JP2010533715A - 複素環系ｐｋｂ調節剤 - Google Patents

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Publication number

JP2010533715A

JP2010533715A JP2010517014A JP2010517014A JP2010533715A JP 2010533715 A JP2010533715 A JP 2010533715A JP 2010517014 A JP2010517014 A JP 2010517014A JP 2010517014 A JP2010517014 A JP 2010517014A JP 2010533715 A JP2010533715 A JP 2010533715A

Authority

JP

Japan

Prior art keywords

alkyl

compound

formula

aryl

phenyl

Prior art date

2007-07-17

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.)

Withdrawn

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• 125000000623 heterocyclic group Chemical group 0.000 title claims description 43
• 150000001875 compounds Chemical class 0.000 claims abstract description 364
• 239000000203 mixture Substances 0.000 claims abstract description 221
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 72
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 61
• 201000011510 cancer Diseases 0.000 claims abstract description 47
• 201000010099 disease Diseases 0.000 claims abstract description 39
• 230000001404 mediated effect Effects 0.000 claims abstract description 21
• 230000002159 abnormal effect Effects 0.000 claims abstract description 13
• 230000004663 cell proliferation Effects 0.000 claims abstract description 12
• 206010061218 Inflammation Diseases 0.000 claims abstract description 10
• 230000004054 inflammatory process Effects 0.000 claims abstract description 10
• 208000030159 metabolic disease Diseases 0.000 claims abstract description 9
• -1 methoxymethoxy Chemical group 0.000 claims description 333
• 125000003118 aryl group Chemical group 0.000 claims description 108
• 238000000034 method Methods 0.000 claims description 97
• 229910052799 carbon Inorganic materials 0.000 claims description 60
• 229910052739 hydrogen Inorganic materials 0.000 claims description 49
• 239000003814 drug Substances 0.000 claims description 47
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 46
• 125000000217 alkyl group Chemical group 0.000 claims description 42
• 239000008194 pharmaceutical composition Substances 0.000 claims description 35
• 238000011282 treatment Methods 0.000 claims description 35
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 33
• 208000035475 disorder Diseases 0.000 claims description 33
• 150000003839 salts Chemical class 0.000 claims description 32
• 125000001072 heteroaryl group Chemical group 0.000 claims description 31
• 229910052760 oxygen Inorganic materials 0.000 claims description 31
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
• 229910052717 sulfur Inorganic materials 0.000 claims description 25
• 229940124597 therapeutic agent Drugs 0.000 claims description 25
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
• 229910052757 nitrogen Inorganic materials 0.000 claims description 22
• 125000005843 halogen group Chemical group 0.000 claims description 21
• 125000005842 heteroatom Chemical group 0.000 claims description 20
• 241000124008 Mammalia Species 0.000 claims description 19
• 108091000080 Phosphotransferase Proteins 0.000 claims description 18
• 102000020233 phosphotransferase Human genes 0.000 claims description 18
• 125000004076 pyridyl group Chemical group 0.000 claims description 18
• 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 17
• 125000002837 carbocyclic group Chemical group 0.000 claims description 15
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
• 125000001424 substituent group Chemical group 0.000 claims description 15
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
• 125000001624 naphthyl group Chemical group 0.000 claims description 11
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
• 238000004519 manufacturing process Methods 0.000 claims description 10
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 9
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 9
• 125000001041 indolyl group Chemical group 0.000 claims description 9
• 125000006413 ring segment Chemical group 0.000 claims description 9
• 125000001544 thienyl group Chemical group 0.000 claims description 9
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 9
• 230000008878 coupling Effects 0.000 claims description 8
• 238000010168 coupling process Methods 0.000 claims description 8
• 238000005859 coupling reaction Methods 0.000 claims description 8
• 230000005764 inhibitory process Effects 0.000 claims description 8
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
• 206010012601 diabetes mellitus Diseases 0.000 claims description 7
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 6
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
• 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims description 6
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
• 101100481408 Danio rerio tie2 gene Proteins 0.000 claims description 6
• 230000012010 growth Effects 0.000 claims description 6
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 6
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
• 101100481410 Mus musculus Tek gene Proteins 0.000 claims description 5
• 208000016097 disease of metabolism Diseases 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 5
