JP2016510035A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2016510035A5 JP2016510035A5 JP2015560346A JP2015560346A JP2016510035A5 JP 2016510035 A5 JP2016510035 A5 JP 2016510035A5 JP 2015560346 A JP2015560346 A JP 2015560346A JP 2015560346 A JP2015560346 A JP 2015560346A JP 2016510035 A5 JP2016510035 A5 JP 2016510035A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- ethyl
- pyrazolo
- chloro
- amino
- 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 50
- 239000003814 drug Substances 0.000 claims 27
- -1 thio Chemical group 0.000 claims 22
- 150000001875 compounds Chemical class 0.000 claims 17
- 125000005843 halogen group Chemical group 0.000 claims 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 15
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 12
- 229910052799 carbon Inorganic materials 0.000 claims 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 11
- 125000006601 (C1-C3) alkylcarbamyl group Chemical group 0.000 claims 10
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 8
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 7
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 7
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 5
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 5
- 206010025323 Lymphomas Diseases 0.000 claims 5
- 206010047115 Vasculitis Diseases 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 5
- 125000002947 alkylene group Chemical group 0.000 claims 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 5
- 206010012818 diffuse large B-cell lymphoma Diseases 0.000 claims 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 4
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims 4
- 208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 claims 4
- 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims 3
- CEECNMYKERBUGO-UHFFFAOYSA-N 5-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]-n,n-dimethylpyridine-2-carboxamide Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1=CC=C(C(=O)N(C)C)N=C1 CEECNMYKERBUGO-UHFFFAOYSA-N 0.000 claims 3
- 206010043561 Thrombocytopenic purpura Diseases 0.000 claims 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
- WFJBTQYBCMJYNG-UHFFFAOYSA-N 1-[1-[5-chloro-4-fluoro-2-methoxy-3-(1-propan-2-ylazetidin-3-yl)phenyl]ethyl]-3-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(F)=C1C1CN(C(C)C)C1 WFJBTQYBCMJYNG-UHFFFAOYSA-N 0.000 claims 2
- PJXOQIHPWFBWNB-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-2-(azetidin-3-yl)-6-chloro-3-methoxybenzonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CNC1 PJXOQIHPWFBWNB-UHFFFAOYSA-N 0.000 claims 2
- GKLBWXFAKAOGRL-UHFFFAOYSA-N 4-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]-n,n-dimethylpyridine-2-carboxamide Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1=CC=NC(C(=O)N(C)C)=C1 GKLBWXFAKAOGRL-UHFFFAOYSA-N 0.000 claims 2
- VJJSELYTDOGDNE-UHFFFAOYSA-N 4-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]-n-(2-hydroxyethyl)-n-methylpyridine-2-carboxamide Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1=CC=NC(C(=O)N(C)CCO)=C1 VJJSELYTDOGDNE-UHFFFAOYSA-N 0.000 claims 2
- RYYHOGBWUDOVBW-UHFFFAOYSA-N 5-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-methylphenyl]-n,n-dimethylpyridine-2-carboxamide Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1=CC=C(C(=O)N(C)C)N=C1 RYYHOGBWUDOVBW-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 206010018372 Glomerulonephritis membranous Diseases 0.000 claims 2
- 208000035186 Hemolytic Autoimmune Anemia Diseases 0.000 claims 2
- 241000711549 Hepacivirus C Species 0.000 claims 2
- 208000005777 Lupus Nephritis Diseases 0.000 claims 2
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims 2
- 208000025205 Mantle-Cell Lymphoma Diseases 0.000 claims 2
- 241000721454 Pemphigus Species 0.000 claims 2
- 208000007048 Polymyalgia Rheumatica Diseases 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 2
- 206010043540 Thromboangiitis obliterans Diseases 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims 2
- 201000000448 autoimmune hemolytic anemia Diseases 0.000 claims 2
- 125000002393 azetidinyl group Chemical group 0.000 claims 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 2
- 201000003444 follicular lymphoma Diseases 0.000 claims 2
- 201000009277 hairy cell leukemia Diseases 0.000 claims 2
- 208000015446 immunoglobulin a vasculitis Diseases 0.000 claims 2
- 201000008350 membranous glomerulonephritis Diseases 0.000 claims 2
- 231100000855 membranous nephropathy Toxicity 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 2
- GAKDFKQPUPMQJG-ZGTCLIOFSA-N (2r)-1-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]-2-hydroxypropan-1-one Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(C(=O)[C@@H](C)O)C1 GAKDFKQPUPMQJG-ZGTCLIOFSA-N 0.000 claims 1
- LFGMFYJYCSUPQS-YSSOQSIOSA-N (2r)-2-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]-n,n-dimethylpropanamide Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN([C@H](C)C(=O)N(C)C)C1 LFGMFYJYCSUPQS-YSSOQSIOSA-N 0.000 claims 1
- NNRGDBFNOMUWIU-ARLHGKGLSA-N (2r)-2-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]-n-methylpropanamide Chemical compound C1N([C@H](C)C(=O)NC)CC1C1=C(C)C(Cl)=CC(C(C)N2C3=NC=NC(N)=C3C(C)=N2)=C1OC NNRGDBFNOMUWIU-ARLHGKGLSA-N 0.000 claims 1
- FXHJMVGKCZMISA-YNODCEANSA-N (2r)-2-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]propan-1-ol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN([C@H](C)CO)C1 FXHJMVGKCZMISA-YNODCEANSA-N 0.000 claims 1
