CA2953820A1 - Phosphatidylinositol 3-kinase inhibitors - Google Patents
Phosphatidylinositol 3-kinase inhibitors Download PDFInfo
- Publication number
- CA2953820A1 CA2953820A1 CA2953820A CA2953820A CA2953820A1 CA 2953820 A1 CA2953820 A1 CA 2953820A1 CA 2953820 A CA2953820 A CA 2953820A CA 2953820 A CA2953820 A CA 2953820A CA 2953820 A1 CA2953820 A1 CA 2953820A1
- Authority
- CA
- Canada
- Prior art keywords
- oxo
- amino
- dihydroquinazolin
- diamino
- carbonitrile
- 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.)
- Abandoned
Links
- 239000002935 phosphatidylinositol 3 kinase inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 427
- 239000000203 mixture Substances 0.000 claims abstract description 127
- 150000003839 salts Chemical class 0.000 claims abstract description 90
- 238000000034 method Methods 0.000 claims abstract description 77
- 108091007960 PI3Ks Proteins 0.000 claims abstract description 57
- 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 claims abstract description 53
- 238000011282 treatment Methods 0.000 claims abstract description 39
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
- 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 claims abstract description 7
- -1 C2-8heterocycloalkyl Chemical group 0.000 claims description 197
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 139
- 229910052739 hydrogen Inorganic materials 0.000 claims description 125
- 239000001257 hydrogen Substances 0.000 claims description 124
- 201000006417 multiple sclerosis Diseases 0.000 claims description 121
- 125000005843 halogen group Chemical group 0.000 claims description 117
- 125000001188 haloalkyl group Chemical group 0.000 claims description 93
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 79
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 78
- 125000000217 alkyl group Chemical group 0.000 claims description 74
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 64
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 63
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- 201000010099 disease Diseases 0.000 claims description 47
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- 229910006074 SO2NH2 Chemical group 0.000 claims description 8
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 8
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- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 7
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- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 3
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- 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 3
