JP2020503271A5 - - Google Patents
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- JP2020503271A5 JP2020503271A5 JP2019528807A JP2019528807A JP2020503271A5 JP 2020503271 A5 JP2020503271 A5 JP 2020503271A5 JP 2019528807 A JP2019528807 A JP 2019528807A JP 2019528807 A JP2019528807 A JP 2019528807A JP 2020503271 A5 JP2020503271 A5 JP 2020503271A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- compound according
- chloro
- phenyl
- methoxy
- 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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- 150000001875 compounds Chemical class 0.000 claims description 129
- 125000000217 alkyl group Chemical group 0.000 claims description 81
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 41
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 40
- 229910052736 halogen Inorganic materials 0.000 claims description 40
- 150000002367 halogens Chemical class 0.000 claims description 40
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 38
- 229910052799 carbon Inorganic materials 0.000 claims description 34
- -1 and Chemical group 0.000 claims description 33
- 125000003545 alkoxy group Chemical group 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 31
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 22
- WQAWEUZTDVWTDB-UHFFFAOYSA-N dimethyl(oxo)phosphanium Chemical compound C[P+](C)=O WQAWEUZTDVWTDB-UHFFFAOYSA-N 0.000 claims description 19
- 229910052805 deuterium Inorganic materials 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 8
- 101001059991 Homo sapiens Mitogen-activated protein kinase kinase kinase kinase 1 Proteins 0.000 claims description 8
- 102100028199 Mitogen-activated protein kinase kinase kinase kinase 1 Human genes 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000000651 prodrug Substances 0.000 claims description 8
- 229940002612 prodrug Drugs 0.000 claims description 8
- 239000012453 solvate Substances 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 7
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 6
- 208000035475 disorder Diseases 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 230000001404 mediated effect Effects 0.000 claims description 6
- 125000004043 oxo group Chemical group O=* 0.000 claims description 6
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 206010061218 Inflammation Diseases 0.000 claims description 3
- 206010027476 Metastases Diseases 0.000 claims description 3
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 230000001363 autoimmune Effects 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 230000004054 inflammatory process Effects 0.000 claims description 3
- 230000009401 metastasis Effects 0.000 claims description 3
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 2
- KDXVHFUSESBPAJ-UHFFFAOYSA-N 2-N-(5-bromo-2-methyl-3,4-dihydro-1H-isoquinolin-7-yl)-5-chloro-4-N-(2-dimethylphosphorylphenyl)pyrimidine-2,4-diamine Chemical compound CN1CCC2=C(C1)C=C(NC1=NC(NC3=C(C=CC=C3)P(C)(C)=O)=C(Cl)C=N1)C=C2Br KDXVHFUSESBPAJ-UHFFFAOYSA-N 0.000 claims description 2
