JP2005522438A - ピリミジン化合物 - Google Patents

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Publication number

JP2005522438A

JP2005522438A JP2003565975A JP2003565975A JP2005522438A JP 2005522438 A JP2005522438 A JP 2005522438A JP 2003565975 A JP2003565975 A JP 2003565975A JP 2003565975 A JP2003565975 A JP 2003565975A JP 2005522438 A JP2005522438 A JP 2005522438A

Authority

JP

Japan

Prior art keywords

amino

phenyl

methyl

alkyl

pyrimidin

Prior art date

2002-02-08

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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• 150000003230 pyrimidines Chemical class 0.000 title abstract description 8
• 238000000034 method Methods 0.000 claims abstract description 61
• 102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 claims abstract description 39
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 38
• 101000753291 Homo sapiens Angiopoietin-1 receptor Proteins 0.000 claims abstract description 37
• 102100022014 Angiopoietin-1 receptor Human genes 0.000 claims abstract description 36
• 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 claims abstract description 34
• BJHCYTJNPVGSBZ-YXSASFKJSA-N 1-[4-[6-amino-5-[(Z)-methoxyiminomethyl]pyrimidin-4-yl]oxy-2-chlorophenyl]-3-ethylurea Chemical compound CCNC(=O)Nc1ccc(Oc2ncnc(N)c2\C=N/OC)cc1Cl BJHCYTJNPVGSBZ-YXSASFKJSA-N 0.000 claims abstract description 31
• 238000011282 treatment Methods 0.000 claims abstract description 20
• 150000001875 compounds Chemical class 0.000 claims description 140
• 229910052739 hydrogen Inorganic materials 0.000 claims description 126
• 239000001257 hydrogen Substances 0.000 claims description 121
• -1 C 1 -C 4 alkyl Chemical group 0.000 claims description 117
• 150000002431 hydrogen Chemical group 0.000 claims description 113
• 125000000217 alkyl group Chemical group 0.000 claims description 91
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 82
• 125000000623 heterocyclic group Chemical group 0.000 claims description 82
• 125000003118 aryl group Chemical group 0.000 claims description 74
• 150000003839 salts Chemical class 0.000 claims description 73
• 125000003545 alkoxy group Chemical group 0.000 claims description 71
• 125000001072 heteroaryl group Chemical group 0.000 claims description 60
• 239000012453 solvate Substances 0.000 claims description 56
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 55
• 125000004104 aryloxy group Chemical group 0.000 claims description 48
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 42
• 230000000694 effects Effects 0.000 claims description 38
• 229910052736 halogen Inorganic materials 0.000 claims description 35
• 150000002367 halogens Chemical group 0.000 claims description 35
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 31
• 208000035475 disorder Diseases 0.000 claims description 31
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 31
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
• 230000033115 angiogenesis Effects 0.000 claims description 29
• 239000003814 drug Substances 0.000 claims description 29
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 28
• 239000008194 pharmaceutical composition Substances 0.000 claims description 27
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 26
• 125000003282 alkyl amino group Chemical group 0.000 claims description 26
• 206010028980 Neoplasm Diseases 0.000 claims description 25
• 201000011510 cancer Diseases 0.000 claims description 24
• 230000006870 function Effects 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 24
• 241000124008 Mammalia Species 0.000 claims description 23
• 125000001769 aryl amino group Chemical group 0.000 claims description 23
• 229940079593 drug Drugs 0.000 claims description 22
