MX2008015765A - Inhibidores de aldh-2 en el tratamiento de adiccion. - Google Patents

Info

Publication number

MX2008015765A

MX2008015765A MX2008015765A MX2008015765A MX2008015765A MX 2008015765 A MX2008015765 A MX 2008015765A MX 2008015765 A MX2008015765 A MX 2008015765A MX 2008015765 A MX2008015765 A MX 2008015765A MX 2008015765 A MX2008015765 A MX 2008015765A

Authority

MX

Mexico

Prior art keywords

phenyl

chromen

hydroxy

methyl

methoxy

Prior art date

2006-07-27

Links

• Espacenet
• Global Dossier
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• 238000011282 treatment Methods 0.000 title claims description 32
• 206010012335 Dependence Diseases 0.000 title abstract description 15
• 239000003112 inhibitor Substances 0.000 title abstract description 12
• -1 amphetamines Chemical compound 0.000 claims abstract description 315
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 69
• ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims abstract description 66
• 229960003920 cocaine Drugs 0.000 claims abstract description 33
• SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims abstract description 20
• 239000003795 chemical substances by application Substances 0.000 claims abstract description 20
• VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims abstract description 20
• 229960002715 nicotine Drugs 0.000 claims abstract description 20
• SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims abstract description 20
• 229960003638 dopamine Drugs 0.000 claims abstract description 10
• 241000124008 Mammalia Species 0.000 claims abstract description 7
• 150000001875 compounds Chemical class 0.000 claims description 288
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 177
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 134
• 125000000217 alkyl group Chemical group 0.000 claims description 85
• 125000001072 heteroaryl group Chemical group 0.000 claims description 69
• 229910052739 hydrogen Inorganic materials 0.000 claims description 59
• 239000001257 hydrogen Substances 0.000 claims description 58
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 56
• 125000003118 aryl group Chemical group 0.000 claims description 52
• 125000001424 substituent group Chemical group 0.000 claims description 51
• 229910052736 halogen Inorganic materials 0.000 claims description 48
• 150000002367 halogens Chemical group 0.000 claims description 48
• 238000000034 method Methods 0.000 claims description 40
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 38
• 125000003545 alkoxy group Chemical group 0.000 claims description 37
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 37
• 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 claims description 34
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 34
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 33
• 229910052760 oxygen Inorganic materials 0.000 claims description 33
• 239000001301 oxygen Substances 0.000 claims description 33
• 125000004432 carbon atom Chemical group C* 0.000 claims description 31
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 30
• 125000000623 heterocyclic group Chemical group 0.000 claims description 30
• 239000002253 acid Substances 0.000 claims description 29
• 125000002947 alkylene group Chemical group 0.000 claims description 25
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
• 239000005711 Benzoic acid Substances 0.000 claims description 22
• 125000003342 alkenyl group Chemical group 0.000 claims description 22
• 125000000304 alkynyl group Chemical group 0.000 claims description 20
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
• 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 claims description 16
• QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 14
• MFVRXOUUMYWYLQ-UHFFFAOYSA-N N-[4-(4-oxochromen-2-yl)phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=C(C=C1)C=1OC2=CC=CC=C2C(C=1)=O MFVRXOUUMYWYLQ-UHFFFAOYSA-N 0.000 claims description 14
• 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 claims description 13
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 13
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 11
• WGSXKYXKAARAKD-UHFFFAOYSA-N 1-fluoro-3-isocyanato-5-(trifluoromethyl)benzene Chemical group FC1=CC(N=C=O)=CC(C(F)(F)F)=C1 WGSXKYXKAARAKD-UHFFFAOYSA-N 0.000 claims description 10
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 10
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
• 229910019142 PO4 Inorganic materials 0.000 claims description 9
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 9
• 239000010452 phosphate Substances 0.000 claims description 9
• YYOOFJZTRCPVFD-UHFFFAOYSA-N 3-[[3-[4-(methanesulfonamido)phenyl]-4-oxochromen-7-yl]oxymethyl]benzoic acid Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C(O)=O)=CC=C2C1=O YYOOFJZTRCPVFD-UHFFFAOYSA-N 0.000 claims description 8
