OA11352A - Substituted 4-amino-thiazol-2-yl compounds as CDKsinhibitors. - Google Patents

Info

Publication number

OA11352A

OA11352A OA1200000120A OA1200000120A OA11352A OA 11352 A OA11352 A OA 11352A OA 1200000120 A OA1200000120 A OA 1200000120A OA 1200000120 A OA1200000120 A OA 1200000120A OA 11352 A OA11352 A OA 11352A

Authority

OA

OAPI

Prior art keywords

amino

phenyl

fused

calcd

prepared

Prior art date

1997-10-27

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• -1 4-amino-thiazol-2-yl compounds Chemical class 0.000 title claims description 53
• 150000001875 compounds Chemical class 0.000 claims abstract description 245
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 71
• 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 37
• 125000002950 monocyclic group Chemical group 0.000 claims abstract description 33
• 108010025464 Cyclin-Dependent Kinase 4 Proteins 0.000 claims abstract description 29
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 28
• 125000003367 polycyclic group Chemical group 0.000 claims abstract description 28
• 229940002612 prodrug Drugs 0.000 claims abstract description 23
• 239000000651 prodrug Substances 0.000 claims abstract description 23
• 125000001424 substituent group Chemical group 0.000 claims abstract description 23
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims abstract description 22
• 238000000034 method Methods 0.000 claims abstract description 21
• 150000003573 thiols Chemical class 0.000 claims abstract description 19
• 125000003118 aryl group Chemical group 0.000 claims abstract description 17
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 17
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 16
• 150000002148 esters Chemical class 0.000 claims abstract description 15
• 150000002576 ketones Chemical class 0.000 claims abstract description 15
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 15
• 150000003568 thioethers Chemical class 0.000 claims abstract description 15
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 14
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 14
• 150000003839 salts Chemical class 0.000 claims abstract description 14
• 229940124530 sulfonamide Drugs 0.000 claims abstract description 14
• 150000003456 sulfonamides Chemical class 0.000 claims abstract description 14
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 13
• 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 13
• 150000002466 imines Chemical class 0.000 claims abstract description 13
• 125000000394 phosphonato group Chemical group [O-]P([O-])(*)=O 0.000 claims abstract description 13
• 125000003368 amide group Chemical group 0.000 claims abstract description 12
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 12
• 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims abstract description 12
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 11
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 11
• 239000001301 oxygen Substances 0.000 claims abstract description 11
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
• 229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract description 11
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
• 150000002367 halogens Chemical class 0.000 claims abstract description 9
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 7
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 5
• 102000016736 Cyclin Human genes 0.000 claims description 55
• 108050006400 Cyclin Proteins 0.000 claims description 55
• 102000013701 Cyclin-Dependent Kinase 4 Human genes 0.000 claims description 28
• 239000003795 chemical substances by application Substances 0.000 claims description 26
• 230000022983 regulation of cell cycle Effects 0.000 claims description 23
• 230000005764 inhibitory process Effects 0.000 claims description 17
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
• 125000000217 alkyl group Chemical group 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 125000001544 thienyl group Chemical class 0.000 claims description 5
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
• 230000001404 mediated effect Effects 0.000 claims description 4
• 125000003545 alkoxy group Chemical group 0.000 claims description 3
• 150000003973 alkyl amines Chemical class 0.000 claims description 3
• 125000004104 aryloxy group Chemical group 0.000 claims description 2
• 201000010099 disease Diseases 0.000 claims description 2
• 108091007914 CDKs Proteins 0.000 abstract description 31
• 108010024986 Cyclin-Dependent Kinase 2 Proteins 0.000 abstract description 22
• 102100036239 Cyclin-dependent kinase 2 Human genes 0.000 abstract description 22
• 206010028980 Neoplasm Diseases 0.000 abstract description 19
• 108010025468 Cyclin-Dependent Kinase 6 Proteins 0.000 abstract description 5