• 239000000460 chlorine Substances 0.000 claims description 18
• 239000002246 antineoplastic agent Substances 0.000 claims description 17
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 15
• 102000009465 Growth Factor Receptors Human genes 0.000 claims description 15
• 108010009202 Growth Factor Receptors Proteins 0.000 claims description 15
• 229910052801 chlorine Inorganic materials 0.000 claims description 15
• 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 14
• 125000001188 haloalkyl group Chemical group 0.000 claims description 14
• 238000002360 preparation method Methods 0.000 claims description 14
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 13
• 108091008605 VEGF receptors Proteins 0.000 claims description 11
• 102000009484 Vascular Endothelial Growth Factor Receptors Human genes 0.000 claims description 11
• 229940034982 antineoplastic agent Drugs 0.000 claims description 10
• 125000001475 halogen functional group Chemical group 0.000 claims description 10
• 230000001404 mediated effect Effects 0.000 claims description 10
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 9
• 229910052757 nitrogen Inorganic materials 0.000 claims description 8
• 229940124530 sulfonamide Drugs 0.000 claims description 8
• 150000001408 amides Chemical class 0.000 claims description 7
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 6
• DTUXNRWKSVIUOF-UHFFFAOYSA-N 1-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-3-propylurea Chemical compound C1=CC(NC(=O)NCCC)=CC=C1N(C)C1=CC=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=N1 DTUXNRWKSVIUOF-UHFFFAOYSA-N 0.000 claims description 6
• 102000001301 EGF receptor Human genes 0.000 claims description 6
• 108060006698 EGF receptor Proteins 0.000 claims description 6
• 101000851007 Homo sapiens Vascular endothelial growth factor receptor 2 Proteins 0.000 claims description 6
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
• 239000003085 diluting agent Substances 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• 239000001301 oxygen Substances 0.000 claims description 5
• 229940124597 therapeutic agent Drugs 0.000 claims description 5
• 238000002560 therapeutic procedure Methods 0.000 claims description 5
• RJINUSFBYKYLTQ-UHFFFAOYSA-N 1-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-3-phenylthiourea Chemical compound C=1C=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=NC=1N(C)C(C=C1)=CC=C1NC(=S)NC1=CC=CC=C1 RJINUSFBYKYLTQ-UHFFFAOYSA-N 0.000 claims description 4
• 108091008606 PDGF receptors Proteins 0.000 claims description 4
• 102000011653 Platelet-Derived Growth Factor Receptors Human genes 0.000 claims description 4
• 229940091171 VEGFR-2 tyrosine kinase inhibitor Drugs 0.000 claims description 4
• 102100033178 Vascular endothelial growth factor receptor 1 Human genes 0.000 claims description 4
• 102100033179 Vascular endothelial growth factor receptor 3 Human genes 0.000 claims description 4
• 239000004202 carbamide Substances 0.000 claims description 4
• SQQWBSBBCSFQGC-JLHYYAGUSA-N ubiquinone-2 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CCC=C(C)C)=C(C)C1=O SQQWBSBBCSFQGC-JLHYYAGUSA-N 0.000 claims description 4
• LZWJEODSCLZMOY-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-5-yl)-3-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]urea Chemical compound C=1C=C(NC(=O)NC=2C=C3CCCC3=CC=2)C=CC=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 LZWJEODSCLZMOY-UHFFFAOYSA-N 0.000 claims description 3
• USCPNRWCYGQBGN-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-[4-[[2-(5-ethylsulfonyl-2-methoxyanilino)pyrimidin-4-yl]-methylamino]phenyl]urea Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2N=C(C=CN=2)N(C)C=2C=CC(NC(=O)NC=3C=C(Cl)C=CC=3)=CC=2)=C1 USCPNRWCYGQBGN-UHFFFAOYSA-N 0.000 claims description 3
