JP2020517698A5 - - Google Patents
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- Publication number
- JP2020517698A5 JP2020517698A5 JP2019558390A JP2019558390A JP2020517698A5 JP 2020517698 A5 JP2020517698 A5 JP 2020517698A5 JP 2019558390 A JP2019558390 A JP 2019558390A JP 2019558390 A JP2019558390 A JP 2019558390A JP 2020517698 A5 JP2020517698 A5 JP 2020517698A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrido
- pyrimidin
- amine
- pyridine
- methyl
- 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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- 210000004027 cell Anatomy 0.000 claims description 303
- -1 R 0 Chemical group 0.000 claims description 246
- 150000001875 compounds Chemical class 0.000 claims description 198
- 238000000034 method Methods 0.000 claims description 193
- 125000000217 alkyl group Chemical group 0.000 claims description 173
- 229930186657 Lat Natural products 0.000 claims description 101
- 239000003202 long acting thyroid stimulator Substances 0.000 claims description 101
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 98
- 150000003839 salts Chemical class 0.000 claims description 80
- 125000001424 substituent group Chemical group 0.000 claims description 72
- 229910052736 halogen Inorganic materials 0.000 claims description 69
- 150000002367 halogens Chemical class 0.000 claims description 69
- 208000030533 eye disease Diseases 0.000 claims description 63
- 210000000130 stem cell Anatomy 0.000 claims description 61
- 125000005842 heteroatom Chemical group 0.000 claims description 60
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 52
- 241001430066 Anulocaulis Species 0.000 claims description 52
- 239000001257 hydrogen Substances 0.000 claims description 52
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 50
- 210000000399 corneal endothelial cell Anatomy 0.000 claims description 44
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 43
- 229910052757 nitrogen Inorganic materials 0.000 claims description 42
- MFGKTDNWDCJOLN-UHFFFAOYSA-N pyrido[3,4-d]pyrimidin-4-amine Chemical compound N1=CC=C2C(N)=NC=NC2=C1 MFGKTDNWDCJOLN-UHFFFAOYSA-N 0.000 claims description 42
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 37
- 208000035475 disorder Diseases 0.000 claims description 36
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 36
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 35
- 108090000623 proteins and genes Proteins 0.000 claims description 31
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- 229910052760 oxygen Inorganic materials 0.000 claims description 28
- 229910052717 sulfur Inorganic materials 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
- 238000012258 culturing Methods 0.000 claims description 25
- OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims description 24
- 150000002431 hydrogen Chemical class 0.000 claims description 22
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims description 20
