JP2018522852A5 - - Google Patents
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- JP2018522852A5 JP2018522852A5 JP2017565779A JP2017565779A JP2018522852A5 JP 2018522852 A5 JP2018522852 A5 JP 2018522852A5 JP 2017565779 A JP2017565779 A JP 2017565779A JP 2017565779 A JP2017565779 A JP 2017565779A JP 2018522852 A5 JP2018522852 A5 JP 2018522852A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- oxo
- chloro
- pyrimidin
- ethyl
- 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 77
- 239000000126 substance Substances 0.000 claims description 76
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 229910052736 halogen Inorganic materials 0.000 claims description 32
- 150000002367 halogens Chemical class 0.000 claims description 28
- 125000004429 atom Chemical group 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
- 125000005842 heteroatom Chemical group 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 150000002431 hydrogen Chemical group 0.000 claims description 14
- 230000003287 optical effect Effects 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims 19
- UDJFFSGCRRMVFH-UHFFFAOYSA-N pyrido[2,3-d]pyrimidine Chemical compound N1=CN=CC2=CC=CN=C21 UDJFFSGCRRMVFH-UHFFFAOYSA-N 0.000 claims 14
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 claims 6
- 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 claims 6
- UKAFWJUARMVPPH-UHFFFAOYSA-N 8h-pyrimido[4,5-d]pyrimidin-5-one Chemical compound C1=NC=C2C(=O)N=CNC2=N1 UKAFWJUARMVPPH-UHFFFAOYSA-N 0.000 claims 5
- 125000006242 amine protecting group Chemical group 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- -1 t-butyloxycarbonyl Chemical group 0.000 claims 5
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 230000001225 therapeutic effect Effects 0.000 claims 4
- 208000023275 Autoimmune disease Diseases 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 230000002378 acidificating effect Effects 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 230000003449 preventive effect Effects 0.000 claims 3
- QGDYVSSVBYMOJN-UHFFFAOYSA-N pyrimido[4,5-d]pyrimidine Chemical compound C1=NC=NC2=NC=NC=C21 QGDYVSSVBYMOJN-UHFFFAOYSA-N 0.000 claims 3
- 208000023504 respiratory system disease Diseases 0.000 claims 3
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims 2
- 206010009944 Colon cancer Diseases 0.000 claims 2
- 206010035664 Pneumonia Diseases 0.000 claims 2
