JP2009530233A - Ｐｉ−３キナーゼインヒビターおよびそれらの使用方法 - Google Patents
Ｐｉ−３キナーゼインヒビターおよびそれらの使用方法 Download PDFInfo
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- JP2009530233A JP2009530233A JP2008555474A JP2008555474A JP2009530233A JP 2009530233 A JP2009530233 A JP 2009530233A JP 2008555474 A JP2008555474 A JP 2008555474A JP 2008555474 A JP2008555474 A JP 2008555474A JP 2009530233 A JP2009530233 A JP 2009530233A
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- Prior art keywords
- substituted
- alkyl
- amino
- group
- alkoxy
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- 238000000034 method Methods 0.000 title claims description 200
- 239000002935 phosphatidylinositol 3 kinase inhibitor Substances 0.000 title description 2
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- 150000003905 phosphatidylinositols Chemical class 0.000 claims abstract description 10
- -1 amino, substituted amino Chemical group 0.000 claims description 255
- 125000000623 heterocyclic group Chemical group 0.000 claims description 193
- 125000000217 alkyl group Chemical group 0.000 claims description 144
- 125000001072 heteroaryl group Chemical group 0.000 claims description 144
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- 125000003118 aryl group Chemical group 0.000 claims description 76
- 125000003545 alkoxy group Chemical group 0.000 claims description 72
- 125000003107 substituted aryl group Chemical group 0.000 claims description 69
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 60
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 58
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 43
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
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- 229910052717 sulfur Inorganic materials 0.000 claims description 29
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 26
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- 125000003282 alkyl amino group Chemical group 0.000 claims description 23
- 125000002252 acyl group Chemical group 0.000 claims description 22
- 125000004442 acylamino group Chemical group 0.000 claims description 22
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 21
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- 239000000758 substrate Substances 0.000 claims description 16
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- 238000006366 phosphorylation reaction Methods 0.000 claims description 15
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 14
- 230000000694 effects Effects 0.000 claims description 14
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 125000004423 acyloxy group Chemical group 0.000 claims description 11
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
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- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
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- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 206010020751 Hypersensitivity Diseases 0.000 claims description 4
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 4
- 150000003907 phosphatidylinositol monophosphates Chemical class 0.000 claims description 4
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- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
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- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims description 2
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
- KYRMPMCAOPMOIR-UHFFFAOYSA-N 5-ethyl-2h-tetrazole Chemical compound CCC=1N=NNN=1 KYRMPMCAOPMOIR-UHFFFAOYSA-N 0.000 claims description 2
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- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 235000011180 diphosphates Nutrition 0.000 claims description 2
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 235000020824 obesity Nutrition 0.000 claims description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000005936 piperidyl group Chemical group 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 208000037803 restenosis Diseases 0.000 claims description 2
- 230000036303 septic shock Effects 0.000 claims description 2
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 241001024304 Mino Species 0.000 claims 2
- HKWJHKSHEWVOSS-OMDJCSNQSA-N 1,2-dihexadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol-3,4-bisphosphate) Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCCCCCCCCCC)COP(O)(=O)O[C@H]1[C@H](O)[C@@H](O)[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H]1O HKWJHKSHEWVOSS-OMDJCSNQSA-N 0.000 claims 1
- HELHRENMAVTJOS-UHFFFAOYSA-N N-bromo-1-chloromethanamine Chemical compound [H]C([H])(Cl)NBr HELHRENMAVTJOS-UHFFFAOYSA-N 0.000 claims 1
- WSLBJQQQZZTFBA-MLUQOLBVSA-N PIP[4'](17:0/20:4(5Z,8Z,11Z,14Z)) Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCC)COP(O)(=O)OC1C(O)C(O)C(OP(O)(O)=O)[C@@H](O)C1O WSLBJQQQZZTFBA-MLUQOLBVSA-N 0.000 claims 1
- UBXIJOJXUFYNRG-MPJQEMCDSA-N PIP[5'](17:0/20:4(5Z,8Z,11Z,14Z)) Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCC)COP(O)(=O)O[C@@H]1C(O)[C@H](O)C(O)C(OP(O)(O)=O)C1O UBXIJOJXUFYNRG-MPJQEMCDSA-N 0.000 claims 1
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- 201000010099 disease Diseases 0.000 abstract description 24
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- 239000003102 growth factor Substances 0.000 abstract description 3
- 150000003904 phospholipids Chemical class 0.000 abstract description 3
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- 108010008959 G-Protein-Coupled Receptor Kinases Proteins 0.000 abstract 1
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 195
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- 239000000243 solution Substances 0.000 description 81
- 125000000392 cycloalkenyl group Chemical group 0.000 description 78
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- 238000002360 preparation method Methods 0.000 description 71
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 62
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 37
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- 238000006243 chemical reaction Methods 0.000 description 37
- 239000012267 brine Substances 0.000 description 34
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 34
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 28
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- 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 description 16
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| PCT/US2007/062157 WO2007095588A1 (en) | 2006-02-14 | 2007-02-14 | Pi-3 kinase inhibitors and methods of their use |
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Also Published As
| Publication number | Publication date |
|---|---|
| RU2008136783A (ru) | 2010-03-20 |
| MX2008010397A (es) | 2008-10-27 |
| CA2642738A1 (en) | 2007-08-23 |
| PE20070978A1 (es) | 2007-11-15 |
| WO2007095588A1 (en) | 2007-08-23 |
| AR059506A1 (es) | 2008-04-09 |
| US20100075965A1 (en) | 2010-03-25 |
| EP1989201A1 (en) | 2008-11-12 |
| KR20080112202A (ko) | 2008-12-24 |
| TW200804379A (en) | 2008-01-16 |
| AU2007214462A1 (en) | 2007-08-23 |
| BRPI0707816A2 (pt) | 2011-05-10 |
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