SK3842002A3 - Quinazoline derivatives, process for the preparation thereof and pharmaceutical composition comprising the same - Google Patents

Info

Publication number

SK3842002A3

SK3842002A3 SK384-2002A SK3842002A SK3842002A3 SK 3842002 A3 SK3842002 A3 SK 3842002A3 SK 3842002 A SK3842002 A SK 3842002A SK 3842002 A3 SK3842002 A3 SK 3842002A3

Authority

SK

Slovakia

Prior art keywords

group

alkyl

carbon atoms

moiety

alkoxy

Prior art date

1999-09-21

Links

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• 238000000034 method Methods 0.000 title claims description 78
• 238000002360 preparation method Methods 0.000 title claims description 77
• 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
• 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 160
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 71
• 239000001257 hydrogen Substances 0.000 claims abstract description 71
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 43
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 38
• 108090000461 Aurora Kinase A Proteins 0.000 claims abstract description 36
• 102100032311 Aurora kinase A Human genes 0.000 claims abstract description 30
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 28
• 150000002148 esters Chemical class 0.000 claims abstract description 26
• 150000003839 salts Chemical class 0.000 claims abstract description 20
• 150000001408 amides Chemical class 0.000 claims abstract description 14
• 125000000217 alkyl group Chemical group 0.000 claims description 317
• 125000004432 carbon atom Chemical group C* 0.000 claims description 316
• 125000000623 heterocyclic group Chemical group 0.000 claims description 98
• 125000003545 alkoxy group Chemical group 0.000 claims description 97
• -1 cyano, amino Chemical group 0.000 claims description 85
• 229910052757 nitrogen Inorganic materials 0.000 claims description 74
• 125000000524 functional group Chemical group 0.000 claims description 64
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 62
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 57
• 125000001424 substituent group Chemical group 0.000 claims description 56
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 47
• 229910052736 halogen Inorganic materials 0.000 claims description 46
• 150000002367 halogens Chemical class 0.000 claims description 45
• 125000003118 aryl group Chemical group 0.000 claims description 44
• 229910052799 carbon Inorganic materials 0.000 claims description 44
• 150000002431 hydrogen Chemical class 0.000 claims description 43
• 125000004122 cyclic group Chemical group 0.000 claims description 41
• 125000005842 heteroatom Chemical group 0.000 claims description 40
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 36
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 35
• 150000002430 hydrocarbons Chemical class 0.000 claims description 32
• 239000001301 oxygen Substances 0.000 claims description 32
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 31
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 30
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 30
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 29
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 29
• 239000011593 sulfur Substances 0.000 claims description 29
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 27
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 27
• 125000004043 oxo group Chemical group O=* 0.000 claims description 25
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
• 125000005843 halogen group Chemical group 0.000 claims description 24
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 21
• 125000003342 alkenyl group Chemical group 0.000 claims description 19
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 16
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 16
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 16
• 229920006395 saturated elastomer Polymers 0.000 claims description 16
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 15
• 125000003282 alkyl amino group Chemical group 0.000 claims description 15
• 125000002947 alkylene group Chemical group 0.000 claims description 15
• 125000000304 alkynyl group Chemical group 0.000 claims description 15
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 13
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 12
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 12
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 12
• LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims description 11
• 239000000651 prodrug Substances 0.000 claims description 11
• 229940002612 prodrug Drugs 0.000 claims description 11
• 125000003418 alkyl amino alkoxy group Chemical group 0.000 claims description 10
• 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 10
• 125000003277 amino group Chemical group 0.000 claims description 10
• 125000002431 aminoalkoxy group Chemical group 0.000 claims description 10
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
• 229910052731 fluorine Inorganic materials 0.000 claims description 9
• 239000011737 fluorine Chemical group 0.000 claims description 9
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 8
• 125000006699 (C1-C3) hydroxyalkyl group Chemical group 0.000 claims description 8
• 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 8
• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 8
• 125000004429 atom Chemical group 0.000 claims description 8
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
• 229930195733 hydrocarbon Natural products 0.000 claims description 8
• 239000004215 Carbon black (E152) Substances 0.000 claims description 7
• 241001465754 Metazoa Species 0.000 claims description 7
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 7
• 125000004434 sulfur atom Chemical group 0.000 claims description 7
• 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims description 6
• 125000004423 acyloxy group Chemical group 0.000 claims description 6
• 150000001721 carbon Chemical group 0.000 claims description 6
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• 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 6
• 239000002243 precursor Substances 0.000 claims description 6
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
• 125000004450 alkenylene group Chemical group 0.000 claims description 5
• 125000004419 alkynylene group Chemical group 0.000 claims description 5
• 239000003814 drug Substances 0.000 claims description 5
• 230000002401 inhibitory effect Effects 0.000 claims description 5
• 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 4
• 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 4
• 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 4
• 125000004104 aryloxy group Chemical group 0.000 claims description 4
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
• 125000001589 carboacyl group Chemical group 0.000 claims description 4
• 229910052801 chlorine Inorganic materials 0.000 claims description 4
• 239000000460 chlorine Chemical group 0.000 claims description 4
• 125000001072 heteroaryl group Chemical group 0.000 claims description 4
• 125000002632 imidazolidinyl group Chemical group 0.000 claims description 4
• 125000004193 piperazinyl group Chemical group 0.000 claims description 4
• 125000003386 piperidinyl group Chemical group 0.000 claims description 4