• RZFLHAKBZISSBN-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-[4-[[2-[3-(methanesulfonamidomethyl)anilino]pyrimidin-4-yl]-methylamino]phenyl]urea Chemical compound C=1C=NC(NC=2C=C(CNS(C)(=O)=O)C=CC=2)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 RZFLHAKBZISSBN-UHFFFAOYSA-N 0.000 claims description 3
• ISIGZINVBPDMCU-UHFFFAOYSA-N 1-(3-fluorophenyl)-3-[4-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]urea;hydrochloride Chemical compound Cl.C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NC1=CC=CC(F)=C1 ISIGZINVBPDMCU-UHFFFAOYSA-N 0.000 claims description 3
• UIIXIQWTXSGBOP-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-[4-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]urea Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NC1=CC=C(F)C=C1 UIIXIQWTXSGBOP-UHFFFAOYSA-N 0.000 claims description 3
• RREMTKSPGOIRHQ-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]-3-[4-[methyl-[2-[3-(2-methylsulfonylethyl)anilino]pyrimidin-4-yl]amino]phenyl]urea Chemical compound C1=CC(NC(=O)NCCN(C)C)=CC=C1N(C)C1=CC=NC(NC=2C=C(CCS(C)(=O)=O)C=CC=2)=N1 RREMTKSPGOIRHQ-UHFFFAOYSA-N 0.000 claims description 3
• YBLPVRFSDNONDP-UHFFFAOYSA-N 1-[4-[[2-(5-ethylsulfonyl-2-methoxyanilino)pyrimidin-4-yl]-methylamino]phenyl]-3-(3-fluorophenyl)urea Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2N=C(C=CN=2)N(C)C=2C=CC(NC(=O)NC=3C=C(F)C=CC=3)=CC=2)=C1 YBLPVRFSDNONDP-UHFFFAOYSA-N 0.000 claims description 3
• RYIZQWVKFLSVHM-UHFFFAOYSA-N 1-[4-[[2-(5-ethylsulfonyl-2-methoxyanilino)pyrimidin-4-yl]-methylamino]phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2N=C(C=CN=2)N(C)C=2C=CC(NC(=O)NC=3C(=CC=C(C=3)C(F)(F)F)F)=CC=2)=C1 RYIZQWVKFLSVHM-UHFFFAOYSA-N 0.000 claims description 3
• DQXBQPHEQRETIN-UHFFFAOYSA-N 1-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-3-(2-phenylethyl)urea Chemical compound C=1C=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NCCC1=CC=CC=C1 DQXBQPHEQRETIN-UHFFFAOYSA-N 0.000 claims description 3
• ZMDSDIMLVJXMJA-UHFFFAOYSA-N 1-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-3-[4-(trifluoromethoxy)phenyl]urea Chemical compound C=1C=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NC1=CC=C(OC(F)(F)F)C=C1 ZMDSDIMLVJXMJA-UHFFFAOYSA-N 0.000 claims description 3
• NJVJUCVNZRPMBF-UHFFFAOYSA-N 1-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-3-phenylurea Chemical compound C=1C=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1 NJVJUCVNZRPMBF-UHFFFAOYSA-N 0.000 claims description 3
• GDFXLACGLHMCTE-UHFFFAOYSA-N 1-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-3-propan-2-ylurea Chemical compound C1=CC(NC(=O)NC(C)C)=CC=C1N(C)C1=CC=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=N1 GDFXLACGLHMCTE-UHFFFAOYSA-N 0.000 claims description 3
• LVGQTXJDZKXBOC-UHFFFAOYSA-N 1-[4-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-3-(4-phenylmethoxyphenyl)urea Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1OCC1=CC=CC=C1 LVGQTXJDZKXBOC-UHFFFAOYSA-N 0.000 claims description 3
• AHDFVTJYNGXCEO-UHFFFAOYSA-N 1-[4-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-3-[4-(4-methylpiperazine-1-carbonyl)phenyl]urea Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1C(=O)N1CCN(C)CC1 AHDFVTJYNGXCEO-UHFFFAOYSA-N 0.000 claims description 3
• WUUXQSKAAWHECK-UHFFFAOYSA-N 1-[4-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-3-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]urea Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1CN1CCN(C)CC1 WUUXQSKAAWHECK-UHFFFAOYSA-N 0.000 claims description 3