- ZTUGTNZSYGNOFE-PVQCJRHBSA-N (2r)-3-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]-1,1,1-trifluoropropan-2-ol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(C[C@@H](O)C(F)(F)F)C1 ZTUGTNZSYGNOFE-PVQCJRHBSA-N 0.000 claims 1
- RJWNXJAXIOIPGQ-KZUDCZAMSA-N (2s)-1-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-methylphenyl]azetidin-1-yl]-2-hydroxypropan-1-one Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(C(=O)[C@H](C)O)C1 RJWNXJAXIOIPGQ-KZUDCZAMSA-N 0.000 claims 1
- FBRKRAOGHVCFCB-SFVWDYPZSA-N (2s)-1-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-methylphenyl]azetidin-1-yl]propan-2-ol Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(C[C@H](C)O)C1 FBRKRAOGHVCFCB-SFVWDYPZSA-N 0.000 claims 1
- GAKDFKQPUPMQJG-ABLWVSNPSA-N (2s)-1-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]-2-hydroxypropan-1-one Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(C(=O)[C@H](C)O)C1 GAKDFKQPUPMQJG-ABLWVSNPSA-N 0.000 claims 1
- CJNJLCYTPKHVSM-ZSOXZCCMSA-N (2s)-1-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]propan-2-ol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(C[C@H](C)O)C1 CJNJLCYTPKHVSM-ZSOXZCCMSA-N 0.000 claims 1
- QKFMWXFSQKPVRN-NUHJPDEHSA-N (2s)-1-[3-[5-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-chloro-2-fluoro-6-methoxyphenyl]azetidin-1-yl]propan-2-ol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(F)=C1C1CN(C[C@H](C)O)C1 QKFMWXFSQKPVRN-NUHJPDEHSA-N 0.000 claims 1
- 125000006595 (C1-C3) alkylsulfinyl group Chemical group 0.000 claims 1
- 125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 claims 1
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 1
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 1
- HQAMOZRQWZASAO-UHFFFAOYSA-N 1-[1-(5-chloro-2-methoxy-4-methyl-3-pyrimidin-5-ylphenyl)ethyl]-3-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical class COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1=CN=CN=C1 HQAMOZRQWZASAO-UHFFFAOYSA-N 0.000 claims 1
- BVQAEDIHXWMDRJ-UHFFFAOYSA-N 1-[1-[3-(2-aminopyrimidin-5-yl)-5-chloro-2-methoxy-4-methylphenyl]ethyl]-3-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1=CN=C(N)N=C1 BVQAEDIHXWMDRJ-UHFFFAOYSA-N 0.000 claims 1
- RMFYBQIIKKPTTD-UHFFFAOYSA-N 1-[1-[4,5-dichloro-3-(1-ethylazetidin-3-yl)-2-methoxyphenyl]ethyl]-3-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1N(CC)CC1C1=C(Cl)C(Cl)=CC(C(C)N2C3=NC=NC(N)=C3C(C)=N2)=C1OC RMFYBQIIKKPTTD-UHFFFAOYSA-N 0.000 claims 1
- DKWCACOYZCVWAR-UHFFFAOYSA-N 1-[1-[5-chloro-2-ethoxy-4-fluoro-3-(1-propan-2-ylazetidin-3-yl)phenyl]ethyl]-3-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(F)=C1C1CN(C(C)C)C1 DKWCACOYZCVWAR-UHFFFAOYSA-N 0.000 claims 1
- FCICEBDJPUNKNB-UHFFFAOYSA-N 1-[1-[5-chloro-2-ethoxy-4-fluoro-3-[1-(2,2,2-trifluoroethyl)azetidin-3-yl]phenyl]ethyl]-3-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(F)=C1C1CN(CC(F)(F)F)C1 FCICEBDJPUNKNB-UHFFFAOYSA-N 0.000 claims 1
- MSXPSGQGKSWASD-UHFFFAOYSA-N 1-[1-[5-chloro-2-ethoxy-4-methyl-3-(1-propan-2-ylazetidin-3-yl)phenyl]ethyl]-3-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(C(C)C)C1 MSXPSGQGKSWASD-UHFFFAOYSA-N 0.000 claims 1
- BVISSWCHEUOQLQ-UHFFFAOYSA-N 1-[1-[5-chloro-2-methoxy-4-methyl-3-(1-methylazetidin-3-yl)phenyl]ethyl]-3-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(C)C1 BVISSWCHEUOQLQ-UHFFFAOYSA-N 0.000 claims 1
- QQLYWGQNVSLCFL-UHFFFAOYSA-N 1-[1-[5-chloro-2-methoxy-4-methyl-3-(1-methylpiperidin-4-yl)phenyl]ethyl]-3-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CCN(C)CC1 QQLYWGQNVSLCFL-UHFFFAOYSA-N 0.000 claims 1
- KVXTVARPRRDFIC-UHFFFAOYSA-N 1-[1-[5-chloro-2-methoxy-4-methyl-3-(1-propan-2-ylazetidin-3-yl)phenyl]ethyl]-3-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(C(C)C)C1 KVXTVARPRRDFIC-UHFFFAOYSA-N 0.000 claims 1
- CELNSDNTUCEZMR-UHFFFAOYSA-N 1-[1-[5-chloro-2-methoxy-4-methyl-3-[1-(2,2,2-trifluoroethyl)azetidin-3-yl]phenyl]ethyl]-3-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(CC(F)(F)F)C1 CELNSDNTUCEZMR-UHFFFAOYSA-N 0.000 claims 1
- IGRFIIIDNJIJPQ-UHFFFAOYSA-N 1-[1-[5-chloro-2-methoxy-4-methyl-3-[1-(2-methylpropyl)azetidin-3-yl]phenyl]ethyl]-3-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(CC(C)C)C1 IGRFIIIDNJIJPQ-UHFFFAOYSA-N 0.000 claims 1
- RTBAGNKTRZBJDQ-UHFFFAOYSA-N 1-[1-[5-chloro-3-(1-ethylazetidin-3-yl)-2-methoxy-4-methylphenyl]ethyl]-3-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1N(CC)CC1C1=C(C)C(Cl)=CC(C(C)N2C3=NC=NC(N)=C3C(C)=N2)=C1OC RTBAGNKTRZBJDQ-UHFFFAOYSA-N 0.000 claims 1
- SJKNIQNKRLFVKE-UHFFFAOYSA-N 1-[1-[5-chloro-3-(1-hydroxyazetidin-3-yl)-2-methoxy-4-methylphenyl]ethyl]-3-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound COc1c(cc(Cl)c(C)c1C1CN(O)C1)C(C)n1nc(C)c2c(N)ncnc12 SJKNIQNKRLFVKE-UHFFFAOYSA-N 0.000 claims 1
- OUELJXRVIBGBSC-UHFFFAOYSA-N 1-[1-[5-chloro-3-[1-(cyclopropylmethyl)azetidin-3-yl]-2-methoxy-4-methylphenyl]ethyl]-3-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C(C1)CN1CC1CC1 OUELJXRVIBGBSC-UHFFFAOYSA-N 0.000 claims 1
- YPLUJLSBEXFVAU-UHFFFAOYSA-N 1-[1-[5-chloro-3-[1-[2-(dimethylamino)ethyl]pyrazol-4-yl]-2-methoxy-4-methylphenyl]ethyl]-3-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C=1C=NN(CCN(C)C)C=1 YPLUJLSBEXFVAU-UHFFFAOYSA-N 0.000 claims 1
- MBAFAGVCOYZNOX-UHFFFAOYSA-N 1-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-fluorophenyl]azetidin-1-yl]-2-methylpropan-2-ol Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(F)=C1C1CN(CC(C)(C)O)C1 MBAFAGVCOYZNOX-UHFFFAOYSA-N 0.000 claims 1
- WSJWSMDGJQMOSH-UHFFFAOYSA-N 1-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-fluorophenyl]azetidin-1-yl]propan-2-ol Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(F)=C1C1CN(CC(C)O)C1 WSJWSMDGJQMOSH-UHFFFAOYSA-N 0.000 claims 1
