KR20070052309A - 키나제 억제제인 비시클릭 아미드 - Google Patents

Info

Publication number

KR20070052309A

KR20070052309A KR1020077005959A KR20077005959A KR20070052309A KR 20070052309 A KR20070052309 A KR 20070052309A KR 1020077005959 A KR1020077005959 A KR 1020077005959A KR 20077005959 A KR20077005959 A KR 20077005959A KR 20070052309 A KR20070052309 A KR 20070052309A

Authority

KR

South Korea

Prior art keywords

mmol

lower alkyl

carboxylic acid

amino

etoac

Prior art date

2004-09-15

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

• Espacenet
• Global Dossier
• Discuss

• -1 Bicyclic Amides Chemical class 0.000 title claims abstract description 124
• 229940043355 kinase inhibitor Drugs 0.000 title description 5
• 239000003757 phosphotransferase inhibitor Substances 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 335
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 59
• 201000010099 disease Diseases 0.000 claims abstract description 53
• 102000001253 Protein Kinase Human genes 0.000 claims abstract description 33
• 108060006633 protein kinase Proteins 0.000 claims abstract description 33
• 230000001419 dependent effect Effects 0.000 claims abstract description 27
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 18
• 230000002062 proliferating effect Effects 0.000 claims abstract description 14
• 241001465754 Metazoa Species 0.000 claims abstract description 11
• 125000000217 alkyl group Chemical group 0.000 claims description 72
• 229910052757 nitrogen Inorganic materials 0.000 claims description 54
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 48
• 150000003839 salts Chemical class 0.000 claims description 46
• 229910052739 hydrogen Inorganic materials 0.000 claims description 32
• 125000005843 halogen group Chemical group 0.000 claims description 30
• 229910052799 carbon Inorganic materials 0.000 claims description 28
• 238000000034 method Methods 0.000 claims description 27
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
• 125000003282 alkyl amino group Chemical group 0.000 claims description 19
• 230000005764 inhibitory process Effects 0.000 claims description 19
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
• 239000001301 oxygen Substances 0.000 claims description 18
• 229910052760 oxygen Inorganic materials 0.000 claims description 18
• 125000001424 substituent group Chemical group 0.000 claims description 17
• 125000003545 alkoxy group Chemical group 0.000 claims description 16
• 238000002360 preparation method Methods 0.000 claims description 16
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
• 125000004432 carbon atom Chemical group C* 0.000 claims description 13
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
• WEVYNIUIFUYDGI-UHFFFAOYSA-N 3-[6-[4-(trifluoromethoxy)anilino]-4-pyrimidinyl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2N=CN=C(NC=3C=CC(OC(F)(F)F)=CC=3)C=2)=C1 WEVYNIUIFUYDGI-UHFFFAOYSA-N 0.000 claims description 11
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
• 125000005842 heteroatom Chemical group 0.000 claims description 10
• 125000000623 heterocyclic group Chemical group 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
• 229910052717 sulfur Inorganic materials 0.000 claims description 10
• 239000011593 sulfur Substances 0.000 claims description 10
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 9
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 9
• 125000003107 substituted aryl group Chemical group 0.000 claims description 9
• 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 claims description 8
• 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 claims description 8
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
• 125000001153 fluoro group Chemical group F* 0.000 claims description 8
• 125000002757 morpholinyl group Chemical group 0.000 claims description 8
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
• 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 7
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
• 108091008606 PDGF receptors Proteins 0.000 claims description 5
• 108010014608 Proto-Oncogene Proteins c-kit Proteins 0.000 claims description 5
• 102000016971 Proto-Oncogene Proteins c-kit Human genes 0.000 claims description 5
• 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• 125000001246 bromo group Chemical group Br* 0.000 claims description 4
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
• 230000000069 prophylactic effect Effects 0.000 claims description 4
• 102100031983 Ephrin type-B receptor 4 Human genes 0.000 claims description 3
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 3
• 125000006630 butoxycarbonylamino group Chemical group 0.000 claims description 3
• 125000004744 butyloxycarbonyl group Chemical group 0.000 claims description 3
• 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 3
• 125000006001 difluoroethyl group Chemical group 0.000 claims description 3
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
• 125000006626 methoxycarbonylamino group Chemical group 0.000 claims description 3
• 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 3
• 230000004044 response Effects 0.000 claims description 3
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
• 239000000203 mixture Substances 0.000 abstract description 124
• 206010028980 Neoplasm Diseases 0.000 abstract description 8
• 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 abstract 1
• 239000003909 protein kinase inhibitor Substances 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 554
• 235000019439 ethyl acetate Nutrition 0.000 description 272
• 239000000243 solution Substances 0.000 description 235
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 221
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 162
• 238000004128 high performance liquid chromatography Methods 0.000 description 125
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 106
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 96
• 239000012267 brine Substances 0.000 description 84
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 84
• 238000004809 thin layer chromatography Methods 0.000 description 77
• 239000011734 sodium Substances 0.000 description 76
• 230000008018 melting Effects 0.000 description 66
• 238000002844 melting Methods 0.000 description 66
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 65
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 62
• 239000012044 organic layer Substances 0.000 description 57
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 54
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
• 239000011541 reaction mixture Substances 0.000 description 51
• 239000008346 aqueous phase Substances 0.000 description 47
• 239000007787 solid Substances 0.000 description 46
• 210000004027 cell Anatomy 0.000 description 44
• 230000000694 effects Effects 0.000 description 42
• 229910004298 SiO 2 Inorganic materials 0.000 description 41
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 38
• 239000000725 suspension Substances 0.000 description 35
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
• 238000004587 chromatography analysis Methods 0.000 description 34
• 238000003756 stirring Methods 0.000 description 34
• 239000000706 filtrate Substances 0.000 description 32
• PAQZWJGSJMLPMG-UHFFFAOYSA-N 2,4,6-tripropyl-1,3,5,2$l^{5},4$l^{5},6$l^{5}-trioxatriphosphinane 2,4,6-trioxide Chemical compound CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 description 31
• 239000007858 starting material Substances 0.000 description 31
• 239000002904 solvent Substances 0.000 description 29
• 108091000080 Phosphotransferase Proteins 0.000 description 28
• 102000020233 phosphotransferase Human genes 0.000 description 28
• 102000004169 proteins and genes Human genes 0.000 description 28
• 108090000623 proteins and genes Proteins 0.000 description 28
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 26
• 238000006243 chemical reaction Methods 0.000 description 25
• 239000000741 silica gel Substances 0.000 description 25
• 229910002027 silica gel Inorganic materials 0.000 description 25
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
• 239000000843 powder Substances 0.000 description 24
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 22
• 230000002829 reductive effect Effects 0.000 description 22
• VIUDTWATMPPKEL-UHFFFAOYSA-N 3-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(F)(F)F)=C1 VIUDTWATMPPKEL-UHFFFAOYSA-N 0.000 description 21
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 21
• 239000010410 layer Substances 0.000 description 20
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• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 18
• 239000003054 catalyst Substances 0.000 description 18
• 230000007423 decrease Effects 0.000 description 18
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
• 239000012071 phase Substances 0.000 description 18
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• 239000012043 crude product Substances 0.000 description 17
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• 229910052731 fluorine Inorganic materials 0.000 description 17
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• 229920006395 saturated elastomer Polymers 0.000 description 16
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
• 239000000047 product Substances 0.000 description 15
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 14
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• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
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• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
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• LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 5
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