JP5261575B2 - 化学化合物 - Google Patents

Info

Publication number

JP5261575B2

JP5261575B2 JP2011515631A JP2011515631A JP5261575B2 JP 5261575 B2 JP5261575 B2 JP 5261575B2 JP 2011515631 A JP2011515631 A JP 2011515631A JP 2011515631 A JP2011515631 A JP 2011515631A JP 5261575 B2 JP5261575 B2 JP 5261575B2

Authority

JP

Japan

Prior art keywords

thiazolidine

dione

phenyl

methylidene

methyl

Prior art date

2008-07-02

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.)

Expired - Fee Related

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• 150000001875 compounds Chemical class 0.000 title claims description 122
• 150000003839 salts Chemical class 0.000 claims description 61
• 101000595531 Homo sapiens Serine/threonine-protein kinase pim-1 Proteins 0.000 claims description 29
• 206010028980 Neoplasm Diseases 0.000 claims description 29
• 102100036077 Serine/threonine-protein kinase pim-1 Human genes 0.000 claims description 29
• 201000011510 cancer Diseases 0.000 claims description 25
• 239000008194 pharmaceutical composition Substances 0.000 claims description 20
• 101001001642 Xenopus laevis Serine/threonine-protein kinase pim-3 Proteins 0.000 claims description 7
• 238000011282 treatment Methods 0.000 claims description 7
• 101100297652 Coturnix japonica PIM3 gene Proteins 0.000 claims description 5
• 101100297651 Mus musculus Pim2 gene Proteins 0.000 claims description 5
• 206010060862 Prostate cancer Diseases 0.000 claims description 4
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 4
• 230000002401 inhibitory effect Effects 0.000 claims description 4
• 206010025323 Lymphomas Diseases 0.000 claims description 3
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 3
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 3
• 201000002528 pancreatic cancer Diseases 0.000 claims description 3
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 3
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
• 208000032839 leukemia Diseases 0.000 claims description 2
• 239000003085 diluting agent Substances 0.000 claims 1
• 239000003937 drug carrier Substances 0.000 claims 1
• -1 nitro, cyano, hydroxy, amino, mercapto, formyl Chemical group 0.000 description 509
• 125000000217 alkyl group Chemical group 0.000 description 97
• 238000000034 method Methods 0.000 description 91
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 67
• 239000000203 mixture Substances 0.000 description 67
• 125000003118 aryl group Chemical group 0.000 description 55
• 229910052736 halogen Inorganic materials 0.000 description 53
• 150000002367 halogens Chemical class 0.000 description 52
• 125000000623 heterocyclic group Chemical group 0.000 description 50
• 150000002431 hydrogen Chemical class 0.000 description 49
• 125000004452 carbocyclyl group Chemical group 0.000 description 46
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 38
• 239000001257 hydrogen Substances 0.000 description 37
• 229910052739 hydrogen Inorganic materials 0.000 description 37
• 125000003545 alkoxy group Chemical group 0.000 description 29
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 28
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
• 239000007858 starting material Substances 0.000 description 27
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 25
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 23
• 235000019439 ethyl acetate Nutrition 0.000 description 23
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
• 238000003756 stirring Methods 0.000 description 22
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 21
• 229910052757 nitrogen Inorganic materials 0.000 description 20
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 20
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
• 125000004391 aryl sulfonyl group Chemical group 0.000 description 19
• 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 description 18
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 18
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
• 238000006243 chemical reaction Methods 0.000 description 18
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 18
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 18
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 18
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 17
• 125000006125 ethylsulfonyl group Chemical group 0.000 description 17
• 239000003112 inhibitor Substances 0.000 description 17
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 17
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 17
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 16
• 238000005481 NMR spectroscopy Methods 0.000 description 16
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 16
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 16
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 15
• 239000007787 solid Substances 0.000 description 15
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
• 125000001589 carboacyl group Chemical group 0.000 description 13
• 125000004432 carbon atom Chemical group C* 0.000 description 13
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 12
• ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 12
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
• 238000002156 mixing Methods 0.000 description 12
• 239000000047 product Substances 0.000 description 12
• 229910052760 oxygen Inorganic materials 0.000 description 11
• 238000010898 silica gel chromatography Methods 0.000 description 11
• 229910052717 sulfur Inorganic materials 0.000 description 11
• 238000013459 approach Methods 0.000 description 10
• 239000000543 intermediate Substances 0.000 description 10
• 239000000243 solution Substances 0.000 description 10
• 239000003795 chemical substances by application Substances 0.000 description 9
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 8
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
• 125000005153 alkyl sulfamoyl group Chemical group 0.000 description 8
• 238000004519 manufacturing process Methods 0.000 description 8
• 239000011541 reaction mixture Substances 0.000 description 8
• 229920006395 saturated elastomer Polymers 0.000 description 8
• 239000011734 sodium Substances 0.000 description 8
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 8
• QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 7
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 7
• 101001064870 Homo sapiens Lon protease homolog, mitochondrial Proteins 0.000 description 7
• 239000000284 extract Substances 0.000 description 7
• 238000004007 reversed phase HPLC Methods 0.000 description 7
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 7
• ZKHQWZAMYRWXGA-KQYNXXCUSA-J ATP(4-) Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-J 0.000 description 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
• ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 6
• 238000003556 assay Methods 0.000 description 6
• 239000000872 buffer Substances 0.000 description 6
• 238000004587 chromatography analysis Methods 0.000 description 6
• 230000000694 effects Effects 0.000 description 6
• 239000003480 eluent Substances 0.000 description 6
• 150000002148 esters Chemical class 0.000 description 6
• 239000000706 filtrate Substances 0.000 description 6
• 125000001072 heteroaryl group Chemical group 0.000 description 6
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 6
• 230000002265 prevention Effects 0.000 description 6
• 238000010992 reflux Methods 0.000 description 6
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 5
• 102000004190 Enzymes Human genes 0.000 description 5
• 108090000790 Enzymes Proteins 0.000 description 5
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
• 102000001253 Protein Kinase Human genes 0.000 description 5
• 201000010099 disease Diseases 0.000 description 5
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
• 239000003814 drug Substances 0.000 description 5
• 229940088598 enzyme Drugs 0.000 description 5
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 5
• 238000000338 in vitro Methods 0.000 description 5
• 125000002950 monocyclic group Chemical group 0.000 description 5
• 229960005419 nitrogen Drugs 0.000 description 5
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
• 230000026731 phosphorylation Effects 0.000 description 5
• 238000006366 phosphorylation reaction Methods 0.000 description 5
• 239000000725 suspension Substances 0.000 description 5
• ZLDXTUTZYPVCKG-VPMLRQHESA-N (5z)-5-[[2-[(3r)-3-aminopiperidin-1-yl]-3-chlorophenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](N)CCCN1C1=C(Cl)C=CC=C1\C=C/1C(=O)NC(=O)S\1 ZLDXTUTZYPVCKG-VPMLRQHESA-N 0.000 description 4
• MAXWYVPUCAYEHZ-ZSOIEALJSA-N (5z)-5-[[5-amino-2-[3-(dimethylamino)pyrrolidin-1-yl]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1C(N(C)C)CCN1C1=CC=C(N)C=C1\C=C/1C(=O)NC(=O)S\1 MAXWYVPUCAYEHZ-ZSOIEALJSA-N 0.000 description 4
• VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
• JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 4
• SYFAMQSVMVHCIS-NSHDSACASA-N 3-bromo-2-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]benzaldehyde Chemical compound C1[C@@H](N(C)C)CCN1C1=C(Br)C=CC=C1C=O SYFAMQSVMVHCIS-NSHDSACASA-N 0.000 description 4
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
• 102000004127 Cytokines Human genes 0.000 description 4
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• AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 4
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 4
• 239000007995 HEPES buffer Substances 0.000 description 4
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
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• BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 description 4
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• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 4
• VWJNQFFHSJTVGQ-CJAAZZPWSA-N n-[(3s)-1-[2-chloro-6-[(z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenyl]pyrrolidin-3-yl]-1-methylimidazole-2-carboxamide Chemical compound CN1C=CN=C1C(=O)N[C@@H]1CN(C=2C(=CC=CC=2Cl)\C=C/2C(NC(=O)S\2)=O)CC1 VWJNQFFHSJTVGQ-CJAAZZPWSA-N 0.000 description 4
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• MCUJKPPARUPFJM-UWCCDQBKSA-N (5z)-5-[[2-[(3r)-3-aminopiperidin-1-yl]-3-phenylphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](N)CCCN1C(C(=CC=C1)C=2C=CC=CC=2)=C1\C=C/1C(=O)NC(=O)S\1 MCUJKPPARUPFJM-UWCCDQBKSA-N 0.000 description 3
• STVUNYMVAGCJLS-OKSBFYSISA-N (5z)-5-[[3-chloro-2-[(3r)-3-(dipropylamino)piperidin-1-yl]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](N(CCC)CCC)CCCN1C1=C(Cl)C=CC=C1\C=C/1C(=O)NC(=O)S\1 STVUNYMVAGCJLS-OKSBFYSISA-N 0.000 description 3
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 3
• ROQSCVKICOMOQP-UHFFFAOYSA-N 5-[(2-morpholin-4-yl-5-nitrophenyl)methylidene]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1=CC1=CC([N+](=O)[O-])=CC=C1N1CCOCC1 ROQSCVKICOMOQP-UHFFFAOYSA-N 0.000 description 3
• HFCDVSYUOXEJNS-UHFFFAOYSA-N 5-[[2-(2,6-dichloro-3-methylanilino)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound CC1=CC=C(Cl)C(NC=2C(=CC=CC=2)C=C2C(NC(=O)S2)=O)=C1Cl HFCDVSYUOXEJNS-UHFFFAOYSA-N 0.000 description 3
• CWZULMCFFVJFEY-UHFFFAOYSA-N 5-[[2-(4-methylpiperazin-1-yl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1CN(C)CCN1C1=CC=CC=C1C=C1C(=O)NC(=O)S1 CWZULMCFFVJFEY-UHFFFAOYSA-N 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
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• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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• 125000004429 atom Chemical group 0.000 description 3
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• 238000002512 chemotherapy Methods 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
• 125000004663 dialkyl amino group Chemical group 0.000 description 3
• YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 3
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• AAKJLRGGTJKAMG-UHFFFAOYSA-N erlotinib Chemical compound C=12C=C(OCCOC)C(OCCOC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 AAKJLRGGTJKAMG-UHFFFAOYSA-N 0.000 description 3
• 125000005842 heteroatom Chemical group 0.000 description 3
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• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
• 125000001424 substituent group Chemical group 0.000 description 3
• 238000002560 therapeutic procedure Methods 0.000 description 3
• 125000003396 thiol group Chemical class [H]S* 0.000 description 3
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