- 208000021386 Sjogren Syndrome Diseases 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 2
- 208000029742 colonic neoplasm Diseases 0.000 claims 2
- 235000013376 functional food Nutrition 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 claims 1
- LJCZNYWLQZZIOS-UHFFFAOYSA-N 2,2,2-trichlorethoxycarbonyl chloride Chemical compound ClC(=O)OCC(Cl)(Cl)Cl LJCZNYWLQZZIOS-UHFFFAOYSA-N 0.000 claims 1
- UROFNPHOYZVMMN-UHFFFAOYSA-N 2-amino-4-[1-(5-chloro-4-oxo-3-phenylquinazolin-2-yl)ethylamino]-6-methyl-7,8-dihydropyrimido[4,5-d]pyrimidin-5-one Chemical compound NC1=NC(=C2C(=N1)NCN(C2=O)C)NC(C)C1=NC2=CC=CC(=C2C(N1C1=CC=CC=C1)=O)Cl UROFNPHOYZVMMN-UHFFFAOYSA-N 0.000 claims 1
- NSAGXRGAZQJOFN-UHFFFAOYSA-N 2-amino-4-[1-(5-chloro-4-oxo-3-pyridin-3-ylquinazolin-2-yl)ethylamino]-6-methyl-7,8-dihydropyrimido[4,5-d]pyrimidin-5-one Chemical compound NC1=NC(=C2C(=N1)NCN(C2=O)C)NC(C)C1=NC2=CC=CC(=C2C(N1C=1C=NC=CC=1)=O)Cl NSAGXRGAZQJOFN-UHFFFAOYSA-N 0.000 claims 1
- TZNDGRMDXQWHIR-UHFFFAOYSA-N 2-amino-4-[1-(5-fluoro-4-oxo-3-phenylquinazolin-2-yl)propylamino]-6-methyl-7,8-dihydropyrimido[4,5-d]pyrimidin-5-one Chemical compound NC1=NC(=C2C(=N1)NCN(C2=O)C)NC(CC)C1=NC2=CC=CC(=C2C(N1C1=CC=CC=C1)=O)F TZNDGRMDXQWHIR-UHFFFAOYSA-N 0.000 claims 1
- ZDWIJTRFCOGNND-UHFFFAOYSA-N 2-amino-4-[1-(6-fluoro-3-pyridin-2-ylquinolin-2-yl)ethylamino]-8H-pyrido[2,3-d]pyrimidin-5-one Chemical compound NC=1N=C(C2=C(N=1)NC=CC2=O)NC(C)C1=NC2=CC=C(C=C2C=C1C1=NC=CC=C1)F ZDWIJTRFCOGNND-UHFFFAOYSA-N 0.000 claims 1
- AMJZSPYKAAUSOO-UHFFFAOYSA-N 2-amino-4-[1-(8-chloro-1-oxo-2-phenylisoquinolin-3-yl)ethylamino]-6-methyl-7,8-dihydropyrimido[4,5-d]pyrimidin-5-one Chemical compound NC1=NC(=C2C(=N1)NCN(C2=O)C)NC(C)C=1N(C(C2=C(C=CC=C2C=1)Cl)=O)C1=CC=CC=C1 AMJZSPYKAAUSOO-UHFFFAOYSA-N 0.000 claims 1
- LUGWAPGDAFUVQD-UHFFFAOYSA-N 2-amino-4-[1-(8-chloro-1-oxo-2-phenylisoquinolin-3-yl)ethylamino]-6-methyl-8H-pyrido[2,3-d]pyrimidin-5-one Chemical compound NC=1N=C(C2=C(N=1)NC=C(C2=O)C)NC(C)C=1N(C(C2=C(C=CC=C2C=1)Cl)=O)C1=CC=CC=C1 LUGWAPGDAFUVQD-UHFFFAOYSA-N 0.000 claims 1
- RJVLJIIUMFKNLY-UHFFFAOYSA-N 2-amino-4-[1-(8-chloro-1-oxo-2-phenylisoquinolin-3-yl)ethylamino]-8H-pyrido[2,3-d]pyrimidin-5-one Chemical compound NC=1N=C(C2=C(N=1)NC=CC2=O)NC(C)C=1N(C(C2=C(C=CC=C2C=1)Cl)=O)C1=CC=CC=C1 RJVLJIIUMFKNLY-UHFFFAOYSA-N 0.000 claims 1
