JP6391718B2 - ホスファチジルイノシトール３−キナーゼ阻害剤 - Google Patents

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Publication number

JP6391718B2

JP6391718B2 JP2016574424A JP2016574424A JP6391718B2 JP 6391718 B2 JP6391718 B2 JP 6391718B2 JP 2016574424 A JP2016574424 A JP 2016574424A JP 2016574424 A JP2016574424 A JP 2016574424A JP 6391718 B2 JP6391718 B2 JP 6391718B2

Authority

JP

Japan

Prior art keywords

alkylene

oxo

alkyl

diamino

dihydroquinazolin

Prior art date

2014-06-24

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.)

Expired - Fee Related

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• 229940043441 phosphoinositide 3-kinase inhibitor Drugs 0.000 title description 8
• 239000002935 phosphatidylinositol 3 kinase inhibitor Substances 0.000 title 1
• -1 OR 1x Chemical group 0.000 claims description 432
• 150000001875 compounds Chemical class 0.000 claims description 416
• 125000000217 alkyl group Chemical group 0.000 claims description 281
• 229910052739 hydrogen Inorganic materials 0.000 claims description 132
• 125000005843 halogen group Chemical group 0.000 claims description 131
• 239000000203 mixture Substances 0.000 claims description 129
• 239000001257 hydrogen Substances 0.000 claims description 128
• 150000003839 salts Chemical class 0.000 claims description 122
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 120
• 125000001188 haloalkyl group Chemical group 0.000 claims description 108
• 125000003118 aryl group Chemical group 0.000 claims description 107
• 201000006417 multiple sclerosis Diseases 0.000 claims description 107
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 92
• 125000001072 heteroaryl group Chemical group 0.000 claims description 77
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 72
• 238000000034 method Methods 0.000 claims description 71
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 65
• 125000002947 alkylene group Chemical group 0.000 claims description 60
• 125000001153 fluoro group Chemical group F* 0.000 claims description 58
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 55
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 51
• 230000000694 effects Effects 0.000 claims description 51
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 51
• 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 claims description 50
• 201000010099 disease Diseases 0.000 claims description 48
• 125000002757 morpholinyl group Chemical group 0.000 claims description 47
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 47
• 125000002393 azetidinyl group Chemical group 0.000 claims description 45
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 45
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 45
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 44
• XVIAPHVAGFEFFN-UHFFFAOYSA-N pyrimidine-5-carbonitrile Chemical compound N#CC1=CN=CN=C1 XVIAPHVAGFEFFN-UHFFFAOYSA-N 0.000 claims description 37
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 35
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
• 125000000623 heterocyclic group Chemical group 0.000 claims description 32
• 125000003386 piperidinyl group Chemical group 0.000 claims description 32
• 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 32
• 125000004429 atom Chemical group 0.000 claims description 31
• 125000003725 azepanyl group Chemical group 0.000 claims description 31
• 125000003566 oxetanyl group Chemical group 0.000 claims description 30
• 125000004193 piperazinyl group Chemical group 0.000 claims description 29
• 125000001424 substituent group Chemical group 0.000 claims description 29
• 125000005842 heteroatom Chemical group 0.000 claims description 28
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
• 125000002883 imidazolyl group Chemical group 0.000 claims description 27