- WSWVNNMGZOPQPJ-UHFFFAOYSA-N 2-[[5-chloro-2-[(6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-yl)amino]pyrimidin-4-yl]amino]-N,N-dimethylbenzenesulfonamide Chemical compound COC1=CC2=C(CN(C)CC2)C=C1NC1=NC(NC2=C(C=CC=C2)S(=O)(=O)N(C)C)=C(Cl)C=N1 WSWVNNMGZOPQPJ-UHFFFAOYSA-N 0.000 claims description 2
- DSIDJCGDDHITGX-UHFFFAOYSA-N 2-[[5-chloro-2-[(6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-yl)amino]pyrimidin-4-yl]amino]-N-methylbenzamide Chemical compound CNC(=O)C1=C(NC2=C(Cl)C=NC(NC3=CC4=C(CCN(C)C4)C=C3OC)=N2)C=CC=C1 DSIDJCGDDHITGX-UHFFFAOYSA-N 0.000 claims description 2
- ZXCLJAYBOJECIX-UHFFFAOYSA-N 4-N-(2-dimethylphosphorylphenyl)-2-N-(6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-yl)-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound COC1=CC2=C(CN(C)CC2)C=C1NC1=NC(NC2=C(C=CC=C2)P(C)(C)=O)=C(C=N1)C(F)(F)F ZXCLJAYBOJECIX-UHFFFAOYSA-N 0.000 claims description 2
- FQPWWXCVRKPESV-UHFFFAOYSA-N 4-N-(2-dimethylphosphorylphenyl)-5-ethenyl-2-N-(6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-yl)pyrimidine-2,4-diamine Chemical compound COC=1C=C2CCN(CC2=CC=1NC1=NC=C(C(=N1)NC1=C(C=CC=C1)P(C)(C)=O)C=C)C FQPWWXCVRKPESV-UHFFFAOYSA-N 0.000 claims description 2
- KMGVAIZSYSAYER-UHFFFAOYSA-N 4-N-(2-dimethylphosphorylphenyl)-5-fluoro-2-N-(6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-yl)pyrimidine-2,4-diamine Chemical compound COC1=CC2=C(CN(C)CC2)C=C1NC1=NC(NC2=C(C=CC=C2)P(C)(C)=O)=C(F)C=N1 KMGVAIZSYSAYER-UHFFFAOYSA-N 0.000 claims description 2
- VWQWFOYWQBTTRH-UHFFFAOYSA-N 4-N-(2-dimethylphosphorylphenyl)-5-methoxy-2-N-(6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-yl)pyrimidine-2,4-diamine Chemical compound COc1cc2CCN(C)Cc2cc1Nc1ncc(OC)c(Nc2ccccc2P(C)(C)=O)n1 VWQWFOYWQBTTRH-UHFFFAOYSA-N 0.000 claims description 2
- KCALPMNDTLQRTH-UHFFFAOYSA-N 5-bromo-4-N-(2-dimethylphosphorylphenyl)-2-N-(6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-yl)pyrimidine-2,4-diamine Chemical compound COC1=CC2=C(CN(C)CC2)C=C1NC1=NC(NC2=C(C=CC=C2)P(C)(C)=O)=C(Br)C=N1 KCALPMNDTLQRTH-UHFFFAOYSA-N 0.000 claims description 2
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims description 2
- JWZUKVXRKDHRBL-XUWBISKJSA-N 5-chloro-2-N-(1,1-dideuterio-6-methoxy-3,4-dihydro-2H-isoquinolin-7-yl)-4-N-(2-dimethylphosphorylphenyl)pyrimidine-2,4-diamine Chemical compound ClC=1C(=NC(=NC=1)NC1=C(C=C2CCNC(C2=C1)([2H])[2H])OC)NC1=C(C=CC=C1)P(C)(C)=O JWZUKVXRKDHRBL-XUWBISKJSA-N 0.000 claims description 2
- QKUPFBJAQPFYLF-UHFFFAOYSA-N 5-chloro-2-N-(6-chloro-2-methyl-3,4-dihydro-1H-isoquinolin-7-yl)-4-N-(2-diethylphosphorylphenyl)pyrimidine-2,4-diamine Chemical compound ClC=1C(=NC(=NC=1)NC1=C(C=C2CCN(CC2=C1)C)Cl)NC1=C(C=CC=C1)P(CC)(CC)=O QKUPFBJAQPFYLF-UHFFFAOYSA-N 0.000 claims description 2