- HXDYYHAVZITKFU-UHFFFAOYSA-N 2-amino-4-[1-[5-chloro-3-(3-fluorophenyl)-4-oxoquinazolin-2-yl]ethylamino]-6-methyl-7,8-dihydropyrimido[4,5-d]pyrimidin-5-one Chemical compound NC1=NC(=C2C(=N1)NCN(C2=O)C)NC(C)C1=NC2=CC=CC(=C2C(N1C1=CC(=CC=C1)F)=O)Cl HXDYYHAVZITKFU-UHFFFAOYSA-N 0.000 claims 1
- CZXBWEJXAMZLNV-UHFFFAOYSA-N 2-amino-4-[1-[5-chloro-3-(3-methylphenyl)-4-oxoquinazolin-2-yl]ethylamino]-6-methyl-7,8-dihydropyrimido[4,5-d]pyrimidin-5-one Chemical compound NC1=NC(=C2C(=N1)NCN(C2=O)C)NC(C)C1=NC2=CC=CC(=C2C(N1C=1C=C(C=CC=1)C)=O)Cl CZXBWEJXAMZLNV-UHFFFAOYSA-N 0.000 claims 1
- KSJMJXDKCZACDO-UHFFFAOYSA-N 2-amino-4-[2-(5-chloro-4-oxo-3-phenylquinazolin-2-yl)pyrrolidin-1-yl]-6-methyl-7,8-dihydropyrimido[4,5-d]pyrimidin-5-one Chemical compound NC1=NC(=C2C(=N1)NCN(C2=O)C)N1C(CCC1)C1=NC2=CC=CC(=C2C(N1C1=CC=CC=C1)=O)Cl KSJMJXDKCZACDO-UHFFFAOYSA-N 0.000 claims 1
- SNLWXAYULQTORD-UHFFFAOYSA-N 2-amino-4-[2-(5-chloro-4-oxo-3-pyridin-3-ylquinazolin-2-yl)pyrrolidin-1-yl]-6-methyl-7,8-dihydropyrimido[4,5-d]pyrimidin-5-one Chemical compound NC1=NC(=C2C(=N1)NCN(C2=O)C)N1C(CCC1)C1=NC2=CC=CC(=C2C(N1C=1C=NC=CC=1)=O)Cl SNLWXAYULQTORD-UHFFFAOYSA-N 0.000 claims 1
- KYYMVIKCQZWFFY-UHFFFAOYSA-N 2-amino-4-[2-(8-chloro-1-oxo-2-phenylisoquinolin-3-yl)pyrrolidin-1-yl]-6-methyl-7,8-dihydropyrimido[4,5-d]pyrimidin-5-one Chemical compound NC1=NC(=C2C(=N1)NCN(C2=O)C)N1C(CCC1)C=1N(C(C2=C(C=CC=C2C=1)Cl)=O)C1=CC=CC=C1 KYYMVIKCQZWFFY-UHFFFAOYSA-N 0.000 claims 1
- JQJCZFDZJKNYIO-UHFFFAOYSA-N 2-amino-4-[2-(8-chloro-1-oxo-2-phenylisoquinolin-3-yl)pyrrolidin-1-yl]-8H-pyrido[2,3-d]pyrimidin-5-one Chemical compound NC=1N=C(C2=C(N=1)NC=CC2=O)N1C(CCC1)C=1N(C(C2=C(C=CC=C2C=1)Cl)=O)C1=CC=CC=C1 JQJCZFDZJKNYIO-UHFFFAOYSA-N 0.000 claims 1
- YLBBMYAJOBSIMG-UHFFFAOYSA-N 2-amino-4-[2-[5-chloro-3-(3-fluorophenyl)-4-oxoquinazolin-2-yl]pyrrolidin-1-yl]-6-methyl-7,8-dihydropyrimido[4,5-d]pyrimidin-5-one Chemical compound NC1=NC(=C2C(=N1)NCN(C2=O)C)N1C(CCC1)C1=NC2=CC=CC(=C2C(N1C1=CC(=CC=C1)F)=O)Cl YLBBMYAJOBSIMG-UHFFFAOYSA-N 0.000 claims 1
- BBWZBWYNLDJHFV-UHFFFAOYSA-N 2-amino-4-[2-[5-chloro-3-(3-methylphenyl)-4-oxoquinazolin-2-yl]pyrrolidin-1-yl]-6-methyl-7,8-dihydropyrimido[4,5-d]pyrimidin-5-one Chemical compound NC1=NC(=C2C(=N1)NCN(C2=O)C)N1C(CCC1)C1=NC2=CC=CC(=C2C(N1C=1C=C(C=CC=1)C)=O)Cl BBWZBWYNLDJHFV-UHFFFAOYSA-N 0.000 claims 1
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 1
- HIXUFHUKIOTXLJ-UHFFFAOYSA-N 4-[1-(4,8-dichloro-1-oxo-2-phenylisoquinolin-3-yl)ethylamino]-8H-pyrido[2,3-d]pyrimidin-5-one Chemical compound ClC1=C(N(C(C2=C(C=CC=C12)Cl)=O)C1=CC=CC=C1)C(C)NC=1C2=C(N=CN=1)NC=CC2=O HIXUFHUKIOTXLJ-UHFFFAOYSA-N 0.000 claims 1
