DK2970211T3 - HISTONDEMETHYLASE INHIBITORS - Google Patents

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Publication number

DK2970211T3

DK2970211T3 DK14768099.5T DK14768099T DK2970211T3 DK 2970211 T3 DK2970211 T3 DK 2970211T3 DK 14768099 T DK14768099 T DK 14768099T DK 2970211 T3 DK2970211 T3 DK 2970211T3

Authority

DK

Denmark

Prior art keywords

pyrimidin

alkyl

found

calc

pyrido

Prior art date

2013-03-15

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• 239000003112 inhibitor Substances 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims description 383
• 238000000034 method Methods 0.000 claims description 201
• -1 prrazinyl Chemical group 0.000 claims description 136
• 125000000217 alkyl group Chemical group 0.000 claims description 96
• 239000000203 mixture Substances 0.000 claims description 77
• 125000000623 heterocyclic group Chemical group 0.000 claims description 64
• 125000001072 heteroaryl group Chemical group 0.000 claims description 58
• 125000003118 aryl group Chemical group 0.000 claims description 46
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 45
• 150000003839 salts Chemical class 0.000 claims description 38
• 229910052739 hydrogen Inorganic materials 0.000 claims description 32
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 28
• 125000005884 carbocyclylalkyl group Chemical group 0.000 claims description 25
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
• 108010074870 Histone Demethylases Proteins 0.000 claims description 20
• 102000008157 Histone Demethylases Human genes 0.000 claims description 20
• 239000001257 hydrogen Substances 0.000 claims description 18
• 206010028980 Neoplasm Diseases 0.000 claims description 17
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 16
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 15
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
• 125000003545 alkoxy group Chemical group 0.000 claims description 10
• 125000003282 alkyl amino group Chemical group 0.000 claims description 10
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
• 201000011510 cancer Diseases 0.000 claims description 9
• 239000001301 oxygen Substances 0.000 claims description 9
• 229910052760 oxygen Inorganic materials 0.000 claims description 9
• 230000002401 inhibitory effect Effects 0.000 claims description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims description 8
• 238000011282 treatment Methods 0.000 claims description 8
• 125000001769 aryl amino group Chemical group 0.000 claims description 7
• 125000004104 aryloxy group Chemical group 0.000 claims description 7
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 6
• 238000000338 in vitro Methods 0.000 claims description 6
• 125000001153 fluoro group Chemical group F* 0.000 claims description 5
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
• 125000002541 furyl group Chemical group 0.000 claims description 3
• 229910052736 halogen Inorganic materials 0.000 claims description 3
• 150000002367 halogens Chemical class 0.000 claims description 3
• 125000002883 imidazolyl group Chemical group 0.000 claims description 3
• 125000001041 indolyl group Chemical group 0.000 claims description 3
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
• 125000005322 morpholin-1-yl group Chemical group 0.000 claims description 3
• 125000002757 morpholinyl group Chemical group 0.000 claims description 3
• 125000002971 oxazolyl group Chemical group 0.000 claims description 3
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 2
• 125000004487 4-tetrahydropyranyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
• 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims 2
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
• 229910006074 SO2NH2 Inorganic materials 0.000 claims 1
• 125000000732 arylene group Chemical group 0.000 claims 1
• 229910052731 fluorine Inorganic materials 0.000 claims 1