- YDGQSMDKANRAGC-UHFFFAOYSA-N 5-chloro-2-N-(6-chloro-2-methyl-3,4-dihydro-1H-isoquinolin-7-yl)-4-N-(2-dimethylphosphorylphenyl)pyrimidine-2,4-diamine Chemical compound CN1CCC2=CC(Cl)=C(NC3=NC=C(Cl)C(NC4=CC=CC=C4P(C)(C)=O)=N3)C=C2C1 YDGQSMDKANRAGC-UHFFFAOYSA-N 0.000 claims description 2
- NALCFIMWIMQFHB-UHFFFAOYSA-N 5-chloro-2-N-(7-chloro-2-methyl-3,4-dihydro-1H-isoquinolin-6-yl)-4-N-(2-dimethylphosphorylphenyl)pyrimidine-2,4-diamine Chemical compound CN1CCc2cc(Nc3ncc(Cl)c(Nc4ccccc4P(C)(C)=O)n3)c(Cl)cc2C1 NALCFIMWIMQFHB-UHFFFAOYSA-N 0.000 claims description 2
- QZQVFEBSSZKRST-UHFFFAOYSA-N 5-chloro-2-N-[2-(dimethylamino)-6-methoxy-2,3-dihydro-1H-inden-5-yl]-4-N-(2-dimethylphosphorylphenyl)pyrimidine-2,4-diamine Chemical compound ClC=1C(=NC(=NC=1)NC=1C=C2CC(CC2=CC=1OC)N(C)C)NC1=C(C=CC=C1)P(C)(C)=O QZQVFEBSSZKRST-UHFFFAOYSA-N 0.000 claims description 2
- PCQCOJFILICLRG-UHFFFAOYSA-N 5-chloro-4-N-(2-diethylphosphorylphenyl)-2-N-(6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-yl)pyrimidine-2,4-diamine Chemical compound ClC=1C(=NC(=NC=1)NC1=C(C=C2CCN(CC2=C1)C)OC)NC1=C(C=CC=C1)P(CC)(CC)=O PCQCOJFILICLRG-UHFFFAOYSA-N 0.000 claims description 2
- HVDMUQVAANCBIM-UHFFFAOYSA-N 5-chloro-4-N-(2-dimethylphosphorylphenyl)-2-N-(6-ethenyl-2-methyl-3,4-dihydro-1H-isoquinolin-7-yl)pyrimidine-2,4-diamine Chemical compound ClC=1C(=NC(=NC=1)NC1=C(C=C2CCN(CC2=C1)C)C=C)NC1=C(C=CC=C1)P(=O)(C)C HVDMUQVAANCBIM-UHFFFAOYSA-N 0.000 claims description 2
- OEJBKISZXAVCHL-UHFFFAOYSA-N 5-chloro-4-N-(2-dimethylphosphorylphenyl)-2-N-(6-ethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-yl)pyrimidine-2,4-diamine Chemical compound ClC=1C(=NC(=NC=1)NC1=C(C=C2CCN(CC2=C1)C)OCC)NC1=C(C=CC=C1)P(C)(C)=O OEJBKISZXAVCHL-UHFFFAOYSA-N 0.000 claims description 2
- SWYNJFAPAFZRMF-UHFFFAOYSA-N 5-chloro-4-N-(2-dimethylphosphorylphenyl)-2-N-(6-ethyl-2-methyl-3,4-dihydro-1H-isoquinolin-7-yl)pyrimidine-2,4-diamine Chemical compound ClC=1C(=NC(=NC=1)NC1=C(C=C2CCN(CC2=C1)C)CC)NC1=C(C=CC=C1)P(=O)(C)C SWYNJFAPAFZRMF-UHFFFAOYSA-N 0.000 claims description 2
- ZSAIMPBXGWCIEV-UHFFFAOYSA-N 5-chloro-4-N-(2-dimethylphosphorylphenyl)-2-N-(6-fluoro-2-methyl-3,4-dihydro-1H-isoquinolin-7-yl)pyrimidine-2,4-diamine Chemical compound CN1CCC2=C(C1)C=C(NC1=NC(NC3=C(C=CC=C3)P(C)(C)=O)=C(Cl)C=N1)C(F)=C2 ZSAIMPBXGWCIEV-UHFFFAOYSA-N 0.000 claims description 2
- FLCNVWSKXSRARI-UHFFFAOYSA-N 5-chloro-4-N-(2-dimethylphosphorylphenyl)-2-N-(6-methoxy-1,1,2-trimethyl-3,4-dihydroisoquinolin-7-yl)pyrimidine-2,4-diamine Chemical compound ClC=1C(=NC(=NC=1)NC1=C(C=C2CCN(C(C2=C1)(C)C)C)OC)NC1=C(C=CC=C1)P(C)(C)=O FLCNVWSKXSRARI-UHFFFAOYSA-N 0.000 claims description 2
- JWZUKVXRKDHRBL-UHFFFAOYSA-N 5-chloro-4-N-(2-dimethylphosphorylphenyl)-2-N-(6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-yl)pyrimidine-2,4-diamine Chemical compound COC1=CC2=C(CNCC2)C=C1NC1=NC(NC2=C(C=CC=C2)P(C)(C)=O)=C(Cl)C=N1 JWZUKVXRKDHRBL-UHFFFAOYSA-N 0.000 claims description 2
- ZIIMDSSVIOLWDT-UHFFFAOYSA-N 5-chloro-4-N-(2-dimethylphosphorylphenyl)-2-N-(6-methoxy-1,2-dimethyl-3,4-dihydro-1H-isoquinolin-7-yl)pyrimidine-2,4-diamine Chemical compound COC1=CC2=C(C=C1NC1=NC(NC3=C(C=CC=C3)P(C)(C)=O)=C(Cl)C=N1)C(C)N(C)CC2 ZIIMDSSVIOLWDT-UHFFFAOYSA-N 0.000 claims description 2