- YTFASXLLVWHAGC-UHFFFAOYSA-N 4-[1-(5-chloro-4-oxo-3-phenylquinazolin-2-yl)ethylamino]-6-fluoro-8H-pyrido[2,3-d]pyrimidin-5-one Chemical compound ClC1=C2C(N(C(=NC2=CC=C1)C(C)NC=1C2=C(N=CN=1)NC=C(C2=O)F)C1=CC=CC=C1)=O YTFASXLLVWHAGC-UHFFFAOYSA-N 0.000 claims 1
- PUFWUBKHUMFHRB-UHFFFAOYSA-N 4-[1-(5-chloro-4-oxo-3-phenylquinazolin-2-yl)ethylamino]-6-methyl-7,8-dihydropyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C2C(N(C(=NC2=CC=C1)C(C)NC1=C2C(=NC=N1)NCN(C2=O)C)C1=CC=CC=C1)=O PUFWUBKHUMFHRB-UHFFFAOYSA-N 0.000 claims 1
- PBCJQVFRYHGDHV-UHFFFAOYSA-N 4-[1-(5-chloro-4-oxo-3-phenylquinazolin-2-yl)ethylamino]-8H-pyrido[2,3-d]pyrimidin-5-one Chemical compound ClC1=C2C(N(C(=NC2=CC=C1)C(C)NC=1C2=C(N=CN=1)NC=CC2=O)C1=CC=CC=C1)=O PBCJQVFRYHGDHV-UHFFFAOYSA-N 0.000 claims 1
- QBZSVOYHLGVQBB-UHFFFAOYSA-N 4-[1-(5-chloro-4-oxo-3-pyridin-2-ylquinazolin-2-yl)ethylamino]-8H-pyrido[2,3-d]pyrimidin-5-one Chemical compound ClC1=C2C(N(C(=NC2=CC=C1)C(C)NC=1C2=C(N=CN=1)NC=CC2=O)C1=NC=CC=C1)=O QBZSVOYHLGVQBB-UHFFFAOYSA-N 0.000 claims 1
- FSSMFLCLLOXKJZ-UHFFFAOYSA-N 4-[1-(5-chloro-4-oxo-3-pyridin-3-ylquinazolin-2-yl)ethylamino]-6-methyl-7,8-dihydropyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C2C(N(C(=NC2=CC=C1)C(C)NC1=C2C(=NC=N1)NCN(C2=O)C)C=1C=NC=CC=1)=O FSSMFLCLLOXKJZ-UHFFFAOYSA-N 0.000 claims 1
- KCNGEKNVSCQPEH-UHFFFAOYSA-N 4-[1-(5-chloro-4-oxo-3-pyridin-3-ylquinazolin-2-yl)ethylamino]-8H-pyrido[2,3-d]pyrimidin-5-one Chemical compound ClC1=C2C(N(C(=NC2=CC=C1)C(C)NC=1C2=C(N=CN=1)NC=CC2=O)C=1C=NC=CC=1)=O KCNGEKNVSCQPEH-UHFFFAOYSA-N 0.000 claims 1
- PFLBFVXDOSTCPK-UHFFFAOYSA-N 4-[1-(5-fluoro-4-oxo-3-phenylquinazolin-2-yl)propylamino]-6-methyl-7,8-dihydropyrimido[4,5-d]pyrimidin-5-one Chemical compound FC1=C2C(N(C(=NC2=CC=C1)C(CC)NC1=C2C(=NC=N1)NCN(C2=O)C)C1=CC=CC=C1)=O PFLBFVXDOSTCPK-UHFFFAOYSA-N 0.000 claims 1
- ZUMWCNRNNQTNEX-UHFFFAOYSA-N 4-[1-(5-fluoro-4-oxo-3-phenylquinazolin-2-yl)propylamino]-6-propan-2-yl-7,8-dihydropyrimido[4,5-d]pyrimidin-5-one Chemical compound FC1=C2C(N(C(=NC2=CC=C1)C(CC)NC1=C2C(=NC=N1)NCN(C2=O)C(C)C)C1=CC=CC=C1)=O ZUMWCNRNNQTNEX-UHFFFAOYSA-N 0.000 claims 1
- CTWPXRLVDBXWGK-UHFFFAOYSA-N 4-[1-(6-fluoro-3,4-dipyridin-2-ylquinolin-2-yl)ethylamino]-8H-pyrido[2,3-d]pyrimidin-5-one Chemical compound FC=1C=C2C(=C(C(=NC2=CC=1)C(C)NC=1C2=C(N=CN=1)NC=CC2=O)C1=NC=CC=C1)C1=NC=CC=C1 CTWPXRLVDBXWGK-UHFFFAOYSA-N 0.000 claims 1