• 229910052700 potassium Inorganic materials 0.000 claims description 5
• 108060006662 GSK3 Proteins 0.000 claims description 4
• 102000001267 GSK3 Human genes 0.000 claims description 4
• 101001064870 Homo sapiens Lon protease homolog, mitochondrial Proteins 0.000 claims description 4
• 101000669921 Homo sapiens Rho-associated protein kinase 2 Proteins 0.000 claims description 4
• 101000595531 Homo sapiens Serine/threonine-protein kinase pim-1 Proteins 0.000 claims description 4
• 101001001648 Homo sapiens Serine/threonine-protein kinase pim-2 Proteins 0.000 claims description 4
• 102100039314 Rho-associated protein kinase 2 Human genes 0.000 claims description 4
• 102100036077 Serine/threonine-protein kinase pim-1 Human genes 0.000 claims description 4
• 102100036120 Serine/threonine-protein kinase pim-2 Human genes 0.000 claims description 4
• 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 4
• 125000001246 bromo group Chemical group Br* 0.000 claims description 4
• 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 4
• 125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 claims description 4
• 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 claims description 4
• 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 claims description 4
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
• 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 4
• NFVJNJQRWPQVOA-UHFFFAOYSA-N n-[2-chloro-5-(trifluoromethyl)phenyl]-2-[3-(4-ethyl-5-ethylsulfanyl-1,2,4-triazol-3-yl)piperidin-1-yl]acetamide Chemical compound CCN1C(SCC)=NN=C1C1CN(CC(=O)NC=2C(=CC=C(C=2)C(F)(F)F)Cl)CCC1 NFVJNJQRWPQVOA-UHFFFAOYSA-N 0.000 claims description 4
• YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 claims description 4
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 4
• 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 4
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 4
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 4
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 3
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 3
• 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 3
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 3
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 3
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 3
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 3
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
• 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 3
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 3
• 108091007914 CDKs Proteins 0.000 claims description 3
• 102100035427 Forkhead box protein O1 Human genes 0.000 claims description 3
• 101000877727 Homo sapiens Forkhead box protein O1 Proteins 0.000 claims description 3
• 108010001127 Insulin Receptor Proteins 0.000 claims description 3
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 3
• 125000002541 furyl group Chemical group 0.000 claims description 3
• 125000002971 oxazolyl group Chemical group 0.000 claims description 3
• 125000004043 oxo group Chemical group O=* 0.000 claims description 3
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
• 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 3
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 3
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
• 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 claims description 2
• 102000003746 Insulin Receptor Human genes 0.000 claims 1
• 108091008611 Protein Kinase B Proteins 0.000 abstract description 57
• 230000001225 therapeutic effect Effects 0.000 abstract description 9
• 102000005765 Proto-Oncogene Proteins c-akt Human genes 0.000 abstract description 3
• 150000002391 heterocyclic compounds Chemical class 0.000 abstract description 3
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 283
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 192
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 179
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 113
• 239000007787 solid Substances 0.000 description 113
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 111
• 239000000047 product Substances 0.000 description 109
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 92
• 235000019439 ethyl acetate Nutrition 0.000 description 89
• 239000000243 solution Substances 0.000 description 83
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 75
• 238000005481 NMR spectroscopy Methods 0.000 description 72
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 71
• 239000000741 silica gel Substances 0.000 description 62
• 229910002027 silica gel Inorganic materials 0.000 description 62
• 102100033810 RAC-alpha serine/threonine-protein kinase Human genes 0.000 description 56
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 56
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 55
• 238000006243 chemical reaction Methods 0.000 description 51
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• 239000002904 solvent Substances 0.000 description 42
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 41
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 38
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