- CFYLJYBFMCKWRT-UHFFFAOYSA-N 5-chloro-4-N-(2-dimethylphosphorylphenyl)-2-N-(6-methoxy-2,4,4-trimethyl-1,3-dihydroisoquinolin-7-yl)pyrimidine-2,4-diamine Chemical compound COC1=CC2=C(CN(C)CC2(C)C)C=C1NC1=NC(NC2=C(C=CC=C2)P(C)(C)=O)=C(Cl)C=N1 CFYLJYBFMCKWRT-UHFFFAOYSA-N 0.000 claims description 2
- PKCVIEAEQWBROQ-UHFFFAOYSA-N 5-chloro-4-N-(2-dimethylphosphorylphenyl)-2-N-(6-methoxy-2-methyl-1,3-dihydroisoindol-5-yl)pyrimidine-2,4-diamine Chemical compound ClC=1C(=NC(=NC=1)NC=1C=C2CN(CC2=CC=1OC)C)NC1=C(C=CC=C1)P(C)(C)=O PKCVIEAEQWBROQ-UHFFFAOYSA-N 0.000 claims description 2
- QWCVGHXDHVKGAQ-UHFFFAOYSA-N 5-chloro-4-N-(2-dimethylphosphorylphenyl)-2-N-(6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-yl)pyrimidine-2,4-diamine Chemical compound COC1=CC2=C(CN(C)CC2)C=C1NC1=NC(NC2=C(C=CC=C2)P(C)(C)=O)=C(Cl)C=N1 QWCVGHXDHVKGAQ-UHFFFAOYSA-N 0.000 claims description 2
- NFCFFFWUBSUWNP-UHFFFAOYSA-N 5-chloro-4-N-(2-dimethylphosphorylphenyl)-2-N-(6-methoxy-2-propan-2-yl-3,4-dihydro-1H-isoquinolin-7-yl)pyrimidine-2,4-diamine Chemical compound COC1=CC2=C(CN(CC2)C(C)C)C=C1NC1=NC(NC2=C(C=CC=C2)P(C)(C)=O)=C(Cl)C=N1 NFCFFFWUBSUWNP-UHFFFAOYSA-N 0.000 claims description 2
- GLJAYMYZSWMKMI-UHFFFAOYSA-N 5-chloro-4-N-(2-dimethylphosphorylphenyl)-2-N-(6-methoxy-4,4-dimethyl-2,3-dihydro-1H-isoquinolin-7-yl)pyrimidine-2,4-diamine Chemical compound COC1=CC2=C(CNCC2(C)C)C=C1NC1=NC(NC2=C(C=CC=C2)P(C)(C)=O)=C(Cl)C=N1 GLJAYMYZSWMKMI-UHFFFAOYSA-N 0.000 claims description 2
- PUWIWAQYKIBXFP-UHFFFAOYSA-N 5-chloro-4-N-(2-dimethylphosphorylphenyl)-2-N-(7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-yl)pyrimidine-2,4-diamine Chemical compound COC1=CC2=C(CCNC2)C=C1NC1=NC(NC2=C(C=CC=C2)P(C)(C)=O)=C(Cl)C=N1 PUWIWAQYKIBXFP-UHFFFAOYSA-N 0.000 claims description 2
- BUGDBYWBQSINKL-UHFFFAOYSA-N 5-chloro-4-N-(2-dimethylphosphorylphenyl)-2-N-(7-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-6-yl)pyrimidine-2,4-diamine Chemical compound ClC=1C(=NC(=NC=1)NC=1C=C2CCN(CC2=CC=1OC)C)NC1=C(C=CC=C1)P(C)(C)=O BUGDBYWBQSINKL-UHFFFAOYSA-N 0.000 claims description 2
- LXNIIMDKSBVIPM-UHFFFAOYSA-N 5-chloro-4-N-(2-dimethylphosphorylphenyl)-2-N-(9-methoxy-2,3,4,6,11,11a-hexahydro-1H-benzo[b]quinolizin-8-yl)pyrimidine-2,4-diamine Chemical compound ClC=1C(=NC(=NC=1)NC1=CC2=C(CC3CCCCN3C2)C=C1OC)NC1=C(C=CC=C1)P(=O)(C)C LXNIIMDKSBVIPM-UHFFFAOYSA-N 0.000 claims description 2
- DFAKEQRUAJGWMX-UHFFFAOYSA-N 5-chloro-4-N-(2-dimethylphosphorylphenyl)-2-N-[6-(trifluoromethyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]pyrimidine-2,4-diamine Chemical compound CP(C)(=O)C1=C(NC2=C(Cl)C=NC(NC3=CC4=C(CCNC4)C=C3C(F)(F)F)=N2)C=CC=C1 DFAKEQRUAJGWMX-UHFFFAOYSA-N 0.000 claims description 2