• 102100026804 Cyclin-dependent kinase 6 Human genes 0.000 abstract description 5
• 102000003903 Cyclin-dependent kinases Human genes 0.000 abstract description 5
• 108090000266 Cyclin-dependent kinases Proteins 0.000 abstract description 5
• 230000002401 inhibitory effect Effects 0.000 abstract description 5
• 101710106279 Cyclin-dependent kinase 1 Proteins 0.000 abstract description 4
• 102100032857 Cyclin-dependent kinase 1 Human genes 0.000 abstract description 4
• 230000001225 therapeutic effect Effects 0.000 abstract description 4
• 230000036210 malignancy Effects 0.000 abstract description 3
• 230000000069 prophylactic effect Effects 0.000 abstract description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 6
• 125000006727 (C1-C6) alkenyl group Chemical group 0.000 abstract 3
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 3
• 125000006728 (C1-C6) alkynyl group Chemical group 0.000 abstract 3
• 150000001299 aldehydes Chemical class 0.000 abstract 2
• RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 abstract 1
• 102100036252 Cyclin-dependent kinase 4 Human genes 0.000 abstract 1
• 239000002207 metabolite Substances 0.000 abstract 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 192
• 239000007787 solid Substances 0.000 description 161
• 238000005481 NMR spectroscopy Methods 0.000 description 158
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 111
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 110
• 229910001868 water Inorganic materials 0.000 description 108
• 238000000746 purification Methods 0.000 description 107
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 98
• 238000002000 high resolution fast-atom bombardment mass spectrometry Methods 0.000 description 78
• 239000000203 mixture Substances 0.000 description 74
• 239000000843 powder Substances 0.000 description 65
• 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 52
• 239000000243 solution Substances 0.000 description 45
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
• 239000003921 oil Substances 0.000 description 38
• 235000019198 oils Nutrition 0.000 description 38
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 32
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 30
• 101150041968 CDC13 gene Proteins 0.000 description 28
• 210000004027 cell Anatomy 0.000 description 28
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• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 22
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 18
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
• 239000000725 suspension Substances 0.000 description 16
• IMDUFDNFSJWYQT-UHFFFAOYSA-N 4-isothiocyanatobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(N=C=S)C=C1 IMDUFDNFSJWYQT-UHFFFAOYSA-N 0.000 description 15
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 15
• UZKLFNHMBFDXEN-UHFFFAOYSA-N 2-bromo-1-(2,6-difluorophenyl)ethanone Chemical compound FC1=CC=CC(F)=C1C(=O)CBr UZKLFNHMBFDXEN-UHFFFAOYSA-N 0.000 description 14
• SGXUUCSRVVSMGK-UHFFFAOYSA-N 2-bromo-1-(2-nitrophenyl)ethanone Chemical compound [O-][N+](=O)C1=CC=CC=C1C(=O)CBr SGXUUCSRVVSMGK-UHFFFAOYSA-N 0.000 description 14
• 239000003112 inhibitor Substances 0.000 description 14
• 238000001953 recrystallisation Methods 0.000 description 14
• 239000013078 crystal Substances 0.000 description 13
• 239000012044 organic layer Substances 0.000 description 13
• TXUHKKKUXDGIET-UHFFFAOYSA-N 2-bromo-1-(2-iodophenyl)ethanone Chemical compound BrCC(=O)C1=CC=CC=C1I TXUHKKKUXDGIET-UHFFFAOYSA-N 0.000 description 12
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• 229910004373 HOAc Inorganic materials 0.000 description 12
• 241000206607 Porphyra umbilicalis Species 0.000 description 12
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
• 238000003556 assay Methods 0.000 description 12
• 239000012267 brine Substances 0.000 description 12
• 235000019439 ethyl acetate Nutrition 0.000 description 12
• 238000010992 reflux Methods 0.000 description 12
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
• RAPGMEHFXAWYSY-UHFFFAOYSA-N 6-isothiocyanato-1h-benzimidazole Chemical compound S=C=NC1=CC=C2N=CNC2=C1 RAPGMEHFXAWYSY-UHFFFAOYSA-N 0.000 description 11
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• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 9
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• MOZNZNKHRXRLLF-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)aniline Chemical compound C1CN(C)CCN1C1=CC=C(N)C=C1 MOZNZNKHRXRLLF-UHFFFAOYSA-N 0.000 description 8
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• 150000002540 isothiocyanates Chemical class 0.000 description 8
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• WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 7
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