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 19
- 239000001963 growth medium Substances 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 101000937544 Homo sapiens Beta-2-microglobulin Proteins 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 14
- 230000028993 immune response Effects 0.000 claims description 14
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 14
- 230000014509 gene expression Effects 0.000 claims description 13
- 230000001737 promoting effect Effects 0.000 claims description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 230000007812 deficiency Effects 0.000 claims description 12
- 238000012217 deletion Methods 0.000 claims description 12
- 230000037430 deletion Effects 0.000 claims description 12
- 238000003780 insertion Methods 0.000 claims description 12
- 230000037431 insertion Effects 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- 102100027314 Beta-2-microglobulin Human genes 0.000 claims description 11
- 102100028972 HLA class I histocompatibility antigen, A alpha chain Human genes 0.000 claims description 11
- 102100028976 HLA class I histocompatibility antigen, B alpha chain Human genes 0.000 claims description 11
- 102100028971 HLA class I histocompatibility antigen, C alpha chain Human genes 0.000 claims description 11
- 108010075704 HLA-A Antigens Proteins 0.000 claims description 11
- 108010058607 HLA-B Antigens Proteins 0.000 claims description 11
- 108010052199 HLA-C Antigens Proteins 0.000 claims description 11
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 10
- 230000002401 inhibitory effect Effects 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 125000002950 monocyclic group Chemical group 0.000 claims description 9
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 claims description 9
- 230000010261 cell growth Effects 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 8
- 235000019260 propionic acid Nutrition 0.000 claims description 8
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 238000012239 gene modification Methods 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- 150000002829 nitrogen Chemical class 0.000 claims description 7
- 150000007523 nucleic acids Chemical group 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 125000003367 polycyclic group Chemical group 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 claims description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- LISLXKHKNUTYFU-UHFFFAOYSA-N 2,2-dimethyl-N'-(2-pyridin-4-ylpyrido[3,4-d]pyrimidin-4-yl)propane-1,3-diamine Chemical compound CC(C)(CN)CNc1nc(nc2cnccc12)-c1ccncc1 LISLXKHKNUTYFU-UHFFFAOYSA-N 0.000 claims description 3
- MYPGOQOVEQKGDN-UHFFFAOYSA-N 2,3-dimethyl-3-N-(2-pyridin-4-ylpyrido[3,4-d]pyrimidin-4-yl)butane-2,3-diamine Chemical compound CC(C)(N)C(C)(C)Nc1nc(nc2cnccc12)-c1ccncc1 MYPGOQOVEQKGDN-UHFFFAOYSA-N 0.000 claims description 3
