh | Combinations for the treatment of diseases involving cell proliferation |
| AU2005289644A1 (en) | 2004-09-24 | 2006-04-06 | Janssen Pharmaceutica, N.V. | Imidazo{4,5-b}pyrazinone inhibitors of 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 |
| US20090258852A1 (en) | 2005-07-08 | 2009-10-15 | Arrington Kenneth L | Inhibitors of Checkpoint Kinases |
| US7589101B2 (en) | 2005-08-16 | 2009-09-15 | Irm Llc | Compounds and compositions as protein kinase inhibitors |
| EA014111B1 (ru) | 2005-09-06 | 2010-10-29 | Смитклайн Бичем Корпорейшн | Бензимидазолтиофеновые соединения в качестве ингибиторов polo-подобных киназ (plk) |
| EA016945B1 (ru) | 2005-10-07 | 2012-08-30 | Экселиксис, Инк. | ПИРИДОПИРИМИДИНОНОВЫЕ ИНГИБИТОРЫ PI3Kα |
| GB0520657D0 (en) | 2005-10-11 | 2005-11-16 | Ludwig Inst Cancer Res | Pharmaceutical compounds |
| WO2007050380A2 (en) | 2005-10-21 | 2007-05-03 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| WO2007084391A2 (en) | 2006-01-18 | 2007-07-26 | Amgen Inc. | Thiazole compounds as protein kinase b ( pkb) inhibitors |
| EP1994023A1 (en) | 2006-03-02 | 2008-11-26 | AstraZeneca AB | Quinazoline derivatives |
| JP2009532375A (ja) | 2006-03-30 | 2009-09-10 | タケダ サン ディエゴ インコーポレイテッド | キナーゼ阻害剤 |
| WO2007114926A2 (en) * | 2006-04-04 | 2007-10-11 | The Regents Of The University Of California | Kinase antagonists |
| TW200801012A (en) | 2006-04-26 | 2008-01-01 | Piramed Ltd | Phosphoinositide 3-kinase inhibitor compounds and methods of use |
| WO2007129161A2 (en) | 2006-04-26 | 2007-11-15 | F. Hoffmann-La Roche Ag | Thieno [3, 2-d] pyrimidine derivative useful as pi3k inhibitor |
| JPWO2007132867A1 (ja) | 2006-05-15 | 2009-09-24 | 杉本 芳一 | 癌の予防及び治療剤 |
| GB0610243D0 (en) | 2006-05-23 | 2006-07-05 | Novartis Ag | Organic compounds |
| WO2008021859A1 (en) | 2006-08-09 | 2008-02-21 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
| EP2064203A1 (en) | 2006-09-14 | 2009-06-03 | AstraZeneca AB | 2-benzimidaz0lyl-6-m0rph0lin0-4-piperidin-4-ylpyrimidine derivatives as pi3k and mtor inhibitors for the treatment of proliferative disorders |
| RU2470936C2 (ru) | 2006-12-07 | 2012-12-27 | Дженентек, Инк. | Соединения-ингибиторы фосфоинозитид 3-киназы и способы применения |
| MX2009005950A (es) | 2006-12-07 | 2009-10-12 | Genentech Inc | Compuestos inhibidores de fosfoinositido 3-quinasas y metodos de uso. |
| EP2139882B1 (en) | 2007-03-23 | 2013-12-25 | Amgen Inc. | 3- substituted quinoline or quinoxaline derivatives and their use as phosphatidylinositol 3-kinase (pi3k) inhibitors |
| PE20090288A1 (es) | 2007-05-10 | 2009-04-03 | Smithkline Beecham Corp | Derivados de quinoxalina como inhibidores de la pi3 quinasa |
| EP2173338A1 (en) | 2007-07-06 | 2010-04-14 | OSI Pharmaceuticals, Inc. | Combination anti-cancer therapy |
| EP2231641B1 (en) | 2007-12-21 | 2016-06-01 | UCB Biopharma SPRL | Quinoxaline and quinoline derivatives as kinase inhibitors |
| MX2010007419A (es) * | 2008-01-04 | 2010-11-12 | Intellikine Inc | Ciertas entidades quimicas, composiciones y metodos. |
| EA018551B1 (ru) | 2008-02-22 | 2013-08-30 | Айрм Ллк | ГЕТЕРОЦИКЛИЧЕСКИЕ СОЕДИНЕНИЯ И СОДЕРЖАЩИЕ ИХ КОМПОЗИЦИИ В КАЧЕСТВЕ ИНГИБИТОРОВ КИНАЗ c-KIT И PDGFR |
| JP2011515337A (ja) | 2008-02-29 | 2011-05-19 | サイレーン ファーマシューティカルズ， インコーポレイテッド | プロテインキナーゼモジュレーター |
| AP2651A (en) | 2008-03-04 | 2013-04-25 | Natco Pharma Ltd | Crystal form of phenylamino pyrimidine derivatives |
| US20090227575A1 (en) | 2008-03-04 | 2009-09-10 | Wyeth | 7H-PYRROLO[2,3-H]QUINAZOLINE COMPOUNDS, THEIR USE AS mTOR KINASE AND PI3 KINASE INHIBITORS, AND THEIR SYNTHESIS |
| JP2011513419A (ja) | 2008-03-06 | 2011-04-28 | ブリストル−マイヤーズ スクイブ カンパニー | ピロロトリアジンキナーゼ阻害剤 |
| 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 |
| EP2252293B1 (en) | 2008-03-14 | 2018-06-27 | Intellikine, LLC | 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. |
| JP2011515462A (ja) | 2008-03-27 | 2011-05-19 | アウククランド ウニセルビセス リミテッド | 置換されたピリミジン、及びトリアジン、並びに癌療法におけるこれらの使用 |
| MX2010010659A (es) | 2008-03-31 | 2010-10-26 | Genentech Inc | Compuestos de benzopirano y benzoxepina, inhibidores de fosfoinoinositida 3-cinasas y metodos para utilizarlos. |
| WO2009126635A1 (en) | 2008-04-09 | 2009-10-15 | Abbott Laboratories | 2-amino-benzothiazole derivates 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 |
| NZ599830A (en) | 2009-11-05 | 2014-08-29 | Rhizen Pharmaceuticals Sa | Novel kinase modulators |
| EP2533637B1 (en) * | 2010-02-12 | 2014-03-26 | N30 Pharmaceuticals, Inc. | Chromone inhibitors of s-nitrosoglutathione reductase |
| PH12013502240B1 (en) | 2011-05-04 | 2018-06-27 | Rhizen Pharmaceuticals Sa | Novel compounds as modulators of protein kinase |
| WO2013164801A1 (en) | 2012-05-04 | 2013-11-07 | 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 |
| US9150570B2 (en) | 2012-05-31 | 2015-10-06 | Plexxikon Inc. | Synthesis of heterocyclic compounds |
| RS56494B1 (sr) | 2012-07-04 | 2018-01-31 | Rhizen Pharmaceuticals S A | Selektivni inhibitori pi3k delta |
| WO2014072937A1 (en) | 2012-11-08 | 2014-05-15 | Rhizen Pharmaceuticals Sa | Pharmaceutical compositions containing a pde4 inhibitor and a pi3 delta or dual pi3 delta-gamma kinase inhibitor |
-
2010
- 2010-11-03 NZ NZ599830A patent/NZ599830A/en not_active IP Right Cessation
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