- PTFWTPFDLLZEPS-UHFFFAOYSA-N 1-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]-2-methylpropan-2-ol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(CC(C)(C)O)C1 PTFWTPFDLLZEPS-UHFFFAOYSA-N 0.000 claims 1
- XFFQYSQURSCESP-UHFFFAOYSA-N 1-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]ethanone Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(C(C)=O)C1 XFFQYSQURSCESP-UHFFFAOYSA-N 0.000 claims 1
- GFOLYFQUUQLCIM-UHFFFAOYSA-N 1-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CC1C1=C(C)C(Cl)=CC(C(C)N2C3=NC=NC(N)=C3C(C)=N2)=C1OC GFOLYFQUUQLCIM-UHFFFAOYSA-N 0.000 claims 1
- HEQBQJMVHVFQFC-UHFFFAOYSA-N 1-[4-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]piperidin-1-yl]-2-methylpropan-2-ol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CCN(CC(C)(C)O)CC1 HEQBQJMVHVFQFC-UHFFFAOYSA-N 0.000 claims 1
- PWGIGBFGHYFIBK-UHFFFAOYSA-N 2-(1-acetylazetidin-3-yl)-4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-methoxybenzonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(C(C)=O)C1 PWGIGBFGHYFIBK-UHFFFAOYSA-N 0.000 claims 1
- WPLLONBBBBTHIP-UHFFFAOYSA-N 2-[1-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]cyclobutyl]acetonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C(C1)CN1C1(CC#N)CCC1 WPLLONBBBBTHIP-UHFFFAOYSA-N 0.000 claims 1
- UWELQOKGACQCNG-UHFFFAOYSA-N 2-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-methylphenyl]azetidin-1-yl]ethanol Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(CCO)C1 UWELQOKGACQCNG-UHFFFAOYSA-N 0.000 claims 1
- VJBZYNUINOYICB-UHFFFAOYSA-N 2-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]-3,3,3-trifluoropropan-1-ol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(C(CO)C(F)(F)F)C1 VJBZYNUINOYICB-UHFFFAOYSA-N 0.000 claims 1
- DVVNMGCJKBIXHN-UHFFFAOYSA-N 2-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]acetonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(CC#N)C1 DVVNMGCJKBIXHN-UHFFFAOYSA-N 0.000 claims 1
- JBCBZHKCOKPHKX-UHFFFAOYSA-N 2-[3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]azetidin-1-yl]ethanol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CN(CCO)C1 JBCBZHKCOKPHKX-UHFFFAOYSA-N 0.000 claims 1
- QCNVWRCCTQZPQV-UHFFFAOYSA-N 2-[3-[5-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-chloro-2-cyano-6-ethoxyphenyl]azetidin-1-yl]-2-methylpropanamide Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(C(C)(C)C(N)=O)C1 QCNVWRCCTQZPQV-UHFFFAOYSA-N 0.000 claims 1
- MLARYDAXPYMQPL-UHFFFAOYSA-N 2-[3-[5-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-chloro-2-fluoro-6-methoxyphenyl]azetidin-1-yl]ethanol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(F)=C1C1CN(CCO)C1 MLARYDAXPYMQPL-UHFFFAOYSA-N 0.000 claims 1
- CTMFIZNSBDRCIE-UHFFFAOYSA-N 2-[4-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-methylphenyl]pyrazol-1-yl]acetamide Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C=1C=NN(CC(N)=O)C=1 CTMFIZNSBDRCIE-UHFFFAOYSA-N 0.000 claims 1
- BXONZXFPKQOFNN-UHFFFAOYSA-N 2-[4-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]pyrazol-1-yl]ethanol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C=1C=NN(CCO)C=1 BXONZXFPKQOFNN-UHFFFAOYSA-N 0.000 claims 1
- VZCBKGOVKCOFDS-UHFFFAOYSA-N 2-[5-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]pyridin-2-yl]oxyethanol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1=CC=C(OCCO)N=C1 VZCBKGOVKCOFDS-UHFFFAOYSA-N 0.000 claims 1
- UXTGQWWQMSXIHY-UHFFFAOYSA-N 2-[[5-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]pyridin-2-yl]amino]ethanol Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1=CC=C(NCCO)N=C1 UXTGQWWQMSXIHY-UHFFFAOYSA-N 0.000 claims 1
- CWCRGAQAZXYCCJ-UHFFFAOYSA-N 3-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]-n-methylazetidine-1-carboxamide Chemical compound C1N(C(=O)NC)CC1C1=C(C)C(Cl)=CC(C(C)N2C3=NC=NC(N)=C3C(C)=N2)=C1OC CWCRGAQAZXYCCJ-UHFFFAOYSA-N 0.000 claims 1
- FRRSLHDFEVZTPH-UHFFFAOYSA-N 3-[5-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-chloro-2-cyano-6-methoxyphenyl]-n,n-dimethylazetidine-1-carboxamide Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(C(=O)N(C)C)C1 FRRSLHDFEVZTPH-UHFFFAOYSA-N 0.000 claims 1
- NGSFHDXBDLNNPM-UHFFFAOYSA-N 3-[5-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-chloro-2-cyano-6-methoxyphenyl]-n-tert-butylazetidine-1-carboxamide Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(C(=O)NC(C)(C)C)C1 NGSFHDXBDLNNPM-UHFFFAOYSA-N 0.000 claims 1
- MJVXTRGIJKQFHG-UHFFFAOYSA-N 3-[5-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-chloro-2-cyano-6-methoxyphenyl]azetidine-1-carboxamide Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(C(N)=O)C1 MJVXTRGIJKQFHG-UHFFFAOYSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- XGARCYYYFPWMKC-IAPIXIRKSA-N 4-[(1R)-1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-ethoxy-2-(2-oxo-1,3-oxazolidin-5-yl)benzonitrile Chemical compound CCOc1c(cc(Cl)c(C#N)c1C1CNC(=O)O1)[C@@H](C)n1nc(C)c2c(N)ncnc12 XGARCYYYFPWMKC-IAPIXIRKSA-N 0.000 claims 1
- ITEITQVKTJSFFX-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-2-(azetidin-3-yl)-6-chloro-3-ethoxybenzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CNC1 ITEITQVKTJSFFX-UHFFFAOYSA-N 0.000 claims 1
- PNRYWUJRDIJNKG-CFMCSPIPSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-2-[1-[(2s)-2-hydroxypropyl]azetidin-3-yl]-3-methoxy-6-methylbenzonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(C)C(C#N)=C1C1CN(C[C@H](C)O)C1 PNRYWUJRDIJNKG-CFMCSPIPSA-N 0.000 claims 1
- IECAGZBMWJQJMS-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-ethoxy-6-methyl-2-(1-propan-2-ylazetidin-3-yl)benzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(C)C(C#N)=C1C1CN(C(C)C)C1 IECAGZBMWJQJMS-UHFFFAOYSA-N 0.000 claims 1