- CKGSKEKFMDASMJ-UHFFFAOYSA-N 2-methyl-2-N-(2-pyridin-4-ylpyrido[3,4-d]pyrimidin-4-yl)propane-1,2-diamine Chemical compound NCC(C)(C)NC=1C2=C(N=C(N=1)C1=CC=NC=C1)C=NC=C2 CKGSKEKFMDASMJ-UHFFFAOYSA-N 0.000 claims description 3
- ZKLQNSBYPMENKE-UHFFFAOYSA-N 3-N,2,2-trimethyl-1-N-(2-pyridin-4-ylpyrido[3,4-d]pyrimidin-4-yl)butane-1,3-diamine Chemical compound CC(C(CNC=1C2=C(N=C(N=1)C1=CC=NC=C1)C=NC=C2)(C)C)NC ZKLQNSBYPMENKE-UHFFFAOYSA-N 0.000 claims description 3
- PFJAMBGEYIVHBA-UHFFFAOYSA-N 5-chloro-N-(1-methylcyclopropyl)-2-pyridin-4-ylpyrido[3,4-d]pyrimidin-4-amine Chemical compound ClC1=CN=CC=2N=C(N=C(C=21)NC1(CC1)C)C1=CC=NC=C1 PFJAMBGEYIVHBA-UHFFFAOYSA-N 0.000 claims description 3
- RLWYFPYOBNIXQH-UHFFFAOYSA-N 8-chloro-N-(1-methylcyclopropyl)-2-pyridin-4-ylpyrido[3,4-d]pyrimidin-4-amine Chemical compound ClC1=NC=CC2=C1N=C(N=C2NC1(CC1)C)C1=CC=NC=C1 RLWYFPYOBNIXQH-UHFFFAOYSA-N 0.000 claims description 3
- NCURZWASYVOQOD-UHFFFAOYSA-N 8-methyl-N-(1-methylcyclopropyl)-2-pyridin-4-ylpyrido[3,4-d]pyrimidin-4-amine Chemical compound CC1=NC=CC2=C1N=C(N=C2NC1(CC1)C)C1=CC=NC=C1 NCURZWASYVOQOD-UHFFFAOYSA-N 0.000 claims description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 3
- CPJACQKXXLMUSC-UHFFFAOYSA-N N-tert-butyl-5-chloro-2-pyridin-4-ylpyrido[3,4-d]pyrimidin-4-amine Chemical compound C(C)(C)(C)NC=1C2=C(N=C(N=1)C1=CC=NC=C1)C=NC=C2Cl CPJACQKXXLMUSC-UHFFFAOYSA-N 0.000 claims description 3
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 3
- RGTXVXDNHPWPHH-UHFFFAOYSA-N butane-1,3-diamine Chemical compound CC(N)CCN RGTXVXDNHPWPHH-UHFFFAOYSA-N 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 239000007943 implant Substances 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- MSMNYSIKXYTNCQ-SJLPKXTDSA-N (1R,2R)-1-N,2-N-dimethyl-2-N-(2-pyridin-4-ylpyrido[3,4-d]pyrimidin-4-yl)cyclohexane-1,2-diamine Chemical compound CN([C@H]1[C@@H](CCCC1)NC)C=1C2=C(N=C(N=1)C1=CC=NC=C1)C=NC=C2 MSMNYSIKXYTNCQ-SJLPKXTDSA-N 0.000 claims description 2
- KLRVBQBFDCULDA-DZGCQCFKSA-N (1R,2S)-2-[(2-pyridin-4-ylpyrido[3,4-d]pyrimidin-4-yl)amino]cyclopentan-1-ol Chemical compound O[C@@H]1CCC[C@@H]1Nc1nc(nc2cnccc12)-c1ccncc1 KLRVBQBFDCULDA-DZGCQCFKSA-N 0.000 claims description 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
- ASGAQYCHHHOJMV-UHFFFAOYSA-N 1-[2-[[2-(3-chloropyridin-4-yl)pyrido[3,4-d]pyrimidin-4-yl]amino]-2-methylpropoxy]-2-methylpropan-2-ol Chemical compound ClC=1C=NC=CC=1C=1N=C(C2=C(N=1)C=NC=C2)NC(COCC(C)(O)C)(C)C ASGAQYCHHHOJMV-UHFFFAOYSA-N 0.000 claims description 2
- RQCQSMAAAMSVHQ-UHFFFAOYSA-N 2,4-dimethyl-4-[(2-pyridin-4-ylpyrido[3,4-d]pyrimidin-4-yl)amino]pentan-2-ol Chemical compound CC(C)(CC(C)(NC=1C2=C(N=C(N=1)C1=CC=NC=C1)C=NC=C2)C)O RQCQSMAAAMSVHQ-UHFFFAOYSA-N 0.000 claims description 2
- LCMHVCYOECYAMC-UHFFFAOYSA-N 2,4-dimethyl-4-[[2-(1H-pyrazol-4-yl)pyrido[3,4-d]pyrimidin-4-yl]amino]pentan-2-ol Chemical compound CC(C)(CC(C)(NC=1C2=C(N=C(N=1)C=1C=NNC=1)C=NC=C2)C)O LCMHVCYOECYAMC-UHFFFAOYSA-N 0.000 claims description 2