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- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
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- AHRQYOSAXZQCIG-UHFFFAOYSA-N pyrimidine-5-carbonitrile Chemical compound N#CC1=C=NC=N[CH]1 AHRQYOSAXZQCIG-UHFFFAOYSA-N 0.000 claims 17
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- 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 2
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- FBLRRWMYQHKTOW-IBGZPJMESA-N 2,4-diamino-6-[[(1S)-1-[4-oxo-3-phenyl-5-(3-piperidin-1-ylpropyl)quinazolin-2-yl]ethyl]amino]pyrimidine-5-carbonitrile Chemical compound NC1=NC(=C(C(=N1)N)C#N)N[C@@H](C)C1=NC2=CC=CC(=C2C(N1C1=CC=CC=C1)=O)CCCN1CCCCC1 FBLRRWMYQHKTOW-IBGZPJMESA-N 0.000 claims 1
- INIOPDJHPWFPSY-KRWDZBQOSA-N 2,4-diamino-6-[[(1S)-1-[5-(2-morpholin-4-ylethoxy)-4-oxo-3-phenylquinazolin-2-yl]ethyl]amino]pyrimidine-5-carbonitrile Chemical compound NC1=NC(=C(C(=N1)N)C#N)N[C@@H](C)C1=NC2=CC=CC(=C2C(N1C1=CC=CC=C1)=O)OCCN1CCOCC1 INIOPDJHPWFPSY-KRWDZBQOSA-N 0.000 claims 1
- DKCQVTGWFQVMMV-IBGZPJMESA-N 2,4-diamino-6-[[(1S)-1-[5-(3-cyclohexylpropyl)-4-oxo-3-phenylquinazolin-2-yl]ethyl]amino]pyrimidine-5-carbonitrile Chemical compound C[C@H](NC1=NC(N)=NC(N)=C1C#N)C1=NC2=CC=CC(CCCC3CCCCC3)=C2C(=O)N1C1=CC=CC=C1 DKCQVTGWFQVMMV-IBGZPJMESA-N 0.000 claims 1
- OFGZBSYIKRDFFE-SFHVURJKSA-N 2,4-diamino-6-[[(1S)-1-[5-(3-morpholin-4-ylpropyl)-4-oxo-3-phenylquinazolin-2-yl]ethyl]amino]pyrimidine-5-carbonitrile Chemical compound NC1=NC(=C(C(=N1)N)C#N)N[C@@H](C)C1=NC2=CC=CC(=C2C(N1C1=CC=CC=C1)=O)CCCN1CCOCC1 OFGZBSYIKRDFFE-SFHVURJKSA-N 0.000 claims 1
- SPLZMKYVCXYTBZ-ZENAZSQFSA-N 2,4-diamino-6-[[(1S)-1-[5-[2-(1-methylpyrrolidin-2-yl)ethoxy]-4-oxo-3-phenylquinazolin-2-yl]ethyl]amino]pyrimidine-5-carbonitrile Chemical compound NC1=NC(=C(C(=N1)N)C#N)N[C@@H](C)C1=NC2=CC=CC(=C2C(N1C1=CC=CC=C1)=O)OCCC1N(CCC1)C SPLZMKYVCXYTBZ-ZENAZSQFSA-N 0.000 claims 1
- OPAKIOVHYXWDSV-INIZCTEOSA-N 2,4-diamino-6-[[(1S)-1-[5-[2-(2-methylimidazol-1-yl)ethoxy]-4-oxo-3-phenylquinazolin-2-yl]ethyl]amino]pyrimidine-5-carbonitrile Chemical compound NC1=NC(=C(C(=N1)N)C#N)N[C@@H](C)C1=NC2=CC=CC(=C2C(N1C1=CC=CC=C1)=O)OCCN1C(=NC=C1)C OPAKIOVHYXWDSV-INIZCTEOSA-N 0.000 claims 1
- KCACXLBLOCLENE-SFHVURJKSA-N 2,4-diamino-6-[[(1S)-1-[5-[2-(4-methylpiperidin-1-yl)-2-oxoethoxy]-4-oxo-3-phenylquinazolin-2-yl]ethyl]amino]pyrimidine-5-carbonitrile Chemical compound NC1=NC(=C(C(=N1)N)C#N)N[C@@H](C)C1=NC2=CC=CC(=C2C(N1C1=CC=CC=C1)=O)OCC(=O)N1CCC(CC1)C KCACXLBLOCLENE-SFHVURJKSA-N 0.000 claims 1