- XEUXLBPKFACCHV-UHFFFAOYSA-N 5-chloro-4-N-(2-dimethylphosphorylphenyl)-2-N-[6-methoxy-2-(oxetan-3-yl)-3,4-dihydro-1H-isoquinolin-7-yl]pyrimidine-2,4-diamine Chemical compound COC1=CC2=C(CN(CC2)C2COC2)C=C1NC1=NC(NC2=C(C=CC=C2)P(C)(C)=O)=C(Cl)C=N1 XEUXLBPKFACCHV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000004437 phosphorous atom Chemical group 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical compound NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 7
- CORHJJNVWGMXIV-UHFFFAOYSA-N 8-[[5-chloro-4-(2-dimethylphosphorylanilino)pyrimidin-2-yl]amino]-7-methoxy-2-methyl-4,5-dihydro-3H-2-benzazepin-1-one Chemical compound ClC=1C(=NC(=NC=1)NC=1C(=CC2=C(C(N(CCC2)C)=O)C=1)OC)NC1=C(C=CC=C1)P(=O)(C)C CORHJJNVWGMXIV-UHFFFAOYSA-N 0.000 claims 1
- HGDIHUZVQPKSMO-UHFFFAOYSA-N methylphosphonoylmethane Chemical compound CP(C)=O HGDIHUZVQPKSMO-UHFFFAOYSA-N 0.000 claims 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 1
- 238000000034 method Methods 0.000 description 8
- 0 *C1(*)c2cc(Nc3ncc(*)c(Nc4c(*)cccc4)n3)c(*)cc2*CC*1 Chemical compound *C1(*)c2cc(Nc3ncc(*)c(Nc4c(*)cccc4)n3)c(*)cc2*CC*1 0.000 description 3
- BRXHMPPDBUOUQS-UHFFFAOYSA-N 4-N-(2-dimethylphosphorylphenyl)-2-N-(6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-yl)pyrimidine-2,4-diamine Chemical compound COC1=CC2=C(CN(C)CC2)C=C1NC1=NC(NC2=C(C=CC=C2)P(C)(C)=O)=CC=N1 BRXHMPPDBUOUQS-UHFFFAOYSA-N 0.000 description 1
- YXJNHAGAOHGMPU-UHFFFAOYSA-N CCC1=CN=C(NC(C=C(CN(C)CC2)C2=C2)=C2OC)N=C1NC(C=CC=C1)=C1P(C)C Chemical compound CCC1=CN=C(NC(C=C(CN(C)CC2)C2=C2)=C2OC)N=C1NC(C=CC=C1)=C1P(C)C YXJNHAGAOHGMPU-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 208000037765 diseases and disorders Diseases 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662428191P | 2016-11-30 | 2016-11-30 | |
| US62/428,191 | 2016-11-30 | ||
| PCT/US2017/063633 WO2018102366A1 (en) | 2016-11-30 | 2017-11-29 | Anilinopyrimidines as haematopoietic progenitor kinase 1 (hpk1) inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020503271A JP2020503271A (ja) | 2020-01-30 |
| JP2020503271A5 true JP2020503271A5 (OSRAM) | 2021-01-07 |
| JP7025426B2 JP7025426B2 (ja) | 2022-02-24 |
Family
ID=60629854
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019528807A Active JP7025426B2 (ja) | 2016-11-30 | 2017-11-29 | 造血前駆体キナーゼ１（ｈｐｋ１）阻害剤としてのアニリノピリミジンａｓ |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US11180482B2 (OSRAM) |
| EP (1) | EP3548479A1 (OSRAM) |
| JP (1) | JP7025426B2 (OSRAM) |
| MA (1) | MA46942A (OSRAM) |
| WO (1) | WO2018102366A1 (OSRAM) |
Families Citing this family (83)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MA48994A (fr) | 2017-03-30 | 2020-02-05 | Hoffmann La Roche | Isoquinoléines utilisées en tant qu'inhibiteurs de hpk1 |
| JP7167146B2 (ja) | 2017-11-06 | 2022-11-08 | ブリストル－マイヤーズ スクイブ カンパニー | Ｈｐｋ１阻害剤として有用なイソフラノン化合物 |
| TW202012405A (zh) * | 2018-07-24 | 2020-04-01 | 瑞士商赫孚孟拉羅股份公司 | 萘啶化合物及其用途 |
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- 2017-11-29 US US16/465,073 patent/US11180482B2/en active Active
- 2017-11-29 MA MA046942A patent/MA46942A/fr unknown
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