- ZYYBPQOUQVKJNI-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-2-[1-(2-hydroxyethyl)azetidin-3-yl]-3-methoxybenzonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(CCO)C1 ZYYBPQOUQVKJNI-UHFFFAOYSA-N 0.000 claims 1
- KLKCQNBHXXLCHY-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-2-[1-(2-hydroxypropyl)azetidin-3-yl]-3-methoxybenzonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(CC(C)O)C1 KLKCQNBHXXLCHY-UHFFFAOYSA-N 0.000 claims 1
- KLKCQNBHXXLCHY-AMGKYWFPSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-2-[1-[(2s)-2-hydroxypropyl]azetidin-3-yl]-3-methoxybenzonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(C[C@H](C)O)C1 KLKCQNBHXXLCHY-AMGKYWFPSA-N 0.000 claims 1
- VXDSZRICEQLKCZ-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-ethoxy-2-(1-methylazetidin-3-yl)benzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(C)C1 VXDSZRICEQLKCZ-UHFFFAOYSA-N 0.000 claims 1
- FZASTEUHBGGYAL-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-ethoxy-2-(3-methoxyazetidin-1-yl)benzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1N1CC(OC)C1 FZASTEUHBGGYAL-UHFFFAOYSA-N 0.000 claims 1
- IIEKNYURGTYVMT-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-ethoxy-2-(5-oxopyrrolidin-3-yl)benzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CNC(=O)C1 IIEKNYURGTYVMT-UHFFFAOYSA-N 0.000 claims 1
- MCIRQIFXNINZHL-NBFOIZRFSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-ethoxy-2-[1-[(2s)-2-hydroxypropyl]azetidin-3-yl]benzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(C[C@H](C)O)C1 MCIRQIFXNINZHL-NBFOIZRFSA-N 0.000 claims 1
- GZPOZNLKRAMBLT-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-ethoxy-2-pyrrolidin-1-ylbenzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1N1CCCC1 GZPOZNLKRAMBLT-UHFFFAOYSA-N 0.000 claims 1
- DBKSCUIVQFGLEJ-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-methoxy-2-(1-methylazetidin-3-yl)benzonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(C)C1 DBKSCUIVQFGLEJ-UHFFFAOYSA-N 0.000 claims 1
- OWQMJTFVVTZJKY-UHFFFAOYSA-N 4-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-6-chloro-3-methoxy-2-(1-methylsulfonylazetidin-3-yl)benzonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1CN(S(C)(=O)=O)C1 OWQMJTFVVTZJKY-UHFFFAOYSA-N 0.000 claims 1
- PPURAVRTZVKOKD-UHFFFAOYSA-N 4-[1-(4-amino-5-methylpyrrolo[2,3-d]pyrimidin-7-yl)ethyl]-6-chloro-3-ethoxy-2-(1-propan-2-ylazetidin-3-yl)benzonitrile Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=C2)C=C(Cl)C(C#N)=C1C1CN(C(C)C)C1 PPURAVRTZVKOKD-UHFFFAOYSA-N 0.000 claims 1
- UCYDWQYLQRHHCX-UHFFFAOYSA-N 4-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-fluorophenyl]-1,3-oxazolidin-2-one Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(F)=C1C1COC(=O)N1 UCYDWQYLQRHHCX-UHFFFAOYSA-N 0.000 claims 1
- ZQPDJCIXJHUERQ-UHFFFAOYSA-N 4-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-fluorophenyl]pyrrolidin-2-one Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(F)=C1C1CNC(=O)C1 ZQPDJCIXJHUERQ-UHFFFAOYSA-N 0.000 claims 1
- DCYPFCXQPSHQAV-UHFFFAOYSA-N 4-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]-2-fluoro-n,n-dimethylbenzamide Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1=CC=C(C(=O)N(C)C)C(F)=C1 DCYPFCXQPSHQAV-UHFFFAOYSA-N 0.000 claims 1
- NJMVVKSDTMRUPW-UHFFFAOYSA-N 4-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]-2-fluoro-n-methylbenzamide Chemical compound C1=C(F)C(C(=O)NC)=CC=C1C1=C(C)C(Cl)=CC(C(C)N2C3=NC=NC(N)=C3C(C)=N2)=C1OC NJMVVKSDTMRUPW-UHFFFAOYSA-N 0.000 claims 1
- SMTNSBXQKKGWLV-UHFFFAOYSA-N 4-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]-n-(2-hydroxyethyl)pyridine-2-carboxamide Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1=CC=NC(C(=O)NCCO)=C1 SMTNSBXQKKGWLV-UHFFFAOYSA-N 0.000 claims 1
- SKAPLEFCLYIUAU-UHFFFAOYSA-N 4-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(C=2C(=C(C(C)N3C4=NC=NC(N)=C4C(C)=N3)C=C(Cl)C=2C)OC)=C1 SKAPLEFCLYIUAU-UHFFFAOYSA-N 0.000 claims 1
- CGOOTFVIDYUBGF-UHFFFAOYSA-N 4-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-cyano-2-methoxy-6-methylphenyl]-n-(2-hydroxyethyl)-n-methylpyridine-2-carboxamide Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(C#N)C(C)=C1C1=CC=NC(C(=O)N(C)CCO)=C1 CGOOTFVIDYUBGF-UHFFFAOYSA-N 0.000 claims 1
- PFWHUFUHASEOFP-UHFFFAOYSA-N 5-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-4-methoxy-2-methyl-3-(1-methylpyrazol-4-yl)benzonitrile Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(C#N)C(C)=C1C=1C=NN(C)C=1 PFWHUFUHASEOFP-UHFFFAOYSA-N 0.000 claims 1
- OFKSVBCPWKARPM-UHFFFAOYSA-N 5-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-(2,2-difluoroethoxy)-6-methylphenyl]-n,n-dimethylpyridine-2-carboxamide Chemical compound N1=C(C)C2=C(N)N=CN=C2N1C(C)C(C=1OCC(F)F)=CC(Cl)=C(C)C=1C1=CC=C(C(=O)N(C)C)N=C1 OFKSVBCPWKARPM-UHFFFAOYSA-N 0.000 claims 1
- NENZZUFAAHFIPT-UHFFFAOYSA-N 5-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-fluorophenyl]-1,3-oxazolidin-2-one Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(F)=C1C1CNC(=O)O1 NENZZUFAAHFIPT-UHFFFAOYSA-N 0.000 claims 1
- NIZYKSCTQPOPRY-UHFFFAOYSA-N 5-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]-1,3-oxazolidin-2-one Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CNC(=O)O1 NIZYKSCTQPOPRY-UHFFFAOYSA-N 0.000 claims 1
- KATAAFRJKJMWFE-UHFFFAOYSA-N 5-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]-n,n-dimethylpyridine-3-carboxamide Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1=CN=CC(C(=O)N(C)C)=C1 KATAAFRJKJMWFE-UHFFFAOYSA-N 0.000 claims 1