- JZUATMHNJVCMGV-UHFFFAOYSA-N 4-[1-(6-fluoro-3-phenyl-4-pyridin-2-ylquinolin-2-yl)ethylamino]-8H-pyrido[2,3-d]pyrimidin-5-one Chemical compound FC=1C=C2C(=C(C(=NC2=CC=1)C(C)NC=1C2=C(N=CN=1)NC=CC2=O)C1=CC=CC=C1)C1=NC=CC=C1 JZUATMHNJVCMGV-UHFFFAOYSA-N 0.000 claims 1
- VVBDTGYSTYNFQX-UHFFFAOYSA-N 4-[1-(6-fluoro-4-oxo-3-phenylquinazolin-2-yl)ethylamino]-8H-pyrido[2,3-d]pyrimidin-5-one Chemical compound FC=1C=C2C(N(C(=NC2=CC=1)C(C)NC=1C2=C(N=CN=1)NC=CC2=O)C1=CC=CC=C1)=O VVBDTGYSTYNFQX-UHFFFAOYSA-N 0.000 claims 1
- NWHVAMSETRRPRH-UHFFFAOYSA-N 4-[1-(6-fluoro-4-oxo-3-pyridin-3-ylquinazolin-2-yl)ethylamino]-8H-pyrido[2,3-d]pyrimidin-5-one Chemical compound FC=1C=C2C(N(C(=NC2=CC=1)C(C)NC=1C2=C(N=CN=1)NC=CC2=O)C=1C=NC=CC=1)=O NWHVAMSETRRPRH-UHFFFAOYSA-N 0.000 claims 1
- KSVCDJHCMYATJY-UHFFFAOYSA-N 4-[1-(8-chloro-1-oxo-2-phenylisoquinolin-3-yl)ethylamino]-5-oxo-8H-pyrido[2,3-d]pyrimidine-6-carbonitrile Chemical compound ClC=1C=CC=C2C=C(N(C(C=12)=O)C1=CC=CC=C1)C(C)NC=1C2=C(N=CN=1)NC=C(C2=O)C#N KSVCDJHCMYATJY-UHFFFAOYSA-N 0.000 claims 1
- DPSBHJIGTWNPSV-UHFFFAOYSA-N 4-[1-(8-chloro-1-oxo-2-phenylisoquinolin-3-yl)ethylamino]-6-cyclopentyl-7,8-dihydropyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC=1C=CC=C2C=C(N(C(C=12)=O)C1=CC=CC=C1)C(C)NC1=C2C(=NC=N1)NCN(C2=O)C1CCCC1 DPSBHJIGTWNPSV-UHFFFAOYSA-N 0.000 claims 1
- SYYQRZUHOSHWLV-UHFFFAOYSA-N 4-[1-(8-chloro-1-oxo-2-phenylisoquinolin-3-yl)ethylamino]-6-cyclopropyl-7,8-dihydropyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC=1C=CC=C2C=C(N(C(C=12)=O)C1=CC=CC=C1)C(C)NC1=C2C(=NC=N1)NCN(C2=O)C1CC1 SYYQRZUHOSHWLV-UHFFFAOYSA-N 0.000 claims 1
- IGZTVXFMGQQVFY-UHFFFAOYSA-N 4-[1-(8-chloro-1-oxo-2-phenylisoquinolin-3-yl)ethylamino]-6-ethyl-7,8-dihydropyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC=1C=CC=C2C=C(N(C(C=12)=O)C1=CC=CC=C1)C(C)NC1=C2C(=NC=N1)NCN(C2=O)CC IGZTVXFMGQQVFY-UHFFFAOYSA-N 0.000 claims 1
- AUCUECQCKUQDGE-UHFFFAOYSA-N 4-[1-(8-chloro-1-oxo-2-phenylisoquinolin-3-yl)ethylamino]-6-fluoro-8H-pyrido[2,3-d]pyrimidin-5-one Chemical compound ClC=1C=CC=C2C=C(N(C(C=12)=O)C1=CC=CC=C1)C(C)NC=1C2=C(N=CN=1)NC=C(C2=O)F AUCUECQCKUQDGE-UHFFFAOYSA-N 0.000 claims 1
- OBDZPZJMXMBKID-UHFFFAOYSA-N 4-[1-(8-chloro-1-oxo-2-phenylisoquinolin-3-yl)ethylamino]-6-methyl-7,8-dihydropyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC=1C=CC=C2C=C(N(C(C=12)=O)C1=CC=CC=C1)C(C)NC1=C2C(=NC=N1)NCN(C2=O)C OBDZPZJMXMBKID-UHFFFAOYSA-N 0.000 claims 1