• 229940095102 methyl benzoate Drugs 0.000 claims description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims description 8
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 8
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 7
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
• 101100516554 Caenorhabditis elegans nhr-5 gene Proteins 0.000 claims description 7
• QYQCFHLVHVSJTA-UHFFFAOYSA-N 2-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]benzonitrile Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3C(=CC=CC=3)C#N)=CC=C2C1=O QYQCFHLVHVSJTA-UHFFFAOYSA-N 0.000 claims description 6
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 6
• VTVSNUPYDKMEIP-UHFFFAOYSA-N O=C(COC(OC1=CC=CC=C11)=CC1=O)C1=C(C(F)(F)F)C=CC=C1 Chemical compound O=C(COC(OC1=CC=CC=C11)=CC1=O)C1=C(C(F)(F)F)C=CC=C1 VTVSNUPYDKMEIP-UHFFFAOYSA-N 0.000 claims description 6
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
• MTZQAGJQAFMTAQ-UHFFFAOYSA-N benzoic acid ethyl ester Natural products CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims description 6
• XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Chemical group N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 6
• UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 6
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
• 239000000126 substance Substances 0.000 claims description 6
• 229910052717 sulfur Inorganic materials 0.000 claims description 6
• 239000011593 sulfur Chemical group 0.000 claims description 6
• FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims description 5
• GFHOVQHRHREPPZ-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-(3-phenylpropoxy)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCCC=3C=CC=CC=3)=CC=C2C1=O GFHOVQHRHREPPZ-UHFFFAOYSA-N 0.000 claims description 5
• GUZLXSMJFYJQFJ-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-(5-pyridin-4-yl-1,2,4-oxadiazol-3-yl)ethoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCC=3N=C(ON=3)C=3C=CN=CC=3)=CC=C2C1=O GUZLXSMJFYJQFJ-UHFFFAOYSA-N 0.000 claims description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 4
• FXSYGQPEYZJTHI-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-(5-pyridin-3-yl-1,3,4-oxadiazol-2-yl)ethoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCC=3OC(=NN=3)C=3C=NC=CC=3)=CC=C2C1=O FXSYGQPEYZJTHI-UHFFFAOYSA-N 0.000 claims description 4
• NXRZHVXCUDNZGL-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[6-(1h-pyrazol-5-yl)pyridin-3-yl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3C=NC(=CC=3)C3=NNC=C3)=CC=C2C1=O NXRZHVXCUDNZGL-UHFFFAOYSA-N 0.000 claims description 4
• HSTCXSZUDZOKRP-UHFFFAOYSA-N 7-[2-(3-fluorophenyl)-2-oxoethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC(=O)C=3C=C(F)C=CC=3)=CC=C2C1=O HSTCXSZUDZOKRP-UHFFFAOYSA-N 0.000 claims description 4
• FAHBJKISWFYSTG-UHFFFAOYSA-N 7-[[5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=CC(F)=CC=3)=CC=C2C1=O FAHBJKISWFYSTG-UHFFFAOYSA-N 0.000 claims description 4
• KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical group N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 4
• UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 4
• 101100240527 Caenorhabditis elegans nhr-22 gene Proteins 0.000 claims description 4
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 4
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 4
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical group C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 4
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical group N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
• DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 150000002148 esters Chemical class 0.000 claims description 4
• MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 4
• AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical group C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
• 229940127240 opiate Drugs 0.000 claims description 4
• RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 claims description 4
• 125000004193 piperazinyl group Chemical group 0.000 claims description 4
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 3
• BISVYANBIFBJIA-UHFFFAOYSA-N 2-[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy-n-[3-(trifluoromethyl)phenyl]acetamide Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC(=O)NC=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O BISVYANBIFBJIA-UHFFFAOYSA-N 0.000 claims description 3
• WINCSZBUBUGNCB-UHFFFAOYSA-N 2-[[3-(trifluoromethyl)phenyl]methoxy]chromen-4-one Chemical compound FC(C=1C=C(C=CC=1)COC=1OC2=C(C(C=1)=O)C=CC=C2)(F)F WINCSZBUBUGNCB-UHFFFAOYSA-N 0.000 claims description 3
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 3