- MRDUWJHFZONKJQ-IBGZPJMESA-N 2,4-diamino-6-[[(1S)-1-[5-[2-(azepan-1-yl)ethoxy]-4-oxo-3-phenylquinazolin-2-yl]ethyl]amino]pyrimidine-5-carbonitrile Chemical compound NC1=NC(=C(C(=N1)N)C#N)N[C@@H](C)C1=NC2=CC=CC(=C2C(N1C1=CC=CC=C1)=O)OCCN1CCCCCC1 MRDUWJHFZONKJQ-IBGZPJMESA-N 0.000 claims 1
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- UINSHMNWEIPLPN-FQEVSTJZSA-N 2,4-diamino-6-[[(1S)-1-[5-[3-(2-oxa-7-azaspiro[3.5]nonan-7-yl)propyl]-4-oxo-3-phenylquinazolin-2-yl]ethyl]amino]pyrimidine-5-carbonitrile Chemical compound C1OCC11CCN(CC1)CCCC1=C2C(N(C(=NC2=CC=C1)[C@H](C)NC1=NC(=NC(=C1C#N)N)N)C1=CC=CC=C1)=O UINSHMNWEIPLPN-FQEVSTJZSA-N 0.000 claims 1
- QKCSNQOGBIAHGM-INIZCTEOSA-N 2,4-diamino-6-[[(1S)-1-[5-[3-(3,3-difluoropyrrolidin-1-yl)propyl]-8-fluoro-4-oxo-3-phenylquinazolin-2-yl]ethyl]amino]pyrimidine-5-carbonitrile Chemical compound NC1=NC(=C(C(=N1)N)C#N)N[C@@H](C)C1=NC2=C(C=CC(=C2C(N1C1=CC=CC=C1)=O)CCCN1CC(CC1)(F)F)F QKCSNQOGBIAHGM-INIZCTEOSA-N 0.000 claims 1
- JJACAJXECQNVCV-IBGZPJMESA-N 2,4-diamino-6-[[(1S)-1-[5-[3-(3,3-dimethylmorpholin-4-yl)propyl]-4-oxo-3-phenylquinazolin-2-yl]ethyl]amino]pyrimidine-5-carbonitrile Chemical compound NC1=NC(=C(C(=N1)N)C#N)N[C@@H](C)C1=NC2=CC=CC(=C2C(N1C1=CC=CC=C1)=O)CCCN1C(COCC1)(C)C JJACAJXECQNVCV-IBGZPJMESA-N 0.000 claims 1
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- 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 1
- 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 1
- 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 1
- HTNPZVQEQLIDFG-IBGZPJMESA-N 2,4-diamino-6-[[(S)-cyclopropyl-[3-(3,5-difluorophenyl)-5-methyl-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)C)C1CC1 HTNPZVQEQLIDFG-IBGZPJMESA-N 0.000 claims 1
- OBKJDCQVRLWCPF-IBGZPJMESA-N 2,4-diamino-6-[[(S)-cyclopropyl-[3-(3-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=CC(=CC=C1)F)=O)S(=O)(=O)C)C1CC1 OBKJDCQVRLWCPF-IBGZPJMESA-N 0.000 claims 1
- VKAYRALOHIVHDI-SANMLTNESA-N 2,4-diamino-6-[[(S)-cyclopropyl-[4-oxo-3-phenyl-5-(3-piperidin-1-ylpropyl)quinazolin-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)=O)CCCN1CCCCC1)C1CC1 VKAYRALOHIVHDI-SANMLTNESA-N 0.000 claims 1
- UFDNKIYKUYKLPD-VWLOTQADSA-N 2,4-diamino-6-[[(S)-cyclopropyl-[4-oxo-3-phenyl-5-(3-pyrrolidin-1-ylpropyl)quinazolin-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)=O)CCCN1CCCC1)C1CC1 UFDNKIYKUYKLPD-VWLOTQADSA-N 0.000 claims 1
- WJJDKGUKVMJLCF-SFHVURJKSA-N 2,4-diamino-6-[[(S)-cyclopropyl-[5-fluoro-3-(3-fluorophenyl)-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)=O)F)C1CC1 WJJDKGUKVMJLCF-SFHVURJKSA-N 0.000 claims 1
