RU2509081C2 - Пуриновые соединения, ингибирующие рi3к, и способы применения - Google Patents

Info

Publication number

RU2509081C2

RU2509081C2 RU2010154428/04A RU2010154428A RU2509081C2 RU 2509081 C2 RU2509081 C2 RU 2509081C2 RU 2010154428/04 A RU2010154428/04 A RU 2010154428/04A RU 2010154428 A RU2010154428 A RU 2010154428A RU 2509081 C2 RU2509081 C2 RU 2509081C2

Authority

RU

Russia

Prior art keywords

purin

morpholino

methyl

aminopyrimidin

heterocyclyl

Prior art date

2008-05-30

Links

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• Global Dossier
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• 238000000034 method Methods 0.000 title claims description 159
• 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 title abstract 2
• 230000002401 inhibitory effect Effects 0.000 title description 7
• 150000001875 compounds Chemical class 0.000 claims abstract description 195
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 50
• 150000003839 salts Chemical class 0.000 claims abstract description 34
• 125000003118 aryl group Chemical group 0.000 claims abstract description 33
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 30
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 28
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 26
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 20
• 229910052801 chlorine Inorganic materials 0.000 claims abstract description 14
• 229910052731 fluorine Inorganic materials 0.000 claims abstract description 11
• 229910052740 iodine Inorganic materials 0.000 claims abstract description 11
• 229910052794 bromium Inorganic materials 0.000 claims abstract description 10
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 10
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 6
• 239000001301 oxygen Substances 0.000 claims abstract description 6
• -1 4- (methylsulfonyl) piperazin-1-yl Chemical group 0.000 claims description 182
• 125000002947 alkylene group Chemical group 0.000 claims description 34
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 29
• 239000008194 pharmaceutical composition Substances 0.000 claims description 24
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
• 229910052799 carbon Inorganic materials 0.000 claims description 19
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 17
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 12
• 239000003085 diluting agent Substances 0.000 claims description 11
• 238000004519 manufacturing process Methods 0.000 claims description 9
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
• 238000002156 mixing Methods 0.000 claims description 8
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 7
• KQNBNJOVKJOMDH-UHFFFAOYSA-N 2-[2-(2-aminopyrimidin-5-yl)-6-morpholin-4-yl-9-propylpurin-8-yl]propan-2-ol Chemical compound N1=C2N(CCC)C(C(C)(C)O)=NC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 KQNBNJOVKJOMDH-UHFFFAOYSA-N 0.000 claims description 6
• QJGFOGJKIDPKSZ-UHFFFAOYSA-N 2-[2-(2-aminopyrimidin-5-yl)-9-butyl-6-morpholin-4-ylpurin-8-yl]propan-2-ol Chemical compound N1=C2N(CCCC)C(C(C)(C)O)=NC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 QJGFOGJKIDPKSZ-UHFFFAOYSA-N 0.000 claims description 6
• YWTFMRUDEJHZGF-UHFFFAOYSA-N 2-[2-(2-aminopyrimidin-5-yl)-9-methyl-6-morpholin-4-ylpurin-8-yl]propan-2-ol Chemical compound N1=C2N(C)C(C(C)(C)O)=NC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 YWTFMRUDEJHZGF-UHFFFAOYSA-N 0.000 claims description 6
• XCEDXQNTFRMXPP-UHFFFAOYSA-N 2-[2-(6-aminopyridin-3-yl)-9-methyl-6-morpholin-4-ylpurin-8-yl]propan-2-ol Chemical compound N1=C2N(C)C(C(C)(C)O)=NC2=C(N2CCOCC2)N=C1C1=CC=C(N)N=C1 XCEDXQNTFRMXPP-UHFFFAOYSA-N 0.000 claims description 6
• MAXIMYAATWVVQK-UHFFFAOYSA-N 4-[2-(2-methoxypyrimidin-5-yl)-9-methyl-8-[(4-methylsulfonylpiperazin-1-yl)methyl]purin-6-yl]morpholine Chemical compound C1=NC(OC)=NC=C1C1=NC(N2CCOCC2)=C(N=C(CN2CCN(CC2)S(C)(=O)=O)N2C)C2=N1 MAXIMYAATWVVQK-UHFFFAOYSA-N 0.000 claims description 6
• XLONKHTYYXTLNL-UHFFFAOYSA-N 4-[9-methyl-8-[(4-methylsulfonylpiperazin-1-yl)methyl]-2-pyridin-3-ylpurin-6-yl]morpholine Chemical compound N=1C2=C(N3CCOCC3)N=C(C=3C=NC=CC=3)N=C2N(C)C=1CN1CCN(S(C)(=O)=O)CC1 XLONKHTYYXTLNL-UHFFFAOYSA-N 0.000 claims description 6
