JP2009544742A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2009544742A5 JP2009544742A5 JP2009522029A JP2009522029A JP2009544742A5 JP 2009544742 A5 JP2009544742 A5 JP 2009544742A5 JP 2009522029 A JP2009522029 A JP 2009522029A JP 2009522029 A JP2009522029 A JP 2009522029A JP 2009544742 A5 JP2009544742 A5 JP 2009544742A5
- Authority
- JP
- Japan
- Prior art keywords
- chromen
- hydroxyphenyl
- phenyl
- methoxy
- trifluoromethyl
- Prior art date
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 claims description 77
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 58
- -1 CF 3 Chemical group 0.000 claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 46
- 125000001072 heteroaryl group Chemical group 0.000 claims description 37
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 34
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000001475 halogen functional group Chemical group 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 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
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- YEVVMGQTIHYLHJ-CYBMUJFWSA-N 7-[(1r)-1-[3-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl]ethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound O([C@H](C)C=1ON=C(N=1)C=1C=C(C=C(F)C=1)C(F)(F)F)C(C=1)=CC=C(C2=O)C=1OC=C2C1=CC=C(O)C=C1 YEVVMGQTIHYLHJ-CYBMUJFWSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products 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
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- XINYOLXTIGKVRM-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-oxo-2-[2-(trifluoromethyl)phenyl]ethoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC(=O)C=3C(=CC=CC=3)C(F)(F)F)=CC=C2C1=O XINYOLXTIGKVRM-UHFFFAOYSA-N 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- PMXLLFNDTDRGFI-UHFFFAOYSA-N n-[4-[7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-4-oxochromen-3-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O PMXLLFNDTDRGFI-UHFFFAOYSA-N 0.000 claims description 5
- 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 4
- SKVYHLULOMUGKX-UHFFFAOYSA-N 2-fluoro-5-[7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-4-oxochromen-3-yl]benzonitrile Chemical compound FC(F)(F)C1=CC(F)=CC(C=2ON=C(COC=3C=C4C(C(C(C=5C=C(C(F)=CC=5)C#N)=CO4)=O)=CC=3)N=2)=C1 SKVYHLULOMUGKX-UHFFFAOYSA-N 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- UIUCEBUXYPDPAJ-UHFFFAOYSA-N 3-(3-acetylphenyl)-7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one Chemical compound CC(=O)C1=CC=CC(C=2C(C3=CC=C(OCC=4N=C(ON=4)C=4C=C(C=C(F)C=4)C(F)(F)F)C=C3OC=2)=O)=C1 UIUCEBUXYPDPAJ-UHFFFAOYSA-N 0.000 claims description 4
- 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 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
- 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 4
- JGOMKMRNUIOXIC-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-[3-(trifluoromethyl)phenyl]-1,2-oxazol-3-yl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC3=NOC(=C3)C=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O JGOMKMRNUIOXIC-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
- RKGISUHWZBBCKR-UHFFFAOYSA-N 7-[2-[3-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl]ethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCC=3ON=C(N=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O RKGISUHWZBBCKR-UHFFFAOYSA-N 0.000 claims description 4