- KRTLGTDEKUDJTP-SFHVURJKSA-N 2,4-diamino-6-[[(S)-cyclopropyl-[6-fluoro-3-(3-fluorophenyl)-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=C(C=C2C(N1C1=CC(=CC=C1)F)=O)F)C1CC1 KRTLGTDEKUDJTP-SFHVURJKSA-N 0.000 claims 1
- QMWZBPMJYIWZNG-VWLOTQADSA-N 2,4-diamino-6-[[(S)-cyclopropyl-[8-fluoro-4-oxo-3-phenyl-5-(3-piperidin-1-ylpropyl)quinazolin-2-yl]methyl]amino]pyrimidine-5-carbonitrile Chemical compound NC1=NC(=C(C(=N1)N)C#N)N[C@H](C1=NC2=C(C=CC(=C2C(N1C1=CC=CC=C1)=O)CCCN1CCCCC1)F)C1CC1 QMWZBPMJYIWZNG-VWLOTQADSA-N 0.000 claims 1
- SXBAVVZKRLYUCT-DEOSSOPVSA-N 2,4-diamino-6-[[(S)-cyclopropyl-[8-fluoro-4-oxo-3-phenyl-5-(3-pyrrolidin-1-ylpropyl)quinazolin-2-yl]methyl]amino]pyrimidine-5-carbonitrile Chemical compound NC1=NC(=C(C(=N1)N)C#N)N[C@H](C1=NC2=C(C=CC(=C2C(N1C1=CC=CC=C1)=O)CCCN1CCCC1)F)C1CC1 SXBAVVZKRLYUCT-DEOSSOPVSA-N 0.000 claims 1
- TXJHXFSNTZWCEU-LBPRGKRZSA-N 2-[(1S)-1-[(2-amino-5-iodo-6-methylpyrimidin-4-yl)amino]ethyl]-5-chloro-3-phenylquinazolin-4-one Chemical compound NC1=NC(=C(C(=N1)N[C@@H](C)C1=NC2=CC=CC(=C2C(N1C1=CC=CC=C1)=O)Cl)I)C TXJHXFSNTZWCEU-LBPRGKRZSA-N 0.000 claims 1
- LKNVBFDROWOHEN-VIFPVBQESA-N 2-[(1S)-1-[(6-amino-5-bromo-2-methylpyrimidin-4-yl)amino]ethyl]-5-chloro-3-(3,5-difluorophenyl)quinazolin-4-one Chemical compound C[C@H](NC1=C(Br)C(N)=NC(C)=N1)C1=NC2=CC=CC(Cl)=C2C(=O)N1C1=CC(F)=CC(F)=C1 LKNVBFDROWOHEN-VIFPVBQESA-N 0.000 claims 1
- GUALVYVRTVNIKR-NSHDSACASA-N 2-[(1S)-1-[(6-amino-5-bromo-2-methylpyrimidin-4-yl)amino]ethyl]-5-chloro-3-phenylquinazolin-4-one Chemical compound NC1=C(C(=NC(=N1)C)N[C@@H](C)C1=NC2=CC=CC(=C2C(N1C1=CC=CC=C1)=O)Cl)Br GUALVYVRTVNIKR-NSHDSACASA-N 0.000 claims 1
- VLLAMKWYMNGXCR-SFHVURJKSA-N 2-[(2S)-1-(2,6-diamino-5-cyanopyrimidin-4-yl)pyrrolidin-2-yl]-3-[3-(difluoromethyl)phenyl]-4-oxoquinazoline-8-carbonitrile Chemical compound NC1=NC(=C(C(=N1)N1[C@@H](CCC1)C1=NC2=C(C=CC=C2C(N1C1=CC(=CC=C1)C(F)F)=O)C#N)C#N)N VLLAMKWYMNGXCR-SFHVURJKSA-N 0.000 claims 1
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- ZQJYJSACBKJFQX-NSHDSACASA-N 2-amino-4-chloro-6-[[(1S)-1-(5-chloro-4-oxo-3-phenylquinazolin-2-yl)ethyl]amino]pyrimidine-5-carbonitrile Chemical compound NC1=NC(=C(C(=N1)Cl)C#N)N[C@@H](C)C1=NC2=CC=CC(=C2C(N1C1=CC=CC=C1)=O)Cl ZQJYJSACBKJFQX-NSHDSACASA-N 0.000 claims 1
- MFVIGWDJMOXJOT-JTQLQIEISA-N 2-amino-4-chloro-6-[[(1S)-1-(5-chloro-8-fluoro-4-oxo-3-phenylquinazolin-2-yl)ethyl]amino]pyrimidine-5-carbonitrile Chemical compound NC1=NC(=C(C(=N1)Cl)C#N)N[C@@H](C)C1=NC2=C(C=CC(=C2C(N1C1=CC=CC=C1)=O)Cl)F MFVIGWDJMOXJOT-JTQLQIEISA-N 0.000 claims 1