- MRVLFHBXSHLHOL-UHFFFAOYSA-N 5-[3-[1-(4-amino-3-methylpyrazolo[4,3-c]pyridin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]-n,n-dimethylpyridine-2-carboxamide Chemical compound COC1=C(C(C)N2C3=CC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1=CC=C(C(=O)N(C)C)N=C1 MRVLFHBXSHLHOL-UHFFFAOYSA-N 0.000 claims 1
- WKGUYEULKUKCFJ-UHFFFAOYSA-N 5-[5-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-3-chloro-2-cyano-6-ethoxyphenyl]-n,n-dimethylpyridine-2-carboxamide Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C#N)=C1C1=CC=C(C(=O)N(C)C)N=C1 WKGUYEULKUKCFJ-UHFFFAOYSA-N 0.000 claims 1
- NRCSKGTXJHFFMV-UHFFFAOYSA-N 6-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-methylphenyl]-n,n-dimethylpyridine-3-carboxamide Chemical compound CCOC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1=CC=C(C(=O)N(C)C)C=N1 NRCSKGTXJHFFMV-UHFFFAOYSA-N 0.000 claims 1
- SCBCNLJYIPIGFY-UHFFFAOYSA-N 6-[3-[1-(4-amino-3-methylpyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl]morpholin-3-one Chemical compound COC1=C(C(C)N2C3=NC=NC(N)=C3C(C)=N2)C=C(Cl)C(C)=C1C1CNC(=O)CO1 SCBCNLJYIPIGFY-UHFFFAOYSA-N 0.000 claims 1
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims 1
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims 1
- 208000032671 Allergic granulomatous angiitis Diseases 0.000 claims 1
- 208000003950 B-cell lymphoma Diseases 0.000 claims 1
- 208000033386 Buerger disease Diseases 0.000 claims 1
- 208000006344 Churg-Strauss Syndrome Diseases 0.000 claims 1
- 208000010007 Cogan syndrome Diseases 0.000 claims 1
- 208000019707 Cryoglobulinemic vasculitis Diseases 0.000 claims 1
- 208000018428 Eosinophilic granulomatosis with polyangiitis Diseases 0.000 claims 1
- 208000007465 Giant cell arteritis Diseases 0.000 claims 1
- 206010018691 Granuloma Diseases 0.000 claims 1
- 206010072579 Granulomatosis with polyangiitis Diseases 0.000 claims 1
- 208000032843 Hemorrhage Diseases 0.000 claims 1
- 208000017604 Hodgkin disease Diseases 0.000 claims 1
- 208000021519 Hodgkin lymphoma Diseases 0.000 claims 1
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims 1
- 206010020631 Hypergammaglobulinaemia benign monoclonal Diseases 0.000 claims 1
- 208000019758 Hypergammaglobulinemia Diseases 0.000 claims 1
- 208000011200 Kawasaki disease Diseases 0.000 claims 1
- 208000034624 Leukocytoclastic Cutaneous Vasculitis Diseases 0.000 claims 1
- 208000032514 Leukocytoclastic vasculitis Diseases 0.000 claims 1
- 206010029461 Nodal marginal zone B-cell lymphomas Diseases 0.000 claims 1
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 1
- 208000007452 Plasmacytoma Diseases 0.000 claims 1
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 1
- 208000033766 Prolymphocytic Leukemia Diseases 0.000 claims 1
- 208000004732 Systemic Vasculitis Diseases 0.000 claims 1
- 208000001106 Takayasu Arteritis Diseases 0.000 claims 1
- 208000033559 Waldenström macroglobulinemia Diseases 0.000 claims 1
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims 1
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 1
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 1
- 210000003719 b-lymphocyte Anatomy 0.000 claims 1
- 208000034158 bleeding Diseases 0.000 claims 1
- 230000000740 bleeding effect Effects 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 208000010353 central nervous system vasculitis Diseases 0.000 claims 1
- 201000003278 cryoglobulinemia Diseases 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 230000001086 cytosolic effect Effects 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 201000006569 extramedullary plasmacytoma Diseases 0.000 claims 1
- 230000003325 follicular Effects 0.000 claims 1
- 210000001102 germinal center b cell Anatomy 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 201000006362 hypersensitivity vasculitis Diseases 0.000 claims 1
- 208000026876 intravascular large B-cell lymphoma Diseases 0.000 claims 1
- 210000003563 lymphoid tissue Anatomy 0.000 claims 1
- 201000000564 macroglobulinemia Diseases 0.000 claims 1
- 210000001161 mammalian embryo Anatomy 0.000 claims 1
- 201000007924 marginal zone B-cell lymphoma Diseases 0.000 claims 1
- 208000021937 marginal zone lymphoma Diseases 0.000 claims 1
- 206010063344 microscopic polyangiitis Diseases 0.000 claims 1
- 201000005328 monoclonal gammopathy of uncertain significance Diseases 0.000 claims 1
- 208000001725 mucocutaneous lymph node syndrome Diseases 0.000 claims 1
- 210000004877 mucosa Anatomy 0.000 claims 1
- 206010028537 myelofibrosis Diseases 0.000 claims 1
- 201000000050 myeloid neoplasm Diseases 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 201000006039 nodal marginal zone lymphoma Diseases 0.000 claims 1
- 208000031223 plasma cell leukemia Diseases 0.000 claims 1
- 210000004180 plasmocyte Anatomy 0.000 claims 1
- OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims 1
- 230000000306 recurrent effect Effects 0.000 claims 1
- 208000010721 smoldering plasma cell myeloma Diseases 0.000 claims 1
- 206010062113 splenic marginal zone lymphoma Diseases 0.000 claims 1
- 206010043207 temporal arteritis Diseases 0.000 claims 1
- 210000001541 thymus gland Anatomy 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361771480P | 2013-03-01 | 2013-03-01 | |
| US61/771,480 | 2013-03-01 | ||
| PCT/US2014/019372 WO2014134426A1 (en) | 2013-03-01 | 2014-02-28 | USE OF PYRAZOLOPYRIMIDINE DERIVATIVES FOR THE TREATMENT OF PI3Kδ RELATED DISORDERS |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019084393A Division JP6776399B2 (ja) | 2013-03-01 | 2019-04-25 | ＰＩ３Ｋδ関連障害治療のためのピラゾロピリミジン誘導体の使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016510035A JP2016510035A (ja) | 2016-04-04 |