• 239000011737 fluorine Substances 0.000 claims 1
• 238000002360 preparation method Methods 0.000 description 232
• 238000005160 1H NMR spectroscopy Methods 0.000 description 221
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 180
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 101
• XIALRQNUNYOSJP-UHFFFAOYSA-N 2-chloro-1h-pyrido[3,4-d]pyrimidin-4-one Chemical compound N1=CC=C2C(O)=NC(Cl)=NC2=C1 XIALRQNUNYOSJP-UHFFFAOYSA-N 0.000 description 92
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 82
• 239000000243 solution Substances 0.000 description 64
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 63
• 125000002947 alkylene group Chemical group 0.000 description 60
• DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 58
• 239000011541 reaction mixture Substances 0.000 description 49
• 239000007787 solid Substances 0.000 description 36
• 125000004432 carbon atom Chemical group C* 0.000 description 32
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
• 238000006243 chemical reaction Methods 0.000 description 29
• 150000003254 radicals Chemical class 0.000 description 29
• HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 28
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
• 229910001868 water Inorganic materials 0.000 description 26
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
• 238000010898 silica gel chromatography Methods 0.000 description 24
• 108010033040 Histones Proteins 0.000 description 23
• 239000000126 substance Substances 0.000 description 22
• 210000004027 cell Anatomy 0.000 description 17
• 108090000623 proteins and genes Proteins 0.000 description 16
• 125000001424 substituent group Chemical group 0.000 description 16
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
• 101000615488 Homo sapiens Methyl-CpG-binding domain protein 2 Proteins 0.000 description 15
• 102100021299 Methyl-CpG-binding domain protein 2 Human genes 0.000 description 15
• 238000003556 assay Methods 0.000 description 15
• 239000000047 product Substances 0.000 description 15
• KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 14
• 101001088893 Homo sapiens Lysine-specific demethylase 4C Proteins 0.000 description 14
• 102100033230 Lysine-specific demethylase 4C Human genes 0.000 description 14
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
• 239000002904 solvent Substances 0.000 description 14
• QMOPAFMMLWUTKI-UHFFFAOYSA-N 1h-pyrido[3,4-d]pyrimidin-4-one Chemical group N1=CC=C2C(O)=NC=NC2=C1 QMOPAFMMLWUTKI-UHFFFAOYSA-N 0.000 description 13
• 102000006947 Histones Human genes 0.000 description 13
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
• 125000003709 fluoroalkyl group Chemical group 0.000 description 13
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
• 229910052799 carbon Inorganic materials 0.000 description 12
• 125000005843 halogen group Chemical group 0.000 description 12
• 235000018102 proteins Nutrition 0.000 description 12
• 102000004169 proteins and genes Human genes 0.000 description 12
• 102100033247 Lysine-specific demethylase 5B Human genes 0.000 description 11
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
• 239000002253 acid Substances 0.000 description 11
• 125000004450 alkenylene group Chemical group 0.000 description 11
• 229910052757 nitrogen Inorganic materials 0.000 description 11
• NNQSZQSLYJTIGS-SECBINFHSA-N 2-[1-[(3r)-pyrrolidin-3-yl]pyrazol-4-yl]oxy-1h-pyrido[3,4-d]pyrimidin-4-one Chemical compound N1C2=CN=CC=C2C(=O)N=C1OC(=C1)C=NN1[C@@H]1CCNC1 NNQSZQSLYJTIGS-SECBINFHSA-N 0.000 description 10
• NNQSZQSLYJTIGS-VIFPVBQESA-N 2-[1-[(3s)-pyrrolidin-3-yl]pyrazol-4-yl]oxy-1h-pyrido[3,4-d]pyrimidin-4-one Chemical compound N1C2=CN=CC=C2C(=O)N=C1OC(=C1)C=NN1[C@H]1CCNC1 NNQSZQSLYJTIGS-VIFPVBQESA-N 0.000 description 10
• 101001088883 Homo sapiens Lysine-specific demethylase 5B Proteins 0.000 description 10