- FYMBTIMJLANAIU-UHFFFAOYSA-N 7-[[2-[3-fluoro-5-(trifluoromethyl)phenyl]-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(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O FYMBTIMJLANAIU-UHFFFAOYSA-N 0.000 claims description 4
- VQLYYLNXOIUOFU-UHFFFAOYSA-N 7-[[5-(4-chlorophenyl)-1,2-oxazol-3-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC3=NOC(=C3)C=3C=CC(Cl)=CC=3)=CC=C2C1=O VQLYYLNXOIUOFU-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 compound 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-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
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 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 description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 4
- FIFFBIMRAZGZIN-UHFFFAOYSA-N n-[4-[7-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methoxy]-4-oxochromen-3-yl]phenyl]methanesulfonamide Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1COC(C=1)=CC=C(C2=O)C=1OC=C2C1=CC=C(NS(C)(=O)=O)C=C1 FIFFBIMRAZGZIN-UHFFFAOYSA-N 0.000 claims description 4
- QXYPVJQYTBVSBE-UHFFFAOYSA-N n-[4-[7-[[5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl]methoxy]-4-oxochromen-3-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=CC(F)=CC=3)=CC=C2C1=O QXYPVJQYTBVSBE-UHFFFAOYSA-N 0.000 claims description 4
- NJYMIOGEDYKFQY-UHFFFAOYSA-N n-[4-[7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-4-oxochromen-3-yl]phenyl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=C(C=2C(C3=CC=C(OCC=4N=C(ON=4)C=4C=C(C=C(F)C=4)C(F)(F)F)C=C3OC=2)=O)C=C1 NJYMIOGEDYKFQY-UHFFFAOYSA-N 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- YARRGUWVCVLKCS-UHFFFAOYSA-N 2-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]-1,3-oxazole-4-carboxylic acid Chemical compound OC(=O)C1=COC(COC=2C=C3C(C(C(C=4C=CC(O)=CC=4)=CO3)=O)=CC=2)=N1 YARRGUWVCVLKCS-UHFFFAOYSA-N 0.000 claims description 3
- QZQVAPKTAUQPCF-UHFFFAOYSA-N 2-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]-N-methyl-1,3-oxazole-4-carboxamide Chemical compound CNC(=O)C1=COC(COC=2C=C3C(C(C(C=4C=CC(O)=CC=4)=CO3)=O)=CC=2)=N1 QZQVAPKTAUQPCF-UHFFFAOYSA-N 0.000 claims description 3
- OESBYEICGXYNBT-UHFFFAOYSA-N 3-(4-aminophenyl)-7-[[5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one Chemical compound C1=CC(N)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O OESBYEICGXYNBT-UHFFFAOYSA-N 0.000 claims description 3
- MLHOACBDJNPKJC-UHFFFAOYSA-N 3-(4-aminophenyl)-7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one Chemical compound C1=CC(N)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O MLHOACBDJNPKJC-UHFFFAOYSA-N 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
- 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
- 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
- AHYUTGIZIZIDKP-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[(5-pyridin-2-yl-1,2-oxazol-3-yl)methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC3=NOC(=C3)C=3N=CC=CC=3)=CC=C2C1=O AHYUTGIZIZIDKP-UHFFFAOYSA-N 0.000 claims description 3
- BLMUWBUJDTZGQV-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[(5-pyridin-3-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=3C=NC=CC=3)=CC=C2C1=O BLMUWBUJDTZGQV-UHFFFAOYSA-N 0.000 claims description 3
- XDBUTBAUTWQRHY-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[(5-pyridin-3-yl-1,3,4-oxadiazol-2-yl)methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3OC(=NN=3)C=3C=NC=CC=3)=CC=C2C1=O XDBUTBAUTWQRHY-UHFFFAOYSA-N 0.000 claims description 3