| JP2016510035A5 true JP2016510035A5 (https=) | 2017-04-13 |
| JP6545106B2 JP6545106B2 (ja) | 2019-07-17 |
Family
ID=50288319
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015560346A Active JP6545106B2 (ja) | 2013-03-01 | 2014-02-28 | ＰＩ３Ｋδ関連障害治療のためのピラゾロピリミジン誘導体の使用 |
| JP2019084393A Active JP6776399B2 (ja) | 2013-03-01 | 2019-04-25 | ＰＩ３Ｋδ関連障害治療のためのピラゾロピリミジン誘導体の使用 |
| JP2020169551A Active JP7189185B2 (ja) | 2013-03-01 | 2020-10-07 | ＰＩ３Ｋδ関連障害治療のためのピラゾロピリミジン誘導体の使用 |
| JP2022192954A Active JP7556010B2 (ja) | 2013-03-01 | 2022-12-01 | ＰＩ３Ｋδ関連障害治療のためのピラゾロピリミジン誘導体の使用 |
| JP2024157116A Pending JP2025003975A (ja) | 2013-03-01 | 2024-09-11 | ＰＩ３Ｋδ関連障害治療のためのピラゾロピリミジン誘導体の使用 |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019084393A Active JP6776399B2 (ja) | 2013-03-01 | 2019-04-25 | ＰＩ３Ｋδ関連障害治療のためのピラゾロピリミジン誘導体の使用 |
| JP2020169551A Active JP7189185B2 (ja) | 2013-03-01 | 2020-10-07 | ＰＩ３Ｋδ関連障害治療のためのピラゾロピリミジン誘導体の使用 |
| JP2022192954A Active JP7556010B2 (ja) | 2013-03-01 | 2022-12-01 | ＰＩ３Ｋδ関連障害治療のためのピラゾロピリミジン誘導体の使用 |
| JP2024157116A Pending JP2025003975A (ja) | 2013-03-01 | 2024-09-11 | ＰＩ３Ｋδ関連障害治療のためのピラゾロピリミジン誘導体の使用 |
Country Status (32)
| Country | Link |
|---|---|
| US (6) | US9932341B2 (https=) |
| EP (3) | EP2961410B1 (https=) |
| JP (5) | JP6545106B2 (https=) |
| KR (5) | KR20240152422A (https=) |
| CN (2) | CN105120871B (https=) |
| AR (1) | AR094964A1 (https=) |
| AU (5) | AU2014223257B2 (https=) |
| BR (1) | BR112015020941A2 (https=) |
| CA (1) | CA2901993C (https=) |
| CL (1) | CL2015002442A1 (https=) |
| CR (1) | CR20150472A (https=) |
| CY (1) | CY1122712T1 (https=) |
| DK (1) | DK2961410T3 (https=) |
| EA (2) | EA202192151A1 (https=) |
| ES (2) | ES2945212T3 (https=) |
| HR (1) | HRP20200263T1 (https=) |
| HU (1) | HUE047719T2 (https=) |
| IL (6) | IL311666A (https=) |
| LT (1) | LT2961410T (https=) |
| MX (2) | MX367713B (https=) |
| MY (1) | MY177875A (https=) |
| PE (1) | PE20151996A1 (https=) |
| PH (3) | PH12021552233A1 (https=) |
| PL (1) | PL2961410T3 (https=) |
| PT (1) | PT2961410T (https=) |
| RS (1) | RS59958B1 (https=) |
| SG (3) | SG10201707130UA (https=) |
| SI (1) | SI2961410T1 (https=) |
| SM (1) | SMT202000043T1 (https=) |
| TW (5) | TWI687220B (https=) |
| UA (1) | UA119641C2 (https=) |
| WO (1) | WO2014134426A1 (https=) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104945420A (zh) | 2009-06-29 | 2015-09-30 | 因塞特公司 | 作为pi3k抑制剂的嘧啶酮类 |
| KR102507287B1 (ko) | 2011-09-02 | 2023-03-07 | 인사이트 홀딩스 코포레이션 | Ｐｉ３ｋ 억제제로서 헤테로시클릴아민 |
| AR090548A1 (es) | 2012-04-02 | 2014-11-19 | Incyte Corp | Azaheterociclobencilaminas biciclicas como inhibidores de pi3k |
| JP6437452B2 (ja) | 2013-01-14 | 2018-12-12 | インサイト・ホールディングス・コーポレイションＩｎｃｙｔｅ Ｈｏｌｄｉｎｇｓ Ｃｏｒｐｏｒａｔｉｏｎ | Ｐｉｍキナーゼ阻害剤として有用な二環式芳香族カルボキサミド化合物 |
| RS60244B1 (sr) | 2013-01-15 | 2020-06-30 | Incyte Holdings Corp | Jedinjenja tiazolkarboksamida i piridinkarboksamida korisna kao inhibitori pim kinaze |
| TWI687220B (zh) * | 2013-03-01 | 2020-03-11 | 美商英塞特控股公司 | 吡唑并嘧啶衍生物治療PI3Kδ相關病症之用途 |
| CN105658653A (zh) | 2013-08-23 | 2016-06-08 | 因赛特公司 | 可用作pim激酶抑制剂的呋喃并-和噻吩并-吡啶甲酰胺化合物 |
| PH12020552277A1 (en) | 2014-04-08 | 2023-07-17 | Incyte Holdings Corp | Treatment of b-cell malignancies by a combination jak and pi3k inhibitor |
| WO2015191677A1 (en) | 2014-06-11 | 2015-12-17 | Incyte Corporation | Bicyclic heteroarylaminoalkyl phenyl derivatives as pi3k inhibitors |
| WO2016010897A1 (en) | 2014-07-14 | 2016-01-21 | Incyte Corporation | Bicyclic heteroaromatic carboxamide compounds useful as pim kinase inhibitors |
| US9580418B2 (en) | 2014-07-14 | 2017-02-28 | Incyte Corporation | Bicyclic aromatic carboxamide compounds useful as Pim kinase inhibitors |
| WO2016130501A1 (en) | 2015-02-09 | 2016-08-18 | Incyte Corporation | Aza-heteroaryl compounds as pi3k-gamma inhibitors |
| SI3831833T1 (sl) * | 2015-02-27 | 2023-03-31 | Incyte Holdings Corporation | Postopki za pripravo inhibitorja PI3K |
| US9988401B2 (en) | 2015-05-11 | 2018-06-05 | Incyte Corporation | Crystalline forms of a PI3K inhibitor |
| WO2016196244A1 (en) | 2015-05-29 | 2016-12-08 | Incyte Corporation | Pyridineamine compounds useful as pim kinase inhibitors |
| TWI734699B (zh) | 2015-09-09 | 2021-08-01 | 美商英塞特公司 | Ｐｉｍ激酶抑制劑之鹽 |
| US9920032B2 (en) | 2015-10-02 | 2018-03-20 | Incyte Corporation | Heterocyclic compounds useful as pim kinase inhibitors |
| RS63359B1 (sr) | 2015-11-06 | 2022-07-29 | Incyte Corp | Heterociklična jedinjenja kao inhibitori pi3k-gama |
| WO2017120194A1 (en) | 2016-01-05 | 2017-07-13 | Incyte Corporation | Pyridine and pyridimine compounds as pi3k-gamma inhibitors |
| EP3795563B1 (en) | 2016-03-31 | 2024-07-17 | Oncternal Therapeutics, Inc. | Indoline analogs and uses thereof |
| WO2017223414A1 (en) | 2016-06-24 | 2017-12-28 | Incyte Corporation | HETEROCYCLIC COMPOUNDS AS PI3K-γ INHIBITORS |
| TWI817956B (zh) * | 2017-09-08 | 2023-10-11 | 英屬開曼群島商百濟神州有限公司 | 咪唑並[1,5-A]吡嗪衍生物作爲PI3Kδ 抑制劑 |
| KR20240152947A (ko) | 2017-10-18 | 2024-10-22 | 인사이트 코포레이션 | Pi3k-감마 저해제로서의 3차 하이드록시기로 치환된 축합된 이미다졸 유도체 |
| AR113922A1 (es) | 2017-12-08 | 2020-07-01 | Incyte Corp | Terapia de combinación de dosis baja para el tratamiento de neoplasias mieloproliferativas |
| EP3737684B1 (en) * | 2018-01-10 | 2022-11-16 | Idorsia Pharmaceuticals Ltd | 2,4,6,7-tetrahydro-pyrazolo[4,3-d]pyrimidin-5-one derivatives and related compounds as c5a receptor modulators for treating vasculitis and inflammatory diseases |
| BR112020018094A2 (pt) | 2018-03-08 | 2020-12-22 | Incyte Corporation | Compostos de aminopirazina diol como inibidores de pi3k-¿ |