- DYELZWBIVBYNMV-VIFPVBQESA-N 2-amino-4-chloro-6-[[(1S)-1-[3-(3,5-difluorophenyl)-5-fluoro-4-oxoquinazolin-2-yl]ethyl]amino]pyrimidine-5-carbonitrile Chemical compound NC1=NC(=C(C(=N1)Cl)C#N)N[C@@H](C)C1=NC2=CC=CC(=C2C(N1C1=CC(=CC(=C1)F)F)=O)F DYELZWBIVBYNMV-VIFPVBQESA-N 0.000 claims 1
- OJXCRLCQACFFMY-VIFPVBQESA-N 2-amino-4-chloro-6-[[(1S)-1-[5-chloro-3-(3,5-difluorophenyl)-4-oxoquinazolin-2-yl]ethyl]amino]pyrimidine-5-carbonitrile Chemical compound NC1=NC(=C(C(=N1)Cl)C#N)N[C@@H](C)C1=NC2=CC=CC(=C2C(N1C1=CC(=CC(=C1)F)F)=O)Cl OJXCRLCQACFFMY-VIFPVBQESA-N 0.000 claims 1
- HSJFRYMHGBGZLC-ACJLOTCBSA-N 2-amino-N-[(3R,5S)-5-[5-chloro-3-(3,5-difluorophenyl)-4-oxoquinazolin-2-yl]-1-(2,6-diamino-5-cyanopyrimidin-4-yl)pyrrolidin-3-yl]acetamide Chemical compound NCC(=O)N[C@H]1CN([C@@H](C1)C1=NC2=CC=CC(=C2C(N1C1=CC(=CC(=C1)F)F)=O)Cl)C1=NC(=NC(=C1C#N)N)N HSJFRYMHGBGZLC-ACJLOTCBSA-N 0.000 claims 1
- SSPMSXIREWGDJA-JTQLQIEISA-N 3-[2-[(1S)-1-[(2,6-diamino-5-chloropyrimidin-4-yl)amino]ethyl]-3-(3,5-difluorophenyl)-4-oxoquinazolin-5-yl]propanamide Chemical compound NC1=NC(=C(C(=N1)N[C@@H](C)C1=NC2=CC=CC(=C2C(N1C1=CC(=CC(=C1)F)F)=O)CCC(=O)N)Cl)N SSPMSXIREWGDJA-JTQLQIEISA-N 0.000 claims 1
- YQDOMQGRYFOVLB-VIFPVBQESA-N 3-[2-[(1S)-1-[(2,6-diamino-5-chloropyrimidin-4-yl)amino]ethyl]-3-(3,5-difluorophenyl)-8-fluoro-4-oxoquinazolin-5-yl]propanamide Chemical compound NC1=NC(=C(C(=N1)N[C@@H](C)C1=NC2=C(C=CC(=C2C(N1C1=CC(=CC(=C1)F)F)=O)CCC(=O)N)F)Cl)N YQDOMQGRYFOVLB-VIFPVBQESA-N 0.000 claims 1
- PSSXHYGVMLDHIR-JTQLQIEISA-N 3-[2-[(1S)-1-[(2,6-diamino-5-cyanopyrimidin-4-yl)amino]ethyl]-3-(3,5-difluorophenyl)-8-fluoro-4-oxoquinazolin-5-yl]propanamide Chemical compound NC1=NC(=C(C(=N1)N[C@@H](C)C1=NC2=C(C=CC(=C2C(N1C1=CC(=CC(=C1)F)F)=O)CCC(=O)N)F)C#N)N PSSXHYGVMLDHIR-JTQLQIEISA-N 0.000 claims 1
- YWYXEDPNCIDLEF-ZDUSSCGKSA-N 3-[2-[(1S)-1-[(2,6-diamino-5-cyanopyrimidin-4-yl)amino]ethyl]-4-oxo-3-phenylquinazolin-5-yl]propanamide Chemical compound C[C@H](NC1=C(C#N)C(N)=NC(N)=N1)C1=NC2=CC=CC(CCC(N)=O)=C2C(=O)N1C1=CC=CC=C1 YWYXEDPNCIDLEF-ZDUSSCGKSA-N 0.000 claims 1
- XFQHUZWEHWWOGQ-LBPRGKRZSA-N 3-[2-[(1S)-1-[(2,6-diamino-5-cyanopyrimidin-4-yl)amino]ethyl]-8-fluoro-4-oxo-3-phenylquinazolin-5-yl]propanamide Chemical compound NC1=NC(=C(C(=N1)N[C@@H](C)C1=NC2=C(C=CC(=C2C(N1C1=CC=CC=C1)=O)CCC(=O)N)F)C#N)N XFQHUZWEHWWOGQ-LBPRGKRZSA-N 0.000 claims 1
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- JWLOUTWEPRZGNU-LBPRGKRZSA-N 4-[2-[(1S)-1-[(2,6-diamino-5-cyanopyrimidin-4-yl)amino]ethyl]-3-(3,5-difluorophenyl)-4-oxoquinazolin-5-yl]butanoic acid Chemical compound NC1=NC(=C(C(=N1)N[C@@H](C)C1=NC2=CC=CC(=C2C(N1C1=CC(=CC(=C1)F)F)=O)CCCC(=O)O)C#N)N JWLOUTWEPRZGNU-LBPRGKRZSA-N 0.000 claims 1
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Classifications