• 125000006413 ring segment Chemical group 0.000 claims description 4
• 125000005415 substituted alkoxy group Chemical group 0.000 claims description 4
• 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 3
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 3
• 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 3
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
• 229910019142 PO4 Inorganic materials 0.000 claims description 3
• 229910052794 bromium Inorganic materials 0.000 claims description 3
• 125000005518 carboxamido group Chemical group 0.000 claims description 3
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 3
• 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 3
• 125000005646 oximino group Chemical group 0.000 claims description 3
• 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 3
• 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 2
• 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims description 2
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 2
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 2
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
• 125000004956 cyclohexylene group Chemical group 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 238000004519 manufacturing process Methods 0.000 claims description 2
• 125000000466 oxiranyl group Chemical group 0.000 claims description 2
• 125000003107 substituted aryl group Chemical group 0.000 claims description 2
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 2
• 125000001183 hydrocarbyl group Chemical group 0.000 claims 15
• 125000004414 alkyl thio group Chemical group 0.000 claims 3
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
• 239000010452 phosphate Substances 0.000 claims 1
• UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims 1
• 238000006467 substitution reaction Methods 0.000 claims 1
• 206010028980 Neoplasm Diseases 0.000 abstract description 16
• 201000011510 cancer Diseases 0.000 abstract description 9
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 2
• 239000003112 inhibitor Substances 0.000 abstract 1
• 125000000962 organic group Chemical group 0.000 abstract 1
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 224
• 239000007787 solid Substances 0.000 description 97
• 238000001819 mass spectrum Methods 0.000 description 93
• 238000005160 1H NMR spectroscopy Methods 0.000 description 71
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
• 239000000243 solution Substances 0.000 description 46
• 239000000203 mixture Substances 0.000 description 41
• 210000004027 cell Anatomy 0.000 description 39
• 239000011541 reaction mixture Substances 0.000 description 38
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 26
• 238000012360 testing method Methods 0.000 description 25
• 239000002904 solvent Substances 0.000 description 24
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 22
• 238000004128 high performance liquid chromatography Methods 0.000 description 18
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 18
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
• 239000004480 active ingredient Substances 0.000 description 15
• 239000002244 precipitate Substances 0.000 description 15
• 238000003828 vacuum filtration Methods 0.000 description 15
• UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 14
• 238000003556 assay Methods 0.000 description 13
• 108090000623 proteins and genes Proteins 0.000 description 13
• AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 12
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
• 238000001035 drying Methods 0.000 description 12
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
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• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 11
• 230000000694 effects Effects 0.000 description 11
• 239000000725 suspension Substances 0.000 description 11
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• 230000022131 cell cycle Effects 0.000 description 10
• 239000012044 organic layer Substances 0.000 description 10
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• 239000012298 atmosphere Substances 0.000 description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
• 238000001727 in vivo Methods 0.000 description 9
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
• 108091003079 Bovine Serum Albumin Proteins 0.000 description 8
• 108020004414 DNA Proteins 0.000 description 8
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
• 238000006243 chemical reaction Methods 0.000 description 8
• 239000002609 medium Substances 0.000 description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
• 239000000843 powder Substances 0.000 description 8
• 238000010992 reflux Methods 0.000 description 8
• 239000007858 starting material Substances 0.000 description 8
• 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 7
• 102000004190 Enzymes Human genes 0.000 description 7
• 108090000790 Enzymes Proteins 0.000 description 7
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
• ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 7
• 229930182816 L-glutamine Natural products 0.000 description 7
• 229930182555 Penicillin Natural products 0.000 description 7
• JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 7
• 238000009835 boiling Methods 0.000 description 7
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• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
• 229940049954 penicillin Drugs 0.000 description 7
• 102000004169 proteins and genes Human genes 0.000 description 7
• 229960005322 streptomycin Drugs 0.000 description 7
• CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 6
• WOVKYSAHUYNSMH-RRKCRQDMSA-N 5-bromodeoxyuridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(Br)=C1 WOVKYSAHUYNSMH-RRKCRQDMSA-N 0.000 description 6
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
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• BELBBZDIHDAJOR-UHFFFAOYSA-N Phenolsulfonephthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2S(=O)(=O)O1 BELBBZDIHDAJOR-UHFFFAOYSA-N 0.000 description 6
• 108091000080 Phosphotransferase Proteins 0.000 description 6
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• LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 6
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 6
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• 102000020233 phosphotransferase Human genes 0.000 description 6
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• 230000002062 proliferating effect Effects 0.000 description 6
• 239000003765 sweetening agent Substances 0.000 description 6
• COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 6
• DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 6
• 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 5
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 5
• LLLHRNQLGUOJHP-UHFFFAOYSA-N 4-chloro-6,7-dimethoxyquinazoline Chemical compound C1=NC(Cl)=C2C=C(OC)C(OC)=CC2=N1 LLLHRNQLGUOJHP-UHFFFAOYSA-N 0.000 description 5
• 239000005909 Kieselgur Substances 0.000 description 5
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• 230000005764 inhibitory process Effects 0.000 description 5
• 239000006166 lysate Substances 0.000 description 5
• RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 5
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