- HKXIGXKVBVSHLZ-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-[3-(trifluoromethyl)phenyl]ethoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCC=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O HKXIGXKVBVSHLZ-UHFFFAOYSA-N 0.000 claims description 3
- PMIDRXUFPZSRBZ-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-[4-(4-methoxyphenyl)piperazin-1-yl]ethoxy]chromen-4-one Chemical compound C1=CC(OC)=CC=C1N1CCN(CCOC=2C=C3C(C(C(C=4C=CC(O)=CC=4)=CO3)=O)=CC=2)CC1 PMIDRXUFPZSRBZ-UHFFFAOYSA-N 0.000 claims description 3
- YBRCUCDVZMFQDL-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]ethoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCN3CCN(CC3)C=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O YBRCUCDVZMFQDL-UHFFFAOYSA-N 0.000 claims description 3
- ZLHYZFVZAFHBEA-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-[[3-(trifluoromethyl)phenyl]methylamino]ethoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCNCC=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O ZLHYZFVZAFHBEA-UHFFFAOYSA-N 0.000 claims description 3
- BXQJHBUPOKYULL-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[2-(3,4,5-trifluorophenyl)-1,3-oxazol-4-yl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(OC=3)C=3C=C(F)C(F)=C(F)C=3)=CC=C2C1=O BXQJHBUPOKYULL-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
- MGBNIYZXARWXHW-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[3-[3-(trifluoromethyl)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=C(C=CC=3)C(F)(F)F)=CC=C2C1=O MGBNIYZXARWXHW-UHFFFAOYSA-N 0.000 claims description 3
- IJKBDDMBAHSXDV-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methoxy]chromen-4-one Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1COC(C=1)=CC=C(C2=O)C=1OC=C2C1=CC=C(O)C=C1 IJKBDDMBAHSXDV-UHFFFAOYSA-N 0.000 claims description 3
- IUQDULUMXAXWBP-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-[3-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-yl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3OC(=NN=3)C=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O IUQDULUMXAXWBP-UHFFFAOYSA-N 0.000 claims description 3
- GEOFIVBSXPVRPE-UHFFFAOYSA-N 3-[3-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]-1,2,4-oxadiazol-5-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2ON=C(COC=3C=C4C(C(C(C=5C=CC(O)=CC=5)=CO4)=O)=CC=3)N=2)=C1 GEOFIVBSXPVRPE-UHFFFAOYSA-N 0.000 claims description 3
- DSNYSUDIVYIEQH-UHFFFAOYSA-N 3-[7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-4-oxochromen-3-yl]benzonitrile Chemical compound FC(F)(F)C1=CC(F)=CC(C=2ON=C(COC=3C=C4C(C(C(C=5C=C(C=CC=5)C#N)=CO4)=O)=CC=3)N=2)=C1 DSNYSUDIVYIEQH-UHFFFAOYSA-N 0.000 claims description 3
- WVKZSEGADHUEKE-UHFFFAOYSA-N 3-[[3-(4-aminophenyl)-4-oxochromen-7-yl]oxymethyl]benzonitrile Chemical compound C1=CC(N)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C#N)=CC=C2C1=O WVKZSEGADHUEKE-UHFFFAOYSA-N 0.000 claims description 3
- XAYXXBMMIHLDQI-UHFFFAOYSA-N 3-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(COC=2C=C3C(C(C(C=4C=CC(O)=CC=4)=CO3)=O)=CC=2)=C1 XAYXXBMMIHLDQI-UHFFFAOYSA-N 0.000 claims description 3
- HEOQQDCLAMIWDE-UHFFFAOYSA-N 3-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]benzonitrile Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C#N)=CC=C2C1=O HEOQQDCLAMIWDE-UHFFFAOYSA-N 0.000 claims description 3
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 3