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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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Landscapes
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- Plural Heterocyclic Compounds (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462016194P | 2014-06-24 | 2014-06-24 | |
| US62/016,194 | 2014-06-24 | ||
| PCT/US2015/037234 WO2015200352A1 (en) | 2014-06-24 | 2015-06-23 | Phosphatidylinositol 3-kinase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2953820A1 true CA2953820A1 (en) | 2015-12-30 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2953820A Abandoned CA2953820A1 (en) | 2014-06-24 | 2015-06-23 | Phosphatidylinositol 3-kinase inhibitors |
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| US (2) | US9765060B2 (OSRAM) |
| EP (1) | EP3160960B1 (OSRAM) |
| JP (2) | JP6391718B2 (OSRAM) |
| KR (1) | KR20170015521A (OSRAM) |
| CN (1) | CN106459008A (OSRAM) |
| AR (1) | AR100975A1 (OSRAM) |
| AU (1) | AU2015280138B2 (OSRAM) |
| BR (1) | BR112016029846A2 (OSRAM) |
| CA (1) | CA2953820A1 (OSRAM) |
| EA (1) | EA201692487A1 (OSRAM) |
| ES (1) | ES2900812T3 (OSRAM) |
| HK (1) | HK1231474A1 (OSRAM) |
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| US20140213630A1 (en) | 2011-03-08 | 2014-07-31 | Thomas Diacovo | Methods and pharmaceutical compositions for treating lymphoid malignancy |
| EA201692266A1 (ru) | 2014-06-13 | 2017-06-30 | Джилид Сайэнс, Инк. | Ингибиторы фосфатидилинозитол-3-киназы |
| ES2763103T3 (es) | 2014-06-13 | 2020-05-27 | Gilead Sciences Inc | Inhibidor de la fosfatidilinositol 3-quinasa |
| NZ726360A (en) | 2014-06-13 | 2018-04-27 | Gilead Sciences Inc | Phosphatidylinositol 3-kinase inhibitors |
| CN106458932A (zh) | 2014-06-13 | 2017-02-22 | 吉利德科学公司 | 磷脂酰肌醇3‑激酶抑制剂 |
| MX2017000208A (es) | 2014-07-04 | 2017-05-01 | Lupin Ltd | Derivados de quinolizinona como inhibidores de pi3k. |
| TWI808055B (zh) | 2016-05-11 | 2023-07-11 | 美商滬亞生物國際有限公司 | Hdac 抑制劑與 pd-1 抑制劑之組合治療 |
| TWI794171B (zh) | 2016-05-11 | 2023-03-01 | 美商滬亞生物國際有限公司 | Ｈｄａｃ抑制劑與ｐｄ-ｌ１抑制劑之組合治療 |
| TW201815787A (zh) * | 2016-09-23 | 2018-05-01 | 美商基利科學股份有限公司 | 磷脂醯肌醇3-激酶抑制劑 |
| TW201813963A (zh) | 2016-09-23 | 2018-04-16 | 美商基利科學股份有限公司 | 磷脂醯肌醇3-激酶抑制劑 |
| TW201825465A (zh) | 2016-09-23 | 2018-07-16 | 美商基利科學股份有限公司 | 磷脂醯肌醇3-激酶抑制劑 |
| CN106632077B (zh) * | 2016-10-10 | 2019-01-22 | 上海再启生物技术有限公司 | 一种2-氨基-4-溴嘧啶的制备方法 |
| US10396145B2 (en) * | 2017-01-12 | 2019-08-27 | Micron Technology, Inc. | Memory cells comprising ferroelectric material and including current leakage paths having different total resistances |