• CCGBGVNOJXOFAR-UHFFFAOYSA-N 1-butyl-3-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]urea Chemical compound C1=CC(NC(=O)NCCCC)=CC=C1N(C)C1=CC=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=N1 CCGBGVNOJXOFAR-UHFFFAOYSA-N 0.000 claims description 3
• HQILAAKXJCORFA-UHFFFAOYSA-N 1-cyclohexyl-3-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]urea Chemical compound C=1C=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NC1CCCCC1 HQILAAKXJCORFA-UHFFFAOYSA-N 0.000 claims description 3
• QCXCNKJISLRDOZ-UHFFFAOYSA-N 1-ethyl-3-[4-[methyl-[2-[4-[2-(methylsulfamoyl)ethyl]anilino]pyrimidin-4-yl]amino]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1N(C)C1=CC=NC(NC=2C=CC(CCS(=O)(=O)NC)=CC=2)=N1 QCXCNKJISLRDOZ-UHFFFAOYSA-N 0.000 claims description 3
• RZBKPAOZLPAYEX-UHFFFAOYSA-N 1-methyl-1-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-3-phenylurea Chemical compound C=1C=C(N(C)C=2N=C(NC=3C=C(CS(C)(=O)=O)C=CC=3)N=CC=2)C=CC=1N(C)C(=O)NC1=CC=CC=C1 RZBKPAOZLPAYEX-UHFFFAOYSA-N 0.000 claims description 3
• VRVGEKJEMKGQCS-UHFFFAOYSA-N 1-tert-butyl-3-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]urea Chemical compound C=1C=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=NC=1N(C)C1=CC=C(NC(=O)NC(C)(C)C)C=C1 VRVGEKJEMKGQCS-UHFFFAOYSA-N 0.000 claims description 3
• WTTQMMJLQSHYGL-UHFFFAOYSA-N 2-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-1-phenylguanidine Chemical compound C=1C=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=NC=1N(C)C(C=C1)=CC=C1N=C(N)NC1=CC=CC=C1 WTTQMMJLQSHYGL-UHFFFAOYSA-N 0.000 claims description 3
• 101000851018 Homo sapiens Vascular endothelial growth factor receptor 1 Proteins 0.000 claims description 3
• 101000851030 Homo sapiens Vascular endothelial growth factor receptor 3 Proteins 0.000 claims description 3
• 108010090091 TIE-2 Receptor Proteins 0.000 claims description 3
• 102000012753 TIE-2 Receptor Human genes 0.000 claims description 3
• VYWQTJWGWLKBQA-UHFFFAOYSA-N [amino(hydroxy)methylidene]azanium;chloride Chemical compound Cl.NC(N)=O VYWQTJWGWLKBQA-UHFFFAOYSA-N 0.000 claims description 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
• ROIHUUVUCIGOLZ-UHFFFAOYSA-N n-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-1-phenylmethanesulfonamide Chemical compound C=1C=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=NC=1N(C)C(C=C1)=CC=C1NS(=O)(=O)CC1=CC=CC=C1 ROIHUUVUCIGOLZ-UHFFFAOYSA-N 0.000 claims description 3
• XGJGNIZVSIGIJT-UHFFFAOYSA-N n-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-2-phenylacetamide Chemical compound C=1C=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=NC=1N(C)C(C=C1)=CC=C1NC(=O)CC1=CC=CC=C1 XGJGNIZVSIGIJT-UHFFFAOYSA-N 0.000 claims description 3
• BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 claims description 3
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 3
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
• XIDCNIZERXGXGB-UHFFFAOYSA-N CN(C1=CC=C(C=C1)NC(=O)NC2=C(C=CC(=C2)C(F)(F)F)F)C3=NC(=NC=C3)NC4=CC=CC=C4 Chemical compound CN(C1=CC=C(C=C1)NC(=O)NC2=C(C=CC(=C2)C(F)(F)F)F)C3=NC(=NC=C3)NC4=CC=CC=C4 XIDCNIZERXGXGB-UHFFFAOYSA-N 0.000 claims description 2
• MXUBDZBAYUHPDY-UHFFFAOYSA-N CN(C1=NC(=NC=C1)NC2=CC=CC=C2)C3=CC=CC(=C3)NC(=O)NC4=C(C=CC(=C4)C(F)(F)F)F Chemical compound CN(C1=NC(=NC=C1)NC2=CC=CC=C2)C3=CC=CC(=C3)NC(=O)NC4=C(C=CC(=C4)C(F)(F)F)F MXUBDZBAYUHPDY-UHFFFAOYSA-N 0.000 claims description 2
• 102000044591 ErbB-4 Receptor Human genes 0.000 claims 1
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• 239000004480 active ingredient Substances 0.000 description 10
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• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 7
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• 235000019439 ethyl acetate Nutrition 0.000 description 7
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