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
• 125000004122 cyclic group Chemical group 0.000 description 10
• 238000001514 detection method Methods 0.000 description 10
• 201000010099 disease Diseases 0.000 description 10
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
• 239000000651 prodrug Substances 0.000 description 10
• 229940002612 prodrug Drugs 0.000 description 10
• MMQINJPURSSAHV-SNVBAGLBSA-N 2-[1-[(3r)-piperidin-3-yl]pyrazol-4-yl]oxy-1h-pyrido[3,4-d]pyrimidin-4-one Chemical compound N1C2=CN=CC=C2C(=O)N=C1OC(=C1)C=NN1[C@@H]1CCCNC1 MMQINJPURSSAHV-SNVBAGLBSA-N 0.000 description 9
• MMQINJPURSSAHV-JTQLQIEISA-N 2-[1-[(3s)-piperidin-3-yl]pyrazol-4-yl]oxy-1h-pyrido[3,4-d]pyrimidin-4-one Chemical compound N1C2=CN=CC=C2C(=O)N=C1OC(=C1)C=NN1[C@H]1CCCNC1 MMQINJPURSSAHV-JTQLQIEISA-N 0.000 description 9
• KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 9
• 125000003342 alkenyl group Chemical group 0.000 description 9
• 125000000304 alkynyl group Chemical group 0.000 description 9
• 235000018977 lysine Nutrition 0.000 description 9
• 238000007069 methylation reaction Methods 0.000 description 9
• 125000004433 nitrogen atom Chemical group N* 0.000 description 9
• 239000003921 oil Substances 0.000 description 9
• 239000011734 sodium Substances 0.000 description 9
• 229910000104 sodium hydride Inorganic materials 0.000 description 9
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 8
• 101100477411 Dictyostelium discoideum set1 gene Proteins 0.000 description 8
• 101000613625 Homo sapiens Lysine-specific demethylase 4A Proteins 0.000 description 8
• 101001088892 Homo sapiens Lysine-specific demethylase 5A Proteins 0.000 description 8
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 8
• 239000004472 Lysine Substances 0.000 description 8
• 102100040863 Lysine-specific demethylase 4A Human genes 0.000 description 8
• 102100033246 Lysine-specific demethylase 5A Human genes 0.000 description 8
• 230000011987 methylation Effects 0.000 description 8
• 238000003786 synthesis reaction Methods 0.000 description 8
• 238000002877 time resolved fluorescence resonance energy transfer Methods 0.000 description 8
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
• YFCIFWOJYYFDQP-PTWZRHHISA-N 4-[3-amino-6-[(1S,3S,4S)-3-fluoro-4-hydroxycyclohexyl]pyrazin-2-yl]-N-[(1S)-1-(3-bromo-5-fluorophenyl)-2-(methylamino)ethyl]-2-fluorobenzamide Chemical compound CNC[C@@H](NC(=O)c1ccc(cc1F)-c1nc(cnc1N)[C@H]1CC[C@H](O)[C@@H](F)C1)c1cc(F)cc(Br)c1 YFCIFWOJYYFDQP-PTWZRHHISA-N 0.000 description 7
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 7
• 230000008901 benefit Effects 0.000 description 7
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• 239000000758 substrate Substances 0.000 description 7
• 238000012360 testing method Methods 0.000 description 7
• BELUNASLYMZLPW-UHFFFAOYSA-N 1-benzylpyrazol-4-ol Chemical compound C1=C(O)C=NN1CC1=CC=CC=C1 BELUNASLYMZLPW-UHFFFAOYSA-N 0.000 description 6
• QXGNHCIXRGPFDC-JTQLQIEISA-N 2-[1-[(3s)-pyrrolidin-3-yl]pyrazol-4-yl]-1h-pyrido[3,4-d]pyrimidin-4-one Chemical compound N1C2=CN=CC=C2C(=O)N=C1C(=C1)C=NN1[C@H]1CCNC1 QXGNHCIXRGPFDC-JTQLQIEISA-N 0.000 description 6
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• 206010006187 Breast cancer Diseases 0.000 description 6
• 208000026310 Breast neoplasm Diseases 0.000 description 6
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• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
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• 229940009533 alpha-ketoglutaric acid Drugs 0.000 description 6
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• 239000000872 buffer Substances 0.000 description 6
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• 235000019439 ethyl acetate Nutrition 0.000 description 6
• 239000000543 intermediate Substances 0.000 description 6
• 239000012044 organic layer Substances 0.000 description 6
