JP2007514639A - 少なくとも１の他の抗癌剤と組み合わせた少なくとも１のＣｄｃ２５ホスファターゼ阻害剤を含有する製品 - Google Patents

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Publication number

JP2007514639A

JP2007514639A JP2006516322A JP2006516322A JP2007514639A JP 2007514639 A JP2007514639 A JP 2007514639A JP 2006516322 A JP2006516322 A JP 2006516322A JP 2006516322 A JP2006516322 A JP 2006516322A JP 2007514639 A JP2007514639 A JP 2007514639A

Authority

JP

Japan

Prior art keywords

group

alkyl

amino

groups

independently

Prior art date

2003-06-25

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.)

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• 102000007588 cdc25 Phosphatases Human genes 0.000 title claims abstract description 68
• 108010046616 cdc25 Phosphatases Proteins 0.000 title claims abstract description 68
• 229940122907 Phosphatase inhibitor Drugs 0.000 title claims abstract description 56
• 229940127084 other anti-cancer agent Drugs 0.000 title claims abstract description 11
• 150000001875 compounds Chemical class 0.000 claims abstract description 221
• 210000004027 cell Anatomy 0.000 claims abstract description 51
• 239000002246 antineoplastic agent Substances 0.000 claims abstract description 48
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 31
• 239000003112 inhibitor Substances 0.000 claims abstract description 20
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 18
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 14
• 102000003903 Cyclin-dependent kinases Human genes 0.000 claims abstract description 13
• 108090000266 Cyclin-dependent kinases Proteins 0.000 claims abstract description 13
• 201000011510 cancer Diseases 0.000 claims abstract description 12
• 230000001225 therapeutic effect Effects 0.000 claims abstract description 8
• 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 6
• 239000003534 dna topoisomerase inhibitor Substances 0.000 claims abstract description 6
• 229940044693 topoisomerase inhibitor Drugs 0.000 claims abstract description 6
• 102000034345 heterotrimeric G proteins Human genes 0.000 claims abstract description 5
• 108091006093 heterotrimeric G proteins Proteins 0.000 claims abstract description 5
• 230000019491 signal transduction Effects 0.000 claims abstract description 5
• 230000006820 DNA synthesis Effects 0.000 claims abstract description 3
• 230000002152 alkylating effect Effects 0.000 claims abstract description 3
• 230000032823 cell division Effects 0.000 claims abstract description 3
• 210000004292 cytoskeleton Anatomy 0.000 claims abstract description 3
• 229940121659 Prenyltransferase inhibitor Drugs 0.000 claims abstract 4
• 125000000217 alkyl group Chemical group 0.000 claims description 353
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 145
• 125000003118 aryl group Chemical group 0.000 claims description 128
• -1 cyano, amino Chemical group 0.000 claims description 119
• 125000005843 halogen group Chemical group 0.000 claims description 106
• 125000000623 heterocyclic group Chemical group 0.000 claims description 106
• 125000003545 alkoxy group Chemical group 0.000 claims description 102
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 83
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 63
• 125000001188 haloalkyl group Chemical group 0.000 claims description 58
• 150000003839 salts Chemical class 0.000 claims description 58
• 125000001424 substituent group Chemical group 0.000 claims description 58
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 46
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 41
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical group FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 41
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 39
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 38
• 229910052757 nitrogen Inorganic materials 0.000 claims description 38
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 37
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 34
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
• 125000005842 heteroatom Chemical group 0.000 claims description 30
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 26
• 125000004414 alkyl thio group Chemical group 0.000 claims description 25
• 125000001072 heteroaryl group Chemical group 0.000 claims description 24
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 23
• 125000002837 carbocyclic group Chemical group 0.000 claims description 21
• 125000004432 carbon atom Chemical group C* 0.000 claims description 21
• 229910052760 oxygen Inorganic materials 0.000 claims description 21
• 229910052717 sulfur Inorganic materials 0.000 claims description 21
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 20
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 20
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• 125000004438 haloalkoxy group Chemical group 0.000 claims description 17
• 125000003282 alkyl amino group Chemical group 0.000 claims description 15
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 13
• 125000003342 alkenyl group Chemical group 0.000 claims description 11
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 10
• 150000001721 carbon Chemical class 0.000 claims description 10
• 125000004122 cyclic group Chemical group 0.000 claims description 10
• 238000004519 manufacturing process Methods 0.000 claims description 10
• 125000000304 alkynyl group Chemical group 0.000 claims description 9
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 9
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
• 125000004076 pyridyl group Chemical group 0.000 claims description 9
• MJVAVZPDRWSRRC-UHFFFAOYSA-N vitamin K3 Natural products C1=CC=C2C(=O)C(C)=CC(=O)C2=C1 MJVAVZPDRWSRRC-UHFFFAOYSA-N 0.000 claims description 9
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
• 125000002947 alkylene group Chemical group 0.000 claims description 8
• VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical group C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 claims description 8
• 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 8
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 8
• GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical compound N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 claims description 7
• 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 7
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
• 125000003277 amino group Chemical group 0.000 claims description 7
• WCUXJAHSNPROCI-UHFFFAOYSA-N 2-(2-chloro-6-fluorophenyl)-5-[2-(dimethylamino)ethylamino]-1,3-benzothiazole-4,7-dione Chemical compound N=1C=2C(=O)C(NCCN(C)C)=CC(=O)C=2SC=1C1=C(F)C=CC=C1Cl WCUXJAHSNPROCI-UHFFFAOYSA-N 0.000 claims description 6
• KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 claims description 6
• 229940127093 camptothecin Drugs 0.000 claims description 6
• 229910052799 carbon Inorganic materials 0.000 claims description 6
• 229940043378 cyclin-dependent kinase inhibitor Drugs 0.000 claims description 6
• VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 claims description 6
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 6
• 125000002757 morpholinyl group Chemical group 0.000 claims description 6
• 125000004193 piperazinyl group Chemical group 0.000 claims description 6
• BTIHMVBBUGXLCJ-OAHLLOKOSA-N seliciclib Chemical group C=12N=CN(C(C)C)C2=NC(N[C@@H](CO)CC)=NC=1NCC1=CC=CC=C1 BTIHMVBBUGXLCJ-OAHLLOKOSA-N 0.000 claims description 6
• 125000001544 thienyl group Chemical group 0.000 claims description 6
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 6
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
• 125000002541 furyl group Chemical group 0.000 claims description 5
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
• 239000003528 protein farnesyltransferase inhibitor Substances 0.000 claims description 5
• 125000004953 trihalomethyl group Chemical group 0.000 claims description 5
• 235000012711 vitamin K3 Nutrition 0.000 claims description 5
• 239000011652 vitamin K3 Substances 0.000 claims description 5
• 229940124226 Farnesyltransferase inhibitor Drugs 0.000 claims description 4
• 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 4
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 4
• 239000002875 cyclin dependent kinase inhibitor Substances 0.000 claims description 4
• 125000005366 cycloalkylthio group Chemical group 0.000 claims description 4
• 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 4
• 229910052736 halogen Inorganic materials 0.000 claims description 4
• 150000002367 halogens Chemical class 0.000 claims description 4
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 4
• 125000002883 imidazolyl group Chemical group 0.000 claims description 4
• 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 claims description 4
• 229940041603 vitamin k 3 Drugs 0.000 claims description 4
• SGAOXTHFXVLOBH-KRWDZBQOSA-N (8s)-8-(cyclohexylmethyl)-2-phenyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine Chemical compound C([C@H]1C2=NC(=CN2CCN1)C=1C=CC=CC=1)C1CCCCC1 SGAOXTHFXVLOBH-KRWDZBQOSA-N 0.000 claims description 3
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 3
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
• MTUYOFGUEXWKLC-UHFFFAOYSA-N 5-[2-(dimethylamino)ethylamino]-2-methyl-1,3-benzothiazole-4,7-dione Chemical compound O=C1C(NCCN(C)C)=CC(=O)C2=C1N=C(C)S2 MTUYOFGUEXWKLC-UHFFFAOYSA-N 0.000 claims description 3
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 3
• 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 3
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 3
• JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 3
• 125000001624 naphthyl group Chemical group 0.000 claims description 3
• 239000001301 oxygen Substances 0.000 claims description 3
• 239000002798 polar solvent Substances 0.000 claims description 3
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• 125000000335 thiazolyl group Chemical group 0.000 claims description 3
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
• GNYQLPKGXMSQNY-UHFFFAOYSA-N 2-methyl-5-(2-piperidin-1-ylethylamino)-1,3-benzothiazole-4,7-dione Chemical compound S1C(C)=NC(C2=O)=C1C(=O)C=C2NCCN1CCCCC1 GNYQLPKGXMSQNY-UHFFFAOYSA-N 0.000 claims description 2
• LSDWHZYIIRIPCU-UHFFFAOYSA-N 2-methyl-5-(2-pyrrolidin-1-ylethylamino)-1,3-benzothiazole-4,7-dione Chemical compound S1C(C)=NC(C2=O)=C1C(=O)C=C2NCCN1CCCC1 LSDWHZYIIRIPCU-UHFFFAOYSA-N 0.000 claims description 2
• 125000004638 2-oxopiperazinyl group Chemical group O=C1N(CCNC1)* 0.000 claims description 2
• 125000004637 2-oxopiperidinyl group Chemical group O=C1N(CCCC1)* 0.000 claims description 2
• 150000001408 amides Chemical class 0.000 claims description 2
• 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 2
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• 125000004104 aryloxy group Chemical group 0.000 claims description 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
• 125000002785 azepinyl group Chemical group 0.000 claims description 2
• 150000001540 azides Chemical class 0.000 claims description 2
• 125000005335 azido alkyl group Chemical group 0.000 claims description 2
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
• 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
• 125000004601 benzofurazanyl group Chemical group N1=C2C(=NO1)C(=CC=C2)* 0.000 claims description 2
• 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
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• 239000000539 dimer Substances 0.000 claims description 2
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• LFQCJSBXBZRMTN-OAQYLSRUSA-N diflomotecan Chemical compound CC[C@@]1(O)CC(=O)OCC(C2=O)=C1C=C1N2CC2=CC3=CC(F)=C(F)C=C3N=C21 LFQCJSBXBZRMTN-OAQYLSRUSA-N 0.000 claims 1
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