| WO2018237007A1 (en) * | 2017-06-22 | 2018-12-27 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Inhibitors of phosphoinositide 3-kinase and histone deacetylase for treatment of cancer |
| SG11202000523PA (en) * | 2017-07-31 | 2020-02-27 | The Trustees Of Columbia Univeristy In The City Of New York | Compounds, compositions, and methods for treating t-cell acute lymphoblastic leukemia |
| US10751339B2 (en) | 2018-01-20 | 2020-08-25 | Sunshine Lake Pharma Co., Ltd. | Substituted aminopyrimidine compounds and methods of use |
| EA202190880A1 (ru) * | 2018-09-27 | 2021-06-28 | Шанхай Инли Фармасьютикал Ко., Лтд | Кристаллическая форма морфолинохиназолинового соединения, способ ее получения и ее применение |
| US20220348558A1 (en) * | 2019-09-05 | 2022-11-03 | Wisconsin Alumni Research Foundation | Inhibitors of encephalitic alphaviruses |
| CN110590681B (zh) * | 2019-09-30 | 2021-06-01 | 中山大学 | 一种新型喹唑啉酮类化合物及其制备方法和应用 |
| CN114929709B (zh) * | 2019-10-29 | 2024-08-30 | 比奥根Ma公司 | 螺环o-糖蛋白-2-乙酰胺基-2-脱氧-3-d-吡喃葡萄糖苷酶抑制剂 |
| 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 |
| WO2024064024A1 (en) * | 2022-09-19 | 2024-03-28 | Onkure, Inc. | ((4-oxo-3,4-dihydroquinazolin-8-yl)methyl)amine derivatives as p13k inhibitors for the treatment of cancer |
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| US6667300B2 (en) * | 2000-04-25 | 2003-12-23 | Icos Corporation | Inhibitors of human phosphatidylinositol 3-kinase delta |
| KR100785363B1 (ko) | 2000-04-25 | 2007-12-18 | 이코스 코포레이션 | 인간 포스파티딜-이노시톨 3-키나제 델타의 억제제 |
| US8193182B2 (en) * | 2008-01-04 | 2012-06-05 | Intellikine, Inc. | Substituted isoquinolin-1(2H)-ones, and methods of use thereof |
| WO2009088990A1 (en) * | 2008-01-04 | 2009-07-16 | Intellikine, Inc. | Certain chemical entities, compositions and methods |
| US8604032B2 (en) * | 2010-05-21 | 2013-12-10 | Infinity Pharmaceuticals, Inc. | Chemical compounds, compositions and methods for kinase modulation |
| RU2014111823A (ru) * | 2011-08-29 | 2015-10-10 | Инфинити Фармасьютикалз, Инк. | Гетероциклические соединения и их применения |
| CA2895785A1 (en) * | 2012-12-21 | 2014-06-26 | Jerry Evarts | Isoquinolinone or quinazolinone phosphatidylinositol 3-kinase inhibitors |
| WO2014128612A1 (en) | 2013-02-20 | 2014-08-28 | Novartis Ag | Quinazolin-4-one derivatives |
| UY35675A (es) * | 2013-07-24 | 2015-02-27 | Novartis Ag | Derivados sustituidos de quinazolin-4-ona |
| AU2014354769A1 (en) * | 2013-11-26 | 2016-05-26 | Gilead Sciences, Inc. | Therapies for treating myeloproliferative disorders |