• 125000004430 oxygen atom Chemical group O* 0.000 description 6
• 125000003107 substituted aryl group Chemical group 0.000 description 6
• YZRNICKGRPOILY-UHFFFAOYSA-N 1-(1-phenylethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole Chemical compound C1=C(B2OC(C)(C)C(C)(C)O2)C=NN1C(C)C1=CC=CC=C1 YZRNICKGRPOILY-UHFFFAOYSA-N 0.000 description 5
• GCRITXZUWWISQM-UHFFFAOYSA-N 2-(1-piperidin-4-ylpyrazol-4-yl)oxy-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound N1CCC(CC1)N1N=CC(=C1)OC=1N=C(C2=C(N1)C=NC=C2)O GCRITXZUWWISQM-UHFFFAOYSA-N 0.000 description 5
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 5
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• 239000002585 base Substances 0.000 description 5
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• 239000003153 chemical reaction reagent Substances 0.000 description 5
• 125000004093 cyano group Chemical group *C#N 0.000 description 5
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• 125000005842 heteroatom Chemical group 0.000 description 5
• 150000002430 hydrocarbons Chemical group 0.000 description 5
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• 229910052742 iron Inorganic materials 0.000 description 5
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• OZLIBRFWDOSHRS-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-cyanoacetate Chemical compound N#CCC(=O)ON1C(=O)CCC1=O OZLIBRFWDOSHRS-UHFFFAOYSA-N 0.000 description 4
• KGNQDBQYEBMPFZ-UHFFFAOYSA-N 1-fluoro-4-iodobenzene Chemical compound FC1=CC=C(I)C=C1 KGNQDBQYEBMPFZ-UHFFFAOYSA-N 0.000 description 4
• XURKONIWFULYEQ-MRXNPFEDSA-N 2-[1-[(3r)-1-(4-fluorophenyl)piperidin-3-yl]pyrazol-4-yl]oxy-1h-pyrido[3,4-d]pyrimidin-4-one Chemical compound C1=CC(F)=CC=C1N1C[C@H](N2N=CC(OC=3NC4=CN=CC=C4C(=O)N=3)=C2)CCC1 XURKONIWFULYEQ-MRXNPFEDSA-N 0.000 description 4
• NZSIFZPWVWCNSG-LBPRGKRZSA-N 2-[1-[(3s)-1-cyclopropylsulfonylpiperidin-3-yl]pyrazol-4-yl]oxy-1h-pyrido[3,4-d]pyrimidin-4-one Chemical compound C([C@@H](C1)N2N=CC(=C2)OC2=NC(C3=CC=NC=C3N2)=O)CCN1S(=O)(=O)C1CC1 NZSIFZPWVWCNSG-LBPRGKRZSA-N 0.000 description 4
• WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 4
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• 206010005003 Bladder cancer Diseases 0.000 description 4
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• 244000201986 Cassia tora Species 0.000 description 4
• 108010077544 Chromatin Proteins 0.000 description 4
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• 206010058467 Lung neoplasm malignant Diseases 0.000 description 4
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
• 208000000236 Prostatic Neoplasms Diseases 0.000 description 4
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 4
• 150000007513 acids Chemical class 0.000 description 4
• 150000001412 amines Chemical class 0.000 description 4
• 125000004429 atom Chemical group 0.000 description 4
• PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 4
• 239000012267 brine Substances 0.000 description 4
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 4
• 229910000024 caesium carbonate Inorganic materials 0.000 description 4
• 230000001413 cellular effect Effects 0.000 description 4
• 210000003483 chromatin Anatomy 0.000 description 4
• 238000004587 chromatography analysis Methods 0.000 description 4
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 4
• 230000017858 demethylation Effects 0.000 description 4
• 238000010520 demethylation reaction Methods 0.000 description 4
• 230000004069 differentiation Effects 0.000 description 4
• 239000000284 extract Substances 0.000 description 4
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 description 4
• 125000000524 functional group Chemical group 0.000 description 4
• 201000005202 lung cancer Diseases 0.000 description 4
• 208000020816 lung neoplasm Diseases 0.000 description 4
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