| CA3101323A1 (en) * | 2018-06-01 | 2019-12-05 | Incyte Corporation | Dosing regimen for the treatment of pi3k related disorders |
| US11046658B2 (en) | 2018-07-02 | 2021-06-29 | Incyte Corporation | Aminopyrazine derivatives as PI3K-γ inhibitors |
| TWI727392B (zh) * | 2018-08-13 | 2021-05-11 | 美商基利科學股份有限公司 | 噻二唑irak4抑制劑 |
| CN110833552A (zh) * | 2018-08-15 | 2020-02-25 | 广西梧州制药（集团）股份有限公司 | 吡唑并嘧啶衍生物在治疗狼疮肾炎的用途 |
| CR20250050A (es) * | 2018-09-05 | 2025-03-19 | Incyte Corp | Formas cristalinas de un inhibidor de fosfoinositida 3–quinasa (pi3k) (divisional 2021-0165) |
| WO2022115120A1 (en) | 2020-11-30 | 2022-06-02 | Incyte Corporation | Combination therapy with an anti-cd19 antibody and parsaclisib |
| CA3203587A1 (en) | 2020-11-30 | 2022-06-02 | Incyte Corporation | Combination therapy with an anti-cd19 antibody and parsaclisib |
| CN112808550B (zh) * | 2020-12-28 | 2021-10-01 | 青岛理工大学 | 用于海洋工程的劣化免疫仿生防护界面及制备方法 |
| US20230190755A1 (en) | 2021-12-16 | 2023-06-22 | Incyte Corporation | Topical formulations of PI3K-delta inhibitors |
Family Cites Families (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5521184A (en) | 1992-04-03 | 1996-05-28 | Ciba-Geigy Corporation | Pyrimidine derivatives and processes for the preparation thereof |
| ATE459616T1 (de) | 1998-08-11 | 2010-03-15 | Novartis Ag | Isochinoline derivate mit angiogenesis-hemmender wirkung |
| US6133031A (en) | 1999-08-19 | 2000-10-17 | Isis Pharmaceuticals Inc. | Antisense inhibition of focal adhesion kinase expression |
| GB9905075D0 (en) | 1999-03-06 | 1999-04-28 | Zeneca Ltd | Chemical compounds |
| GB0004890D0 (en) | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
| ATE273695T1 (de) | 2000-06-28 | 2004-09-15 | Smithkline Beecham Plc | Nassvermahlung |
| IL160915A0 (en) | 2001-09-19 | 2004-08-31 | Aventis Pharma Sa | Indolizines inhibiting kinase proteins |
| ES2269793T3 (es) | 2001-10-30 | 2007-04-01 | Novartis Ag | Derivados de estaurospina como inhibidores de la actividad de tirosina quinasa receptora flt3. |
| TW200406374A (en) | 2002-05-29 | 2004-05-01 | Novartis Ag | Diaryl urea derivatives useful for the treatment of protein kinase dependent diseases |
| GB0215676D0 (en) | 2002-07-05 | 2002-08-14 | Novartis Ag | Organic compounds |
| CL2003002353A1 (es) | 2002-11-15 | 2005-02-04 | Vertex Pharma | Compuestos derivados de diaminotriazoles, inhibidores d ela proteina quinasa; composicion farmaceutica; procedimiento de preparacion; y su uso del compuesto en el tratamiento de enfermedades de desordenes alergicos, proliferacion, autoinmunes, condic |
| UA80767C2 (en) | 2002-12-20 | 2007-10-25 | Pfizer Prod Inc | Pyrimidine derivatives for the treatment of abnormal cell growth |
| GB0305929D0 (en) | 2003-03-14 | 2003-04-23 | Novartis Ag | Organic compounds |
| AR045944A1 (es) | 2003-09-24 | 2005-11-16 | Novartis Ag | Derivados de isoquinolina 1.4-disustituidas |
| JP4688876B2 (ja) | 2004-06-10 | 2011-05-25 | アイアールエム・リミテッド・ライアビリティ・カンパニー | タンパク質キナーゼ阻害剤としての化合物および組成物 |
| RU2007123675A (ru) | 2004-11-24 | 2008-12-27 | Новартис АГ (CH) | Комбинации ингибиторов jak |
| CN102532133A (zh) | 2006-01-17 | 2012-07-04 | 沃泰克斯药物股份有限公司 | 适用作詹纳斯激酶抑制剂的吖吲哚类 |
| TW200916447A (en) | 2007-08-29 | 2009-04-16 | Methylgene Inc | Sirtuin inhibitors |
| EP2310391A1 (en) | 2008-06-27 | 2011-04-20 | S*BIO Pte Ltd | Pyrazine substituted purines |
| AR073651A1 (es) * | 2008-09-24 | 2010-11-24 | Novartis Ag | Formulaciones galenicas de compuestos organicos |
| US8703778B2 (en) * | 2008-09-26 | 2014-04-22 | Intellikine Llc | Heterocyclic kinase inhibitors |
| CA2754343A1 (en) | 2009-04-09 | 2010-10-14 | Oncothyreon, Inc. | Methods and compositions of pi-3 kinase inhibitors for treating fibrosis |
| CN104945420A (zh) | 2009-06-29 | 2015-09-30 | 因塞特公司 | 作为pi3k抑制剂的嘧啶酮类 |
| US8293753B2 (en) | 2009-07-02 | 2012-10-23 | Novartis Ag | Substituted 2-carboxamide cycloamino ureas |
| ES2432315T3 (es) | 2009-08-28 | 2013-12-02 | Takeda Pharmaceutical Company Limited | Compuestos de hexahidrooxazinopterina para su uso como inhibidores de mTOR |
| WO2011075643A1 (en) | 2009-12-18 | 2011-06-23 | Incyte Corporation | Substituted heteroaryl fused derivatives as pi3k inhibitors |
| US8680108B2 (en) | 2009-12-18 | 2014-03-25 | Incyte Corporation | Substituted fused aryl and heteroaryl 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 |
| WO2012106343A2 (en) | 2011-02-01 | 2012-08-09 | The Board Of Trustees Of The University Of Illinois | Hdac inhibitors and therapeutic methods using the same |
| 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 |
| KR102507287B1 (ko) | 2011-09-02 | 2023-03-07 | 인사이트 홀딩스 코포레이션 | Ｐｉ３ｋ 억제제로서 헤테로시클릴아민 |
| AR090548A1 (es) | 2012-04-02 | 2014-11-19 | Incyte Corp | Azaheterociclobencilaminas biciclicas como inhibidores de pi3k |
| TWI687220B (zh) * | 2013-03-01 | 2020-03-11 | 美商英塞特控股公司 | 吡唑并嘧啶衍生物治療PI3Kδ相關病症之用途 |
| WO2015191677A1 (en) * | 2014-06-11 | 2015-12-17 | Incyte Corporation | Bicyclic heteroarylaminoalkyl phenyl derivatives as pi3k inhibitors |
| SI3831833T1 (sl) * | 2015-02-27 | 2023-03-31 | Incyte Holdings Corporation | Postopki za pripravo inhibitorja PI3K |
| CA3101323A1 (en) * | 2018-06-01 | 2019-12-05 | Incyte Corporation | Dosing regimen for the treatment of pi3k related disorders |
| US11161838B2 (en) * | 2018-11-13 | 2021-11-02 | Incyte Corporation | Heterocyclic derivatives as PI3K inhibitors |
-
2014
- 2014-02-27 TW TW108100664A patent/TWI687220B/zh active
- 2014-02-27 TW TW109104878A patent/TWI736135B/zh active
- 2014-02-27 TW TW110124946A patent/TW202214254A/zh unknown
- 2014-02-27 TW TW103106906A patent/TWI657090B/zh active