| WO2015168079A1 (en) | 2014-04-29 | 2015-11-05 | Infinity Pharmaceuticals, Inc. | Pyrimidine or pyridine derivatives useful as pi3k inhibitors |
| ES2763103T3 (es) * | 2014-06-13 | 2020-05-27 | Gilead Sciences Inc | Inhibidor de la fosfatidilinositol 3-quinasa |
| NZ726360A (en) * | 2014-06-13 | 2018-04-27 | Gilead Sciences Inc | Phosphatidylinositol 3-kinase inhibitors |
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2015
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- 2015-06-23 CN CN201580034671.2A patent/CN106459008A/zh active Pending
- 2015-06-23 SG SG11201610341PA patent/SG11201610341PA/en unknown
- 2015-06-23 EA EA201692487A patent/EA201692487A1/ru unknown
- 2015-06-23 US US14/747,931 patent/US9765060B2/en active Active
- 2015-06-23 NZ NZ727185A patent/NZ727185A/en not_active IP Right Cessation
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- 2015-06-23 WO PCT/US2015/037234 patent/WO2015200352A1/en not_active Ceased
- 2015-06-23 ES ES15739079T patent/ES2900812T3/es active Active
- 2015-06-23 CA CA2953820A patent/CA2953820A1/en not_active Abandoned
- 2015-06-23 AU AU2015280138A patent/AU2015280138B2/en not_active Ceased
- 2015-06-23 HK HK17105165.9A patent/HK1231474A1/zh unknown
- 2015-06-23 KR KR1020177001682A patent/KR20170015521A/ko not_active Abandoned
- 2015-06-23 JP JP2016574424A patent/JP6391718B2/ja not_active Expired - Fee Related
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- 2015-06-24 TW TW104120373A patent/TW201625558A/zh unknown
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2016
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2017
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2018
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| US20160024054A1 (en) | 2016-01-28 |
| NZ727185A (en) | 2018-04-27 |
| AU2015280138B2 (en) | 2018-06-14 |
| HK1231474A1 (zh) | 2017-12-22 |
| SG11201610341PA (en) | 2017-01-27 |
| IL249404A0 (en) | 2017-02-28 |
| EP3160960B1 (en) | 2021-10-13 |
| AR100975A1 (es) | 2016-11-16 |
| JP6391718B2 (ja) | 2018-09-19 |
| MA40045A (fr) | 2021-06-02 |
| JP2017519021A (ja) | 2017-07-13 |
| CN106459008A (zh) | 2017-02-22 |
| EA201692487A1 (ru) | 2017-06-30 |
| US20180065953A1 (en) | 2018-03-08 |
| KR20170015521A (ko) | 2017-02-08 |
| MX2016017110A (es) | 2017-05-01 |
| WO2015200352A1 (en) | 2015-12-30 |
| TW201625558A (zh) | 2016-07-16 |
| ES2900812T3 (es) | 2022-03-18 |
| JP2018090644A (ja) | 2018-06-14 |
| EP3160960A1 (en) | 2017-05-03 |
| BR112016029846A2 (pt) | 2017-08-22 |
| AU2015280138A1 (en) | 2016-12-22 |
| US9765060B2 (en) | 2017-09-19 |
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