• MELXZZULKDAPHV-UHFFFAOYSA-N 5-(9-methyl-6-morpholin-4-ylpurin-2-yl)pyridin-2-amine Chemical compound N1=C2N(C)C=NC2=C(N2CCOCC2)N=C1C1=CC=C(N)N=C1 MELXZZULKDAPHV-UHFFFAOYSA-N 0.000 claims description 6
• RDSWHFASXQEXJX-UHFFFAOYSA-N 5-[6-morpholin-4-yl-9-(2-morpholin-4-ylethyl)purin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(N=CN2CCN3CCOCC3)C2=N1 RDSWHFASXQEXJX-UHFFFAOYSA-N 0.000 claims description 6
• DTUURQKCKMPNGR-UHFFFAOYSA-N 5-[9-[(3-methoxyphenyl)methyl]-6-morpholin-4-ylpurin-2-yl]pyrimidin-2-amine Chemical compound COC1=CC=CC(CN2C3=NC(=NC(=C3N=C2)N2CCOCC2)C=2C=NC(N)=NC=2)=C1 DTUURQKCKMPNGR-UHFFFAOYSA-N 0.000 claims description 6
• KAPWFCMMNVOORR-UHFFFAOYSA-N 5-[9-[(4-methylsulfonylphenyl)methyl]-6-morpholin-4-ylpurin-2-yl]pyrimidin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1CN1C2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2N=C1 KAPWFCMMNVOORR-UHFFFAOYSA-N 0.000 claims description 6
• 229910052739 hydrogen Inorganic materials 0.000 claims description 6
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
• OGLQNIWTBCUNNG-UHFFFAOYSA-N 5-(9-methyl-6-morpholin-4-ylpurin-2-yl)pyrimidin-2-amine Chemical compound N1=C2N(C)C=NC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 OGLQNIWTBCUNNG-UHFFFAOYSA-N 0.000 claims description 5
• KWVCMUVZXMIWLA-UHFFFAOYSA-N 5-[9-methyl-8-[(4-methylsulfonylpiperazin-1-yl)methyl]-6-morpholin-4-ylpurin-2-yl]pyridin-2-amine Chemical compound N=1C2=C(N3CCOCC3)N=C(C=3C=NC(N)=CC=3)N=C2N(C)C=1CN1CCN(S(C)(=O)=O)CC1 KWVCMUVZXMIWLA-UHFFFAOYSA-N 0.000 claims description 5
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
• FDDKQQRYIKXUCV-UHFFFAOYSA-N 2-[2-(2-aminopyrimidin-5-yl)-9-(2-hydroxyethyl)-6-morpholin-4-ylpurin-8-yl]propan-2-ol Chemical compound N1=C2N(CCO)C(C(C)(O)C)=NC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 FDDKQQRYIKXUCV-UHFFFAOYSA-N 0.000 claims description 3
• 230000001028 anti-proliverative effect Effects 0.000 claims description 2
• KSQHFCOCMGKFHC-UHFFFAOYSA-N n-[1-[[2-(2-aminopyrimidin-5-yl)-9-ethyl-6-morpholin-4-ylpurin-8-yl]methyl]piperidin-4-yl]-n-methylmethanesulfonamide Chemical compound N=1C2=C(N3CCOCC3)N=C(C=3C=NC(N)=NC=3)N=C2N(CC)C=1CN1CCC(N(C)S(C)(=O)=O)CC1 KSQHFCOCMGKFHC-UHFFFAOYSA-N 0.000 claims description 2
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 6
• 125000004411 C5-C6 heterocyclyl group Chemical group 0.000 claims 5
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 4
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 1
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 1
• DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims 1
• 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 1
• 235000019260 propionic acid Nutrition 0.000 claims 1
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 51
• 201000010099 disease Diseases 0.000 abstract description 43
• 206010028980 Neoplasm Diseases 0.000 abstract description 37
• 201000011510 cancer Diseases 0.000 abstract description 32
• 230000000694 effects Effects 0.000 abstract description 25
• 238000011282 treatment Methods 0.000 abstract description 23
• 239000000126 substance Substances 0.000 abstract description 21
• 108091007960 PI3Ks Proteins 0.000 abstract description 16
• 125000004429 atom Chemical group 0.000 abstract description 10
• 239000003112 inhibitor Substances 0.000 abstract description 8
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 5
• 108091000080 Phosphotransferase Proteins 0.000 abstract description 4
• 102000020233 phosphotransferase Human genes 0.000 abstract description 4
• 102000001708 Protein Isoforms Human genes 0.000 abstract description 3
• 108010029485 Protein Isoforms Proteins 0.000 abstract description 3
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 abstract description 2
• 230000002062 proliferating effect Effects 0.000 abstract description 2
• 102000038030 PI3Ks Human genes 0.000 abstract 1
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
• 150000003222 pyridines Chemical class 0.000 abstract 1
• 239000000203 mixture Substances 0.000 description 112
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• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 37
• 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 description 36
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