- NSYHBLNPOMJACP-UHFFFAOYSA-N 4-[1-(8-chloro-1-oxo-2-phenylisoquinolin-3-yl)ethylamino]-6-methyl-8H-pyrido[2,3-d]pyrimidin-5-one Chemical compound ClC=1C=CC=C2C=C(N(C(C=12)=O)C1=CC=CC=C1)C(C)NC=1C2=C(N=CN=1)NC=C(C2=O)C NSYHBLNPOMJACP-UHFFFAOYSA-N 0.000 claims 1
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2015-0086372 | 2015-06-18 | ||
| KR20150086372 | 2015-06-18 | ||
| KR1020160067210A KR101845931B1 (ko) | 2015-06-18 | 2016-05-31 | 헤테로아릴 유도체 또는 이의 약학적으로 허용가능한 염, 이의 제조방법 및 이를 유효성분으로 포함하는 pi3 키나아제 관련 질환의 예방 또는 치료용 약학적 조성물 |
| KR10-2016-0067210 | 2016-05-31 | ||
| PCT/KR2016/005798 WO2016204429A1 (ko) | 2015-06-18 | 2016-06-01 | 헤테로아릴 유도체 또는 이의 약학적으로 허용가능한 염, 이의 제조방법 및 이를 유효성분으로 포함하는 pi3 키나아제 관련 질환의 예방 또는 치료용 약학적 조성물. |
Publications (3)
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| JP2018522852A JP2018522852A (ja) | 2018-08-16 |
| JP2018522852A5 true JP2018522852A5 (OSRAM) | 2020-08-20 |
| JP6808905B2 JP6808905B2 (ja) | 2021-01-06 |
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| JP2017565779A Active JP6808905B2 (ja) | 2015-06-18 | 2016-06-01 | ヘテロアリール誘導体またはその薬学的に許容可能な塩、その製造方法、及びそれを有効成分として含むｐｉ３キナーゼ関連疾患の予防または治療用薬学的組成物 |
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| EP (1) | EP3312175B1 (OSRAM) |
| JP (1) | JP6808905B2 (OSRAM) |
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| CA (1) | CA2979815C (OSRAM) |
| ES (1) | ES2816050T3 (OSRAM) |
| HU (1) | HUE052332T2 (OSRAM) |
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| TW201938168A (zh) * | 2018-01-10 | 2019-10-01 | 韓商保寧製藥股份公司 | 預防或治療癌症之包含pi3激酶抑制劑與免疫檢查點抑制劑的醫藥組成物 |
| TW201934123A (zh) * | 2018-01-12 | 2019-09-01 | 韓商保寧製藥股份公司 | 預防或治療癌症之包含pi3激酶抑制劑與細胞毒性抗癌物的醫藥組成物 |
| WO2019143874A1 (en) | 2018-01-20 | 2019-07-25 | Sunshine Lake Pharma Co., Ltd. | Substituted aminopyrimidine compounds and methods of use |
| CN111018834B (zh) * | 2018-10-10 | 2022-07-15 | 成都理工大学 | 作为PPAR-γ调节剂的氨基嘧啶丁烯酮衍生物 |
| KR20200129705A (ko) * | 2019-05-09 | 2020-11-18 | 보령제약 주식회사 | 무정형의 pi3k 저해제 및 이를 포함하는 약학적 조성물 |
| KR20200129704A (ko) * | 2019-05-09 | 2020-11-18 | 보령제약 주식회사 | Pi3k 저해제의 결정다형 및 이의 제조방법 |
| KR102338609B1 (ko) * | 2019-05-20 | 2021-12-14 | 보령제약 주식회사 | 피리도-피리미딘 화합물 및 이를 유효성분으로 포함하는 pi3k 관련 질환의 예방 또는 치료용 약학적 조성물 |
| CN112194659A (zh) | 2019-07-08 | 2021-01-08 | 浙江海正药业股份有限公司 | 炔类衍生物及其制备方法和用途 |
| KR20210115375A (ko) * | 2020-03-12 | 2021-09-27 | 보령제약 주식회사 | Pi3 키나아제 저해제 및 btk 저해제를 포함하는 조성물 |