• ZJWNWERIHPKYCW-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-(2-phenylethoxy)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCC=3C=CC=CC=3)=CC=C2C1=O ZJWNWERIHPKYCW-UHFFFAOYSA-N 0.000 claims description 3
• CTTKSJXFCLZWEY-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-(2-piperazin-1-ylethoxy)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCN3CCNCC3)=CC=C2C1=O CTTKSJXFCLZWEY-UHFFFAOYSA-N 0.000 claims description 3
• GABUIDRLSZLRFS-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-(pyridin-2-ylmethoxy)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=CC=CC=3)=CC=C2C1=O GABUIDRLSZLRFS-UHFFFAOYSA-N 0.000 claims description 3
• LYOPHGBGGFBIAP-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-(pyridin-4-ylmethoxy)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3C=CN=CC=3)=CC=C2C1=O LYOPHGBGGFBIAP-UHFFFAOYSA-N 0.000 claims description 3
• SGWYZMJMBDTNPE-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[(3-phenyl-1,2,4-oxadiazol-5-yl)methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3ON=C(N=3)C=3C=CC=CC=3)=CC=C2C1=O SGWYZMJMBDTNPE-UHFFFAOYSA-N 0.000 claims description 3
• GQHHGMIEWPYQLZ-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[(3-pyridin-3-yl-1,2,4-oxadiazol-5-yl)methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3ON=C(N=3)C=3C=NC=CC=3)=CC=C2C1=O GQHHGMIEWPYQLZ-UHFFFAOYSA-N 0.000 claims description 3
• FFXQJURUOMILQH-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[(5-phenyl-1,2,4-oxadiazol-3-yl)methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=CC=CC=3)=CC=C2C1=O FFXQJURUOMILQH-UHFFFAOYSA-N 0.000 claims description 3
• NPDZVHPRRHSDIJ-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[(5-pyridin-2-yl-1,2,4-oxadiazol-3-yl)methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3N=CC=CC=3)=CC=C2C1=O NPDZVHPRRHSDIJ-UHFFFAOYSA-N 0.000 claims description 3
• HKEWKJSYDITCPM-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-(5-pyridin-2-yl-1,2,4-oxadiazol-3-yl)ethoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCC=3N=C(ON=3)C=3N=CC=CC=3)=CC=C2C1=O HKEWKJSYDITCPM-UHFFFAOYSA-N 0.000 claims description 3
• AFPFBJUMGHWWSF-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-(5-pyridin-3-yl-1,2,4-oxadiazol-3-yl)ethoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCC=3N=C(ON=3)C=3C=NC=CC=3)=CC=C2C1=O AFPFBJUMGHWWSF-UHFFFAOYSA-N 0.000 claims description 3
• XZZGBJWFXVPVMV-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[3-(2h-tetrazol-5-yl)phenyl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C=3NN=NN=3)=CC=C2C1=O XZZGBJWFXVPVMV-UHFFFAOYSA-N 0.000 claims description 3
• ORRIPWVLGBZIDZ-UHFFFAOYSA-N 7-[2-(4-chlorophenoxy)ethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCOC=3C=CC(Cl)=CC=3)=CC=C2C1=O ORRIPWVLGBZIDZ-UHFFFAOYSA-N 0.000 claims description 3
• FAAGZNJVSVYNSW-UHFFFAOYSA-N 7-[2-(4-fluorophenyl)-2-oxoethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC(=O)C=3C=CC(F)=CC=3)=CC=C2C1=O FAAGZNJVSVYNSW-UHFFFAOYSA-N 0.000 claims description 3
• JAGZCQBDQUBNEH-UHFFFAOYSA-N 7-[2-[4-(3-chlorophenyl)piperazin-1-yl]ethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCN3CCN(CC3)C=3C=C(Cl)C=CC=3)=CC=C2C1=O JAGZCQBDQUBNEH-UHFFFAOYSA-N 0.000 claims description 3
• COLMHOKXSWZSER-UHFFFAOYSA-N 7-[[2-(3,5-difluorophenyl)-1,3-oxazol-4-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(OC=3)C=3C=C(F)C=C(F)C=3)=CC=C2C1=O COLMHOKXSWZSER-UHFFFAOYSA-N 0.000 claims description 3
• GZQHEBGZIKUMDM-UHFFFAOYSA-N 7-[[5-(3-fluorophenyl)-1,2,4-oxadiazol-3-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(F)C=CC=3)=CC=C2C1=O GZQHEBGZIKUMDM-UHFFFAOYSA-N 0.000 claims description 3
• MYGSHFQAKIJDHL-UHFFFAOYSA-N COC1=C(C=CC=C1)C1=NC(=NO1)COC=1OC2=CC=CC=C2C(C=1)=O Chemical compound COC1=C(C=CC=C1)C1=NC(=NO1)COC=1OC2=CC=CC=C2C(C=1)=O MYGSHFQAKIJDHL-UHFFFAOYSA-N 0.000 claims description 3
• FAWSYNZXTZVRCG-UHFFFAOYSA-N O=C1C2=CC=CC=C2OC(OCC2=COC(C(C=C3F)=CC(F)=C3F)=N2)=C1 Chemical compound O=C1C2=CC=CC=C2OC(OCC2=COC(C(C=C3F)=CC(F)=C3F)=N2)=C1 FAWSYNZXTZVRCG-UHFFFAOYSA-N 0.000 claims description 3
• IKHGWUPYCGAFGQ-UHFFFAOYSA-N O=C1C2=CC=CC=C2OC(OCC2=NOC(C3=CC(C4=NN=NN4)=CC=C3)=N2)=C1 Chemical compound O=C1C2=CC=CC=C2OC(OCC2=NOC(C3=CC(C4=NN=NN4)=CC=C3)=N2)=C1 IKHGWUPYCGAFGQ-UHFFFAOYSA-N 0.000 claims description 3
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
• ATHHXGZTWNVVOU-UHFFFAOYSA-N monomethyl-formamide Natural products CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims description 3
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
• DKYBVKMIZODYKL-UHFFFAOYSA-N 1,3-diazinane Chemical compound C1CNCNC1 DKYBVKMIZODYKL-UHFFFAOYSA-N 0.000 claims description 2
• WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 2
• TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 claims description 2
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