• 125000004043 oxo group Chemical group O=* 0.000 claims description 26
• 239000003814 drug Substances 0.000 claims description 24
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 20
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 19
• 206010028980 Neoplasm Diseases 0.000 claims description 19
• 230000002401 inhibitory effect Effects 0.000 claims description 19
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 18
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 16
• 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 16
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
• 125000001963 4 membered heterocyclic group Chemical group 0.000 claims description 15
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 15
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 15
• 206010025323 Lymphomas Diseases 0.000 claims description 14
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 14
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 14
• 125000003545 alkoxy group Chemical group 0.000 claims description 13
• 125000006001 difluoroethyl group Chemical group 0.000 claims description 13
• 230000005764 inhibitory process Effects 0.000 claims description 13
• 239000008194 pharmaceutical composition Substances 0.000 claims description 13
• 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 12
• 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims description 11
• 201000011510 cancer Diseases 0.000 claims description 11
• 229910052757 nitrogen Inorganic materials 0.000 claims description 11
• 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 10
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
• 229910052760 oxygen Inorganic materials 0.000 claims description 9
• 239000001301 oxygen Chemical group 0.000 claims description 9
• 229910052717 sulfur Chemical group 0.000 claims description 9
• 239000011593 sulfur Chemical group 0.000 claims description 9
• NRNZOLOAHSMLGT-IBGZPJMESA-N 2,4-diamino-6-[[(S)-cyclopropyl-[3-(2-fluorophenyl)-5-methylsulfonyl-4-oxoquinazolin-2-yl]methyl]amino]pyrimidine-5-carbonitrile Chemical compound NC1=NC(=C(C(=N1)N)C#N)N[C@H](C1=NC2=CC=CC(=C2C(N1C1=C(C=CC=C1)F)=O)S(=O)(=O)C)C1CC1 NRNZOLOAHSMLGT-IBGZPJMESA-N 0.000 claims description 8
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 8
• 208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 claims description 8
• 208000025205 Mantle-Cell Lymphoma Diseases 0.000 claims description 8
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 8
• 208000029052 T-cell acute lymphoblastic leukemia Diseases 0.000 claims description 8
• 206010012818 diffuse large B-cell lymphoma Diseases 0.000 claims description 8
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 8
• 229920006395 saturated elastomer Polymers 0.000 claims description 8
• 208000025324 B-cell acute lymphoblastic leukemia Diseases 0.000 claims description 7
• 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims description 7
• 201000003793 Myelodysplastic syndrome Diseases 0.000 claims description 7
• 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 claims description 7
• 206010035226 Plasma cell myeloma Diseases 0.000 claims description 7
• 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims description 7
• 208000033559 Waldenström macroglobulinemia Diseases 0.000 claims description 7
• 229920001184 polypeptide Polymers 0.000 claims description 7
• 108090000765 processed proteins & peptides Proteins 0.000 claims description 7
• 102000004196 processed proteins & peptides Human genes 0.000 claims description 7
• 238000002560 therapeutic procedure Methods 0.000 claims description 7
• ODNMMTBDMCMWIA-KRWDZBQOSA-N 2,4-diamino-6-[(2S)-2-[3-(2-fluorophenyl)-5-methylsulfonyl-4-oxoquinazolin-2-yl]pyrrolidin-1-yl]pyrimidine-5-carbonitrile Chemical compound NC1=NC(=C(C(=N1)N)C#N)N1[C@@H](CCC1)C1=NC2=CC=CC(=C2C(N1C1=C(C=CC=C1)F)=O)S(=O)(=O)C ODNMMTBDMCMWIA-KRWDZBQOSA-N 0.000 claims description 6