- IMLRTJCRZHHKRW-UHFFFAOYSA-N 4-[7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-4-oxochromen-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O IMLRTJCRZHHKRW-UHFFFAOYSA-N 0.000 claims description 3
- XJKPZYKFZKQYCH-UHFFFAOYSA-N 4-[7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-4-oxochromen-3-yl]benzonitrile Chemical compound FC(F)(F)C1=CC(F)=CC(C=2ON=C(COC=3C=C4C(C(C(C=5C=CC(=CC=5)C#N)=CO4)=O)=CC=3)N=2)=C1 XJKPZYKFZKQYCH-UHFFFAOYSA-N 0.000 claims description 3
- IYDPWNALDNSKDN-UHFFFAOYSA-N 4-methyl-n-[4-[7-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methoxy]-4-oxochromen-3-yl]phenyl]benzenesulfonamide Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1COC(C=1)=CC=C(C2=O)C=1OC=C2C(C=C1)=CC=C1NS(=O)(=O)C1=CC=C(C)C=C1 IYDPWNALDNSKDN-UHFFFAOYSA-N 0.000 claims description 3
- YEVVMGQTIHYLHJ-ZDUSSCGKSA-N 7-[(1s)-1-[3-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl]ethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound O([C@@H](C)C=1ON=C(N=1)C=1C=C(C=C(F)C=1)C(F)(F)F)C(C=1)=CC=C(C2=O)C=1OC=C2C1=CC=C(O)C=C1 YEVVMGQTIHYLHJ-ZDUSSCGKSA-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
- XFAQSZLKVGZYAA-UHFFFAOYSA-N 7-[2-(4-fluorophenyl)ethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCC=3C=CC(F)=CC=3)=CC=C2C1=O XFAQSZLKVGZYAA-UHFFFAOYSA-N 0.000 claims description 3
- KFKDUJLKVAOFQB-UHFFFAOYSA-N 7-[2-[2-(4-fluorophenyl)ethylamino]ethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCNCCC=3C=CC(F)=CC=3)=CC=C2C1=O KFKDUJLKVAOFQB-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
- KVDVZUSHUNMBDO-UHFFFAOYSA-N 7-[2-[4-(4-chlorophenyl)-1h-pyrazol-5-yl]ethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCC=3C(=CNN=3)C=3C=CC(Cl)=CC=3)=CC=C2C1=O KVDVZUSHUNMBDO-UHFFFAOYSA-N 0.000 claims description 3
- SXFJOYLSGKZQEM-UHFFFAOYSA-N 7-[2-[4-(4-fluorophenyl)piperazin-1-yl]ethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCN3CCN(CC3)C=3C=CC(F)=CC=3)=CC=C2C1=O SXFJOYLSGKZQEM-UHFFFAOYSA-N 0.000 claims description 3
- CVHDDJFLECTRJK-UHFFFAOYSA-N 7-[2-[5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl]ethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCC=3OC(=NN=3)C=3C=CC(F)=CC=3)=CC=C2C1=O CVHDDJFLECTRJK-UHFFFAOYSA-N 0.000 claims description 3
- KAJPBUYABCQBKK-UHFFFAOYSA-N 7-[2-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]ethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCC=3N=C(ON=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O KAJPBUYABCQBKK-UHFFFAOYSA-N 0.000 claims description 3
- MKMPNJBMKLCURY-UHFFFAOYSA-N 7-[3-[2-[3-fluoro-5-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]propoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCCC=3N=C(OC=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O MKMPNJBMKLCURY-UHFFFAOYSA-N 0.000 claims description 3
- PCKCUVRYWBKTEA-UHFFFAOYSA-N 7-[[2-(3,4-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(F)=CC=3)=CC=C2C1=O PCKCUVRYWBKTEA-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
- JKGRQKQIEYBYTJ-UHFFFAOYSA-N 7-[[2-(4-chlorophenyl)-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=CC(Cl)=CC=3)=CC=C2C1=O JKGRQKQIEYBYTJ-UHFFFAOYSA-N 0.000 claims description 3
- WEUVQMIOXQPDCT-UHFFFAOYSA-N 7-[[2-(4-fluorophenyl)-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=CC(F)=CC=3)=CC=C2C1=O WEUVQMIOXQPDCT-UHFFFAOYSA-N 0.000 claims description 3