- 2014-02-27 TW TW112117019A patent/TWI841376B/zh active
- 2014-02-28 JP JP2015560346A patent/JP6545106B2/ja active Active
- 2014-02-28 KR KR1020247033698A patent/KR20240152422A/ko active Pending
- 2014-02-28 EA EA202192151A patent/EA202192151A1/ru unknown
- 2014-02-28 HU HUE14710739A patent/HUE047719T2/hu unknown
- 2014-02-28 PL PL14710739T patent/PL2961410T3/pl unknown
- 2014-02-28 KR KR1020157027010A patent/KR102298150B1/ko active Active
- 2014-02-28 AR ARP140100679A patent/AR094964A1/es unknown
- 2014-02-28 LT LTEP14710739.5T patent/LT2961410T/lt unknown
- 2014-02-28 PT PT147107395T patent/PT2961410T/pt unknown
- 2014-02-28 WO PCT/US2014/019372 patent/WO2014134426A1/en not_active Ceased
- 2014-02-28 PH PH1/2021/552233A patent/PH12021552233A1/en unknown
- 2014-02-28 MY MYPI2015002108A patent/MY177875A/en unknown
- 2014-02-28 DK DK14710739.5T patent/DK2961410T3/da active
- 2014-02-28 KR KR1020227035039A patent/KR102586858B1/ko active Active
- 2014-02-28 SG SG10201707130UA patent/SG10201707130UA/en unknown
- 2014-02-28 US US14/193,481 patent/US9932341B2/en active Active
- 2014-02-28 HR HRP20200263TT patent/HRP20200263T1/hr unknown
- 2014-02-28 SI SI201431449T patent/SI2961410T1/sl unknown
- 2014-02-28 ES ES19208523T patent/ES2945212T3/es active Active
- 2014-02-28 EP EP14710739.5A patent/EP2961410B1/en active Active
- 2014-02-28 EP EP23161858.8A patent/EP4233869A3/en active Pending
- 2014-02-28 IL IL311666A patent/IL311666A/en unknown
- 2014-02-28 KR KR1020237033761A patent/KR102717616B1/ko active Active
- 2014-02-28 EA EA201591612A patent/EA201591612A1/ru unknown
- 2014-02-28 KR KR1020217027697A patent/KR102454308B1/ko active Active
- 2014-02-28 SG SG10201912275YA patent/SG10201912275YA/en unknown
- 2014-02-28 UA UAA201509435A patent/UA119641C2/uk unknown
- 2014-02-28 CA CA2901993A patent/CA2901993C/en active Active
- 2014-02-28 EP EP19208523.1A patent/EP3632442B1/en active Active
- 2014-02-28 BR BR112015020941A patent/BR112015020941A2/pt not_active Application Discontinuation
- 2014-02-28 IL IL301180A patent/IL301180A/en unknown
- 2014-02-28 RS RS20200176A patent/RS59958B1/sr unknown
- 2014-02-28 SG SG11201506654UA patent/SG11201506654UA/en unknown
- 2014-02-28 ES ES14710739T patent/ES2774436T3/es active Active
- 2014-02-28 CN CN201480021187.1A patent/CN105120871B/zh active Active
- 2014-02-28 SM SM20200043T patent/SMT202000043T1/it unknown
- 2014-02-28 CN CN201810796220.8A patent/CN109010343A/zh active Pending
- 2014-02-28 PE PE2015001833A patent/PE20151996A1/es not_active Application Discontinuation
- 2014-02-28 AU AU2014223257A patent/AU2014223257B2/en active Active
- 2014-02-28 MX MX2015011273A patent/MX367713B/es active IP Right Grant
-
2015
- 2015-08-24 IL IL240784A patent/IL240784B/en not_active IP Right Cessation
- 2015-08-28 MX MX2019010422A patent/MX2019010422A/es unknown
- 2015-08-31 CL CL2015002442A patent/CL2015002442A1/es unknown
- 2015-09-01 PH PH12015501920A patent/PH12015501920A1/en unknown
- 2015-09-10 CR CR20150472A patent/CR20150472A/es unknown
-
2018
- 2018-03-02 US US15/910,708 patent/US20190040067A1/en not_active Abandoned
- 2018-11-14 AU AU2018264053A patent/AU2018264053B2/en active Active
-
2019
- 2019-04-25 JP JP2019084393A patent/JP6776399B2/ja active Active
- 2019-06-11 PH PH12019501321A patent/PH12019501321A1/en unknown
- 2019-07-04 IL IL267853A patent/IL267853B/en active IP Right Grant
-
2020
- 2020-02-26 CY CY20201100177T patent/CY1122712T1/el unknown
- 2020-05-19 IL IL274771A patent/IL274771A/en unknown
- 2020-07-31 AU AU2020210278A patent/AU2020210278B2/en active Active
- 2020-10-07 JP JP2020169551A patent/JP7189185B2/ja active Active
-
2021
- 2021-06-13 IL IL283943A patent/IL283943B2/en unknown
- 2021-06-30 US US17/364,585 patent/US20220119393A1/en not_active Abandoned
- 2021-06-30 US US17/364,551 patent/US12152033B2/en active Active
- 2021-06-30 US US17/364,695 patent/US20210332059A1/en not_active Abandoned
-
2022
- 2022-08-16 AU AU2022218495A patent/AU2022218495B2/en active Active
- 2022-12-01 JP JP2022192954A patent/JP7556010B2/ja active Active
-
2024
- 2024-09-11 JP JP2024157116A patent/JP2025003975A/ja active Pending
- 2024-10-24 US US18/926,010 patent/US20250289823A1/en active Pending
- 2024-12-23 AU AU2024287194A patent/AU2024287194A1/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2016510035A5 (https=) | ||
| JP2017052805A5 (https=) | ||
| US11931363B2 (en) | Triazolopyrimidine compounds and uses thereof | |
| JP2019519484A5 (https=) | ||
| JP2010510319A5 (https=) | ||
| JP2018044008A5 (https=) | ||
| ME01507B (me) | Imidazotriazini i imidazopirimidini kao inhibitori kinaze | |
| JP2021502356A5 (https=) | ||
| JP2018527336A5 (https=) | ||
| RU2013155456A (ru) | Соединения пирролидинилмочевины и пирролидинилтиомочевины как ингибиторы киназы trka | |
| JP2017530999A5 (https=) | ||
| JP2017530185A5 (https=) | ||
| HRP20200263T1 (hr) | Upotreba derivata pirazolopirimidina za liječenje poremećaja povezanih sa pi3k | |
| JP2016523911A5 (https=) | ||
| JP2014511869A5 (https=) | ||
| RU2016136116A (ru) | Фармацевтические соединения | |
| JP2019504009A5 (https=) | ||
| RU2017124425A (ru) | Производные 2,4-диоксо-хиназолин-6-сульфонамида в качестве ингибиторов parg | |
| IL303196B2 (en) | Heteroaryl-substituted pyridines and methods of use | |
| RU2008138993A (ru) | Производные хинолина | |
| JP2017510554A5 (https=) | ||
| RU2017125520A (ru) | Соединения, ингибирующие parg | |
| WO2013006532A1 (en) | Combination therapy comprising a cdk4/6 inhibitor and a pi3k inhibitor for use in the treatment of cancer | |
| JP2012525349A5 (https=) | ||
| JP2015527401A5 (https=) |