• LTJDTZLNOJTXMS-KRWDZBQOSA-N 2,4-diamino-6-[(2S)-2-[3-(3-fluorophenyl)-5-methylsulfonyl-4-oxoquinazolin-2-yl]pyrrolidin-1-yl]pyrimidine-5-carbonitrile Chemical compound NC1=NC(=C(C(=N1)N)C#N)N1[C@@H](CCC1)C1=NC2=CC=CC(=C2C(N1C1=CC(=CC=C1)F)=O)S(=O)(=O)C LTJDTZLNOJTXMS-KRWDZBQOSA-N 0.000 claims description 6
• 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims description 6
• 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims description 6
• 208000037538 Myelomonocytic Juvenile Leukemia Diseases 0.000 claims description 6
• 208000014767 Myeloproliferative disease Diseases 0.000 claims description 6
• XCUAIINAJCDIPM-XVFCMESISA-N N(4)-hydroxycytidine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=NO)C=C1 XCUAIINAJCDIPM-XVFCMESISA-N 0.000 claims description 6
• 201000004681 Psoriasis Diseases 0.000 claims description 6
• 208000007660 Residual Neoplasm Diseases 0.000 claims description 6
• 201000005992 juvenile myelomonocytic leukemia Diseases 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
• 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 6
• VBFRFRVPVIHNJU-HNNXBMFYSA-N 5-chloro-2-[(3R)-4-(2,6-diamino-5-chloropyrimidin-4-yl)morpholin-3-yl]-3-phenylquinazolin-4-one Chemical compound [H][C@]1(COCCN1C1=NC(N)=NC(N)=C1Cl)C1=NC2=CC=CC(Cl)=C2C(=O)N1C1=CC=CC=C1 VBFRFRVPVIHNJU-HNNXBMFYSA-N 0.000 claims description 5
• 208000016025 Waldenstroem macroglobulinemia Diseases 0.000 claims description 5
• 208000006673 asthma Diseases 0.000 claims description 5
• XHDIMAWEQARQER-INIZCTEOSA-N 2,4-diamino-6-[(2S)-2-[3-(2,6-difluorophenyl)-5-methylsulfonyl-4-oxoquinazolin-2-yl]pyrrolidin-1-yl]pyrimidine-5-carbonitrile Chemical compound NC1=NC(=C(C(=N1)N)C#N)N1[C@@H](CCC1)C1=NC2=CC=CC(=C2C(N1C1=C(C=CC=C1F)F)=O)S(=O)(=O)C XHDIMAWEQARQER-INIZCTEOSA-N 0.000 claims description 4
• 208000003950 B-cell lymphoma Diseases 0.000 claims description 4
• 206010006187 Breast cancer Diseases 0.000 claims description 4
• 208000026310 Breast neoplasm Diseases 0.000 claims description 4
• 208000011691 Burkitt lymphomas Diseases 0.000 claims description 4
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
• 206010009944 Colon cancer Diseases 0.000 claims description 4
• 208000008839 Kidney Neoplasms Diseases 0.000 claims description 4
• 208000034578 Multiple myelomas Diseases 0.000 claims description 4
• 206010033128 Ovarian cancer Diseases 0.000 claims description 4
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 4
• 206010060862 Prostate cancer Diseases 0.000 claims description 4
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• 206010038389 Renal cancer Diseases 0.000 claims description 4
• 201000007455 central nervous system cancer Diseases 0.000 claims description 4
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• 201000007924 marginal zone B-cell lymphoma Diseases 0.000 claims description 4
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• 230000009885 systemic effect Effects 0.000 claims description 4
• XZFQZIDTKMMORZ-KRWDZBQOSA-N 2,4-diamino-6-[(2S)-2-[3-(3,5-difluorophenyl)-5-fluoro-4-oxoquinazolin-2-yl]pyrrolidin-1-yl]pyrimidine-5-carbonitrile Chemical compound NC1=NC(=C(C(=N1)N)C#N)N1[C@@H](CCC1)C1=NC2=CC=CC(=C2C(N1C1=CC(=CC(=C1)F)F)=O)F XZFQZIDTKMMORZ-KRWDZBQOSA-N 0.000 claims description 3
• ULIPIDUOYUPPGA-SFHVURJKSA-N 2,4-diamino-6-[(2S)-2-[3-(3,5-difluorophenyl)-8-methyl-4-oxoquinazolin-2-yl]pyrrolidin-1-yl]pyrimidine-5-carbonitrile Chemical compound NC1=NC(=C(C(=N1)N)C#N)N1[C@@H](CCC1)C1=NC2=C(C=CC=C2C(N1C1=CC(=CC(=C1)F)F)=O)C ULIPIDUOYUPPGA-SFHVURJKSA-N 0.000 claims description 3