- XFAFYUWFKMLDGN-UHFFFAOYSA-N 2,4-dimethyl-4-[[2-[5-(trifluoromethyl)-1H-pyrazol-4-yl]pyrido[3,4-d]pyrimidin-4-yl]amino]pentan-2-ol Chemical compound CC(C)(CC(C)(NC=1C2=C(N=C(N=1)C=1C(=NNC=1)C(F)(F)F)C=NC=C2)C)O XFAFYUWFKMLDGN-UHFFFAOYSA-N 0.000 claims description 2
- FGUYUDSFYMXCSF-UHFFFAOYSA-N 2-(1,1,1-trifluoro-2-methylpropan-2-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound FC(C(C)(C)C=1N=C(C2=C(N=1)C=NC=C2)N)(F)F FGUYUDSFYMXCSF-UHFFFAOYSA-N 0.000 claims description 2
- AJBBECKCWREWAW-UHFFFAOYSA-N 2-(2-aminopyridin-4-yl)-N-(1-methylcyclopropyl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound CC1(CC1)NC=1C2=C(N=C(N=1)C1=CC(=NC=C1)N)C=NC=C2 AJBBECKCWREWAW-UHFFFAOYSA-N 0.000 claims description 2
- IJGJWWBUSDGYNE-UHFFFAOYSA-N 2-(2-methylpyrazol-3-yl)-N-(1-pyridin-4-ylethyl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound CN1N=CC=C1C=1N=C(C2=C(N=1)C=NC=C2)NC(C)C1=CC=NC=C1 IJGJWWBUSDGYNE-UHFFFAOYSA-N 0.000 claims description 2
- GPKFECYSQTWZCI-UHFFFAOYSA-N 2-(3-chloropyridin-4-yl)-N-(1,1,1-trifluoro-2-methylpropan-2-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound ClC=1C=NC=CC=1C=1N=C(C2=C(N=1)C=NC=C2)NC(C(F)(F)F)(C)C GPKFECYSQTWZCI-UHFFFAOYSA-N 0.000 claims description 2
- OXIMJDPCKQGAMC-UHFFFAOYSA-N 2-(3-chloropyridin-4-yl)-N-(2-methylbutan-2-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound ClC=1C=NC=CC=1C=1N=C(C2=C(N=1)C=NC=C2)NC(C)(CC)C OXIMJDPCKQGAMC-UHFFFAOYSA-N 0.000 claims description 2
- NWTRZYRGCGNAAN-SECBINFHSA-N 2-(3-fluoropyridin-4-yl)-N-methyl-N-[(2R)-1,1,1-trifluoropropan-2-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound FC=1C=NC=CC=1C=1N=C(C2=C(N=1)C=NC=C2)N([C@@H](C(F)(F)F)C)C NWTRZYRGCGNAAN-SECBINFHSA-N 0.000 claims description 2
- VBBQTFSHBKUYOD-UHFFFAOYSA-N 2-(3-fluoropyridin-4-yl)-N-methyl-N-propan-2-ylpyrido[3,4-d]pyrimidin-4-amine Chemical compound FC=1C=NC=CC=1C=1N=C(C2=C(N=1)C=NC=C2)N(C(C)C)C VBBQTFSHBKUYOD-UHFFFAOYSA-N 0.000 claims description 2
- CCJRVCDZHWNBTA-UHFFFAOYSA-N 2-(5-methyl-1H-pyrazol-4-yl)-N-(1,1,1-trifluoro-2-methylpropan-2-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound CC1=NNC=C1C=1N=C(C2=C(N=1)C=NC=C2)NC(C(F)(F)F)(C)C CCJRVCDZHWNBTA-UHFFFAOYSA-N 0.000 claims description 2
- ZOBZTNONBIVPBE-UHFFFAOYSA-N 2-(hydroxymethyl)-2-[(2-pyridin-4-ylpyrido[3,4-d]pyrimidin-4-yl)amino]propane-1,3-diol Chemical compound OCC(CO)(CO)NC=1C2=C(N=C(N=1)C1=CC=NC=C1)C=NC=C2 ZOBZTNONBIVPBE-UHFFFAOYSA-N 0.000 claims description 2
- JVCDXTHYVYGMQC-UHFFFAOYSA-N 2-[2-methyl-2-[(2-pyridin-4-ylpyrido[3,4-d]pyrimidin-4-yl)amino]propoxy]ethanol Chemical compound CC(COCCO)(C)NC=1C2=C(N=C(N=1)C1=CC=NC=C1)C=NC=C2 JVCDXTHYVYGMQC-UHFFFAOYSA-N 0.000 claims description 2
- KTRVKZXQBVEQBL-UHFFFAOYSA-N 2-methyl-2-N-[2-(1H-pyrazol-4-yl)pyrido[3,4-d]pyrimidin-4-yl]propane-1,2-diamine Chemical compound NCC(C)(C)NC=1C2=C(N=C(N=1)C=1C=NNC=1)C=NC=C2 KTRVKZXQBVEQBL-UHFFFAOYSA-N 0.000 claims description 2