| WO2021201574A1 (ko) * | 2020-03-31 | 2021-10-07 | 보령제약 주식회사 | Pi3k 저해제로서의 화합물의 제조방법 및 이의 제조를 위한 중간체 화합물 |
| CN118373824A (zh) * | 2020-04-09 | 2024-07-23 | 成都赜灵生物医药科技有限公司 | 取代喹唑啉-4-酮类化合物及其制备方法和用途 |
| CN113527231A (zh) * | 2020-04-15 | 2021-10-22 | 深圳华大生命科学研究院 | 杂环取代腔肠素类化合物的合成方法 |
| US20230295158A1 (en) * | 2020-06-30 | 2023-09-21 | Boryung Corporation | Method for preparing compound as pi3k inhibitor and intermediate compound for preparing same |
| JP2024540257A (ja) * | 2021-11-03 | 2024-10-31 | ボリュン コーポレーション | Ｐｉ３ｋおよびｄｎａ－ｐｋ二重阻害剤を含む末梢性ｔ細胞リンパ腫の予防または治療用組成物 |
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| US1277738A (en) | 1916-04-03 | 1918-09-03 | American Can Co | Sardine-can. |
| CN1186324C (zh) | 2000-04-27 | 2005-01-26 | 山之内制药株式会社 | 稠合杂芳基衍生物 |
| PT2316831E (pt) | 2002-11-21 | 2013-06-06 | Novartis Ag | 2-(morfolin-4-il)pirimidinas como inibidores da fosfatidilinositol (pi) quinase e a sua utilização no tratamento do cancro |
| UA81790C2 (uk) * | 2002-12-19 | 2008-02-11 | Фармация Италия С.П.А. | Заміщені піролопіразольні похідні як інгібітори кінази |
| TW200938542A (en) * | 2008-02-01 | 2009-09-16 | Irm Llc | Compounds and compositions as kinase inhibitors |
| EA201270013A1 (ru) | 2009-06-25 | 2012-06-29 | Амген Инк. | Гетероциклические соединения и их применение |
| US8404677B2 (en) * | 2009-10-29 | 2013-03-26 | Genosco | Kinase inhibitors |
| WO2014015523A1 (en) * | 2012-07-27 | 2014-01-30 | Hutchison Medipharma Limited | Novel heteroaryl and heterocycle compounds, compositions and methods |
| GB201306610D0 (en) * | 2013-04-11 | 2013-05-29 | Almac Discovery Ltd | Pharmaceutical compounds |
| CN104151311B (zh) * | 2014-01-13 | 2017-01-04 | 华中师范大学 | 一类稠环化合物或其药学上可接受的盐及其制备方法和应用 |
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2016
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- 2016-06-01 PH PH1/2017/501989A patent/PH12017501989B1/en unknown
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- 2016-06-01 US US15/567,692 patent/US10526337B2/en active Active
- 2016-06-01 RU RU2017140446A patent/RU2719367C2/ru active
- 2016-06-01 AU AU2016279661A patent/AU2016279661B2/en active Active
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- 2016-06-01 MX MX2017014478A patent/MX385704B/es unknown
- 2016-06-01 CN CN201680030953.XA patent/CN107690433B/zh active Active
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