• UBCROLIANMOUOT-IBYPIGCZSA-N 2,4-diamino-6-[(2S)-2-[5-chloro-3-(3,5-difluorophenyl)-4-oxoquinazolin-2-yl]-4-methoxypyrrolidin-1-yl]pyrimidine-5-carbonitrile Chemical compound NC1=NC(=C(C(=N1)N)C#N)N1[C@@H](CC(C1)OC)C1=NC2=CC=CC(=C2C(N1C1=CC(=CC(=C1)F)F)=O)Cl UBCROLIANMOUOT-IBYPIGCZSA-N 0.000 claims description 3
• FCOTXTGOPHPHDV-INIZCTEOSA-N 2,4-diamino-6-[(2S)-2-[5-chloro-3-(3,5-difluorophenyl)-4-oxoquinazolin-2-yl]azetidin-1-yl]pyrimidine-5-carbonitrile Chemical compound [H][C@]1(CCN1C1=C(C#N)C(N)=NC(N)=N1)C1=NC2=CC=CC(Cl)=C2C(=O)N1C1=CC(F)=CC(F)=C1 FCOTXTGOPHPHDV-INIZCTEOSA-N 0.000 claims description 3
• HNVQQPZDIGHQII-KRWDZBQOSA-N 2,4-diamino-6-[(2S)-2-[5-chloro-3-(3,5-difluorophenyl)-4-oxoquinazolin-2-yl]pyrrolidin-1-yl]pyrimidine-5-carbonitrile Chemical compound NC1=NC(=C(C(=N1)N)C#N)N1[C@@H](CCC1)C1=NC2=CC=CC(=C2C(N1C1=CC(=CC(=C1)F)F)=O)Cl HNVQQPZDIGHQII-KRWDZBQOSA-N 0.000 claims description 3
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• FFZIQDWOFOXVDY-SFHVURJKSA-N 2,4-diamino-6-[(2S)-2-[5-chloro-3-(3-cyano-5-fluorophenyl)-4-oxoquinazolin-2-yl]pyrrolidin-1-yl]pyrimidine-5-carbonitrile Chemical compound NC1=NC(=C(C(=N1)N)C#N)N1[C@@H](CCC1)C1=NC2=CC=CC(=C2C(N1C1=CC(=CC(=C1)F)C#N)=O)Cl FFZIQDWOFOXVDY-SFHVURJKSA-N 0.000 claims description 3
• DCUIDXPXCJSQIC-ACJLOTCBSA-N 2,4-diamino-6-[(2S,4R)-2-(5-chloro-4-oxo-3-phenylquinazolin-2-yl)-4-methylpyrrolidin-1-yl]pyrimidine-5-carbonitrile Chemical compound NC1=NC(=C(C(=N1)N)C#N)N1[C@@H](C[C@H](C1)C)C1=NC2=CC=CC(=C2C(N1C1=CC=CC=C1)=O)Cl DCUIDXPXCJSQIC-ACJLOTCBSA-N 0.000 claims description 3
• UVECEKSYBYUSKF-PXAZEXFGSA-N 2,4-diamino-6-[(2S,4R)-2-[5-chloro-3-(3,5-difluorophenyl)-4-oxoquinazolin-2-yl]-4-fluoropyrrolidin-1-yl]pyrimidine-5-carbonitrile Chemical compound NC1=NC(=C(C(=N1)N)C#N)N1[C@@H](C[C@H](C1)F)C1=NC2=CC=CC(=C2C(N1C1=CC(=CC(=C1)F)F)=O)Cl UVECEKSYBYUSKF-PXAZEXFGSA-N 0.000 claims description 3
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• NRJSHKSODUMLII-FQEVSTJZSA-N 2,4-diamino-6-[[(S)-[3-(3-cyano-5-fluorophenyl)-5-methyl-4-oxoquinazolin-2-yl]-cyclopropylmethyl]amino]pyrimidine-5-carbonitrile Chemical compound NC1=NC(=C(C(=N1)N)C#N)N[C@@H](C1CC1)C1=NC2=CC=CC(=C2C(N1C1=CC(=CC(=C1)F)C#N)=O)C NRJSHKSODUMLII-FQEVSTJZSA-N 0.000 claims description 3
• HARCUZQNOFNGEA-SFHVURJKSA-N 2,4-diamino-6-[[(S)-[5-chloro-3-(3,5-difluorophenyl)-4-oxoquinazolin-2-yl]-cyclopropylmethyl]amino]pyrimidine-5-carbonitrile Chemical compound NC1=NC(=C(C(=N1)N)C#N)N[C@@H](C1CC1)C1=NC2=CC=CC(=C2C(N1C1=CC(=CC(=C1)F)F)=O)Cl HARCUZQNOFNGEA-SFHVURJKSA-N 0.000 claims description 3
• DRDYADBTFZGAJP-SFHVURJKSA-N 2,4-diamino-6-[[(S)-cyclopropyl-[3-(2,6-difluorophenyl)-5-methylsulfonyl-4-oxoquinazolin-2-yl]methyl]amino]pyrimidine-5-carbonitrile Chemical compound NC1=NC(=C(C(=N1)N)C#N)N[C@H](C1=NC2=CC=CC(=C2C(N1C1=C(C=CC=C1F)F)=O)S(=O)(=O)C)C1CC1 DRDYADBTFZGAJP-SFHVURJKSA-N 0.000 claims description 3
• SJZQRPNTRXQNBH-SFHVURJKSA-N 2,4-diamino-6-[[(S)-cyclopropyl-[3-(3,5-difluorophenyl)-5-fluoro-4-oxoquinazolin-2-yl]methyl]amino]pyrimidine-5-carbonitrile Chemical compound NC1=NC(=C(C(=N1)N)C#N)N[C@H](C1=NC2=CC=CC(=C2C(N1C1=CC(=CC(=C1)F)F)=O)F)C1CC1 SJZQRPNTRXQNBH-SFHVURJKSA-N 0.000 claims description 3
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• TWHKASHPBXEZBH-IBGZPJMESA-N 2-[(S)-cyclopropyl-[(2,6-diamino-5-cyanopyrimidin-4-yl)amino]methyl]-3-[3-(difluoromethyl)-5-fluorophenyl]-4-oxoquinazoline-5-carbonitrile Chemical compound C1(CC1)[C@@H](C1=NC=2C=CC=C(C=2C(N1C1=CC(=CC(=C1)F)C(F)F)=O)C#N)NC1=NC(=NC(=C1C#N)N)N TWHKASHPBXEZBH-IBGZPJMESA-N 0.000 claims description 3
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• WDKDKOGDFAMTQW-FQEVSTJZSA-N 4-[2-[(2S)-1-(2,6-diamino-5-cyanopyrimidin-4-yl)pyrrolidin-2-yl]-4-oxo-3-phenylquinazolin-5-yl]butanoic acid Chemical compound NC1=NC(=C(C(=N1)N1[C@@H](CCC1)C1=NC2=CC=CC(=C2C(N1C1=CC=CC=C1)=O)CCCC(=O)O)C#N)N WDKDKOGDFAMTQW-FQEVSTJZSA-N 0.000 claims description 3
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