- DCIPFXLSLUFVQA-UHFFFAOYSA-N 2-methyl-2-[(2-pyridin-4-ylpyrido[3,4-d]pyrimidin-4-yl)amino]propan-1-ol Chemical compound CC(CO)(C)NC=1C2=C(N=C(N=1)C1=CC=NC=C1)C=NC=C2 DCIPFXLSLUFVQA-UHFFFAOYSA-N 0.000 claims description 2
- GASZFPAPBAGRFK-UHFFFAOYSA-N 2-methyl-2-[(2-pyridin-4-ylpyrido[3,4-d]pyrimidin-4-yl)amino]propane-1,3-diol Chemical compound CC(CO)(CO)NC=1C2=C(N=C(N=1)C1=CC=NC=C1)C=NC=C2 GASZFPAPBAGRFK-UHFFFAOYSA-N 0.000 claims description 2
- YSXUPBSDPJABHI-UHFFFAOYSA-N 2-methyl-4-N-(2-pyridin-4-ylpyrido[3,4-d]pyrimidin-4-yl)pentane-2,4-diamine Chemical compound CC(CC(C)(N)C)NC=1C2=C(N=C(N=1)C1=CC=NC=C1)C=NC=C2 YSXUPBSDPJABHI-UHFFFAOYSA-N 0.000 claims description 2
- JYVLIDXNZAXMDK-UHFFFAOYSA-N 2-pentanol Substances CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 claims description 2
- NCWUWMQIMGPXQR-AWEZNQCLSA-N 2-pyridin-4-yl-4-[(3S)-3-(trifluoromethyl)piperazin-1-yl]pyrido[3,4-d]pyrimidine Chemical compound N1=CC=C(C=C1)C=1N=C(C2=C(N=1)C=NC=C2)N1C[C@H](NCC1)C(F)(F)F NCWUWMQIMGPXQR-AWEZNQCLSA-N 0.000 claims description 2
- PTTKHXBEPPAXSE-UHFFFAOYSA-N 2-pyridin-4-yl-N-(1,1,1-trifluoropropan-2-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound N1=CC=C(C=C1)C=1N=C(C2=C(N=1)C=NC=C2)NC(C(F)(F)F)C PTTKHXBEPPAXSE-UHFFFAOYSA-N 0.000 claims description 2
- RGIKJUZEMMTILQ-UHFFFAOYSA-N 2-pyridin-4-yl-N-[1-(trifluoromethyl)cyclobutyl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound N1=CC=C(C=C1)C=1N=C(C2=C(N=1)C=NC=C2)NC1(CCC1)C(F)(F)F RGIKJUZEMMTILQ-UHFFFAOYSA-N 0.000 claims description 2
- ACTDLFQRJKPKFQ-UHFFFAOYSA-N 2-pyridin-4-yl-N-[1-(trifluoromethyl)cyclopropyl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound N1=CC=C(C=C1)C=1N=C(C2=C(N=1)C=NC=C2)NC1(CC1)C(F)(F)F ACTDLFQRJKPKFQ-UHFFFAOYSA-N 0.000 claims description 2
- GSYJHCKYYPELPH-UHFFFAOYSA-N 2-pyridin-4-yl-N-[3-(2H-tetrazol-5-yl)propyl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound N1=CC=C(C=C1)C=1N=C(C2=C(N=1)C=NC=C2)NCCCC1=NN=NN1 GSYJHCKYYPELPH-UHFFFAOYSA-N 0.000 claims description 2
- PEYNBYLLSKMKNU-UHFFFAOYSA-N 2-pyridin-4-ylpyrido[3,4-d]pyrimidin-4-amine Chemical compound N=1C2=CN=CC=C2C(N)=NC=1C1=CC=NC=C1 PEYNBYLLSKMKNU-UHFFFAOYSA-N 0.000 claims description 2
- STAZQQYFJAXCJL-UHFFFAOYSA-N 2-pyridin-4-ylpyrido[3,4-d]pyrimidine Chemical compound C1=NC=CC(C=2N=C3C=NC=CC3=CN=2)=C1 STAZQQYFJAXCJL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- KSQYPFHEXAQSRA-UHFFFAOYSA-N 4-N,2-dimethyl-2-N-[2-[5-(trifluoromethyl)-1H-pyrazol-4-yl]pyrido[3,4-d]pyrimidin-4-yl]pentane-2,4-diamine Chemical compound CC(CC(C)(NC=1C2=C(N=C(N=1)C=1C(=NNC=1)C(F)(F)F)C=NC=C2)C)NC KSQYPFHEXAQSRA-UHFFFAOYSA-N 0.000 claims description 2
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| TW202005643A (zh) | 2018-06-08 | 2020-02-01 | 日商日產化學股份有限公司 | 激酶抑制劑 |
| HRP20250676T1 (hr) | 2018-06-29 | 2025-08-01 | Incyte Corporation | Formulacije inhibitora axl/mer |
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