- MOSZHACXXNIKAF-UHFFFAOYSA-N 7-[[5-(2-chlorophenyl)-1,3,4-oxadiazol-2-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3OC(=NN=3)C=3C(=CC=CC=3)Cl)=CC=C2C1=O MOSZHACXXNIKAF-UHFFFAOYSA-N 0.000 claims description 3
- YBAAQOVRDFBILI-UHFFFAOYSA-N 7-[[5-(3,4-dichlorophenyl)-1,2-oxazol-3-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC3=NOC(=C3)C=3C=C(Cl)C(Cl)=CC=3)=CC=C2C1=O YBAAQOVRDFBILI-UHFFFAOYSA-N 0.000 claims description 3
- BPVYYYUTPWPBES-UHFFFAOYSA-N 7-[[5-(3-fluorophenyl)-1,3,4-oxadiazol-2-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3OC(=NN=3)C=3C=C(F)C=CC=3)=CC=C2C1=O BPVYYYUTPWPBES-UHFFFAOYSA-N 0.000 claims description 3
- WMYIPPDFUUZWRA-UHFFFAOYSA-N 7-[[5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3OC(=NN=3)C=3C=CC(F)=CC=3)=CC=C2C1=O WMYIPPDFUUZWRA-UHFFFAOYSA-N 0.000 claims description 3
- CDZYCQRKIXMTJK-UHFFFAOYSA-N 7-[[5-[3,5-bis(trifluoromethyl)phenyl]-1,2-oxazol-3-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC3=NOC(=C3)C=3C=C(C=C(C=3)C(F)(F)F)C(F)(F)F)=CC=C2C1=O CDZYCQRKIXMTJK-UHFFFAOYSA-N 0.000 claims description 3
- YYGCAYSDPMCHAO-UHFFFAOYSA-N 7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-3-(4-methylsulfonylphenyl)chromen-4-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O YYGCAYSDPMCHAO-UHFFFAOYSA-N 0.000 claims description 3
- RKVAGAXJZJFEDQ-UHFFFAOYSA-N 7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-3-[4-(hydroxymethyl)phenyl]chromen-4-one Chemical compound C1=CC(CO)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O RKVAGAXJZJFEDQ-UHFFFAOYSA-N 0.000 claims description 3
- WBLWOFGQAXLTRU-UHFFFAOYSA-N 7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3OC(=NN=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O WBLWOFGQAXLTRU-UHFFFAOYSA-N 0.000 claims description 3
- OMUQGLOXIJKKRV-UHFFFAOYSA-N C1=CC(NS(=O)(=O)C)=CC=C1C1=C(O)OC2=CC(OCC=3C=C(C=CC=3)C(O)=O)=CC=C2C1=O Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=C(O)OC2=CC(OCC=3C=C(C=CC=3)C(O)=O)=CC=C2C1=O OMUQGLOXIJKKRV-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229960003638 dopamine Drugs 0.000 claims description 3
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 3
- IVLDGUKVQHCQCA-UHFFFAOYSA-N methyl 2-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]-1,3-oxazole-4-carboxylate Chemical compound COC(=O)C1=COC(COC=2C=C3C(C(C(C=4C=CC(O)=CC=4)=CO3)=O)=CC=2)=N1 IVLDGUKVQHCQCA-UHFFFAOYSA-N 0.000 claims description 3
- ZPUAMDNSBAFJTB-UHFFFAOYSA-N n-(2,4-difluorophenyl)-4-[2-[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyethyl]piperazine-1-carboxamide Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCN3CCN(CC3)C(=O)NC=3C(=CC(F)=CC=3)F)=CC=C2C1=O ZPUAMDNSBAFJTB-UHFFFAOYSA-N 0.000 claims description 3
- SZCZFEMWSJXEAC-UHFFFAOYSA-N n-(3-fluorophenyl)-4-[2-[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyethyl]piperazine-1-carboxamide Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCN3CCN(CC3)C(=O)NC=3C=C(F)C=CC=3)=CC=C2C1=O SZCZFEMWSJXEAC-UHFFFAOYSA-N 0.000 claims description 3
- FNYQPJGJSIQOQK-UHFFFAOYSA-N n-[4-[4-oxo-7-[(2-phenyl-1,3-oxazol-4-yl)methoxy]chromen-3-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3N=C(OC=3)C=3C=CC=CC=3)=CC=C2C1=O FNYQPJGJSIQOQK-UHFFFAOYSA-N 0.000 claims description 3
- IXNLDMMIZOOUOV-UHFFFAOYSA-N n-[4-[7-[(3-cyanophenyl)methoxy]-4-oxochromen-3-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C#N)=CC=C2C1=O IXNLDMMIZOOUOV-UHFFFAOYSA-N 0.000 claims description 3
- SCXVTUJUIPDVJB-UHFFFAOYSA-N n-[4-[7-[[5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl]methoxy]-4-oxochromen-3-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3OC(=NN=3)C=3C=CC(F)=CC=3)=CC=C2C1=O SCXVTUJUIPDVJB-UHFFFAOYSA-N 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 2
- 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
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 2
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 claims description 2
- 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 2
- NOIXNOMHHWGUTG-UHFFFAOYSA-N 2-[[4-[4-pyridin-4-yl-1-(2,2,2-trifluoroethyl)pyrazol-3-yl]phenoxy]methyl]quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(CC(F)(F)F)C=C1C1=CC=NC=C1 NOIXNOMHHWGUTG-UHFFFAOYSA-N 0.000 claims description 2
- VLRSADZEDXVUPG-UHFFFAOYSA-N 2-naphthalen-1-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=CC2=CC=CC=C12 VLRSADZEDXVUPG-UHFFFAOYSA-N 0.000 claims description 2
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims description 2
- CNFOIZLFPBENBM-UHFFFAOYSA-N 3-(3-fluorophenyl)-7-[[5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one Chemical compound FC1=CC=CC(C=2C(C3=CC=C(OCC=4N=C(ON=4)C=4C=C(C=CC=4)C(F)(F)F)C=C3OC=2)=O)=C1 CNFOIZLFPBENBM-UHFFFAOYSA-N 0.000 claims description 2
- XUJUWOOYHUYKRF-UHFFFAOYSA-N 3-(4-aminophenyl)-7-[[3-(trifluoromethoxy)phenyl]methoxy]chromen-4-one Chemical compound C1=CC(N)=CC=C1C1=COC2=CC(OCC=3C=C(OC(F)(F)F)C=CC=3)=CC=C2C1=O XUJUWOOYHUYKRF-UHFFFAOYSA-N 0.000 claims description 2
- QVCQIPUPLJTJKR-UHFFFAOYSA-N 3-(4-aminophenyl)-7-[[3-(trifluoromethyl)phenyl]methoxy]chromen-4-one Chemical compound C1=CC(N)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O QVCQIPUPLJTJKR-UHFFFAOYSA-N 0.000 claims description 2
- USHIWOJJGWWHKC-UHFFFAOYSA-N 3-(4-fluorophenyl)-7-[[5-(2-methoxyphenyl)-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one Chemical compound COC1=CC=CC=C1C1=NC(COC=2C=C3C(C(C(C=4C=CC(F)=CC=4)=CO3)=O)=CC=2)=NO1 USHIWOJJGWWHKC-UHFFFAOYSA-N 0.000 claims description 2
- RBCQQVFEINHKDD-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-2-(trifluoromethyl)-6-[[5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C(C(C1=C2)=O)=C(C(F)(F)F)OC1=CC=C2OCC1=NOC(C=2C=C(C=CC=2)C(F)(F)F)=N1 RBCQQVFEINHKDD-UHFFFAOYSA-N 0.000 claims description 2
- UNYJSYKAFBRDSF-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-6-[[3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C(C(C1=C2)=O)=COC1=CC=C2OCC1=NC(C=2C=C(C=CC=2)C(F)(F)F)=NO1 UNYJSYKAFBRDSF-UHFFFAOYSA-N 0.000 claims description 2
- IGLFEFCJHYKGNJ-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-6-[[5-[4-methoxy-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-2-(trifluoromethyl)chromen-4-one Chemical compound C1=C(C(F)(F)F)C(OC)=CC=C1C1=NC(COC=2C=C3C(=O)C(C=4C=CC(O)=CC=4)=C(OC3=CC=2)C(F)(F)F)=NO1 IGLFEFCJHYKGNJ-UHFFFAOYSA-N 0.000 claims description 2
- BTNOQJRRJASMJW-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-(pyridin-3-ylmethoxy)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3C=NC=CC=3)=CC=C2C1=O BTNOQJRRJASMJW-UHFFFAOYSA-N 0.000 claims description 2
- MYLUNEORTANDOK-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[(2-phenyl-1,3-oxazol-4-yl)methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(OC=3)C=3C=CC=CC=3)=CC=C2C1=O MYLUNEORTANDOK-UHFFFAOYSA-N 0.000 claims description 2
- YBSGKKITPLSUPH-FQEVSTJZSA-N 3-(4-hydroxyphenyl)-7-[(2s)-2-hydroxy-3-[[3-(trifluoromethyl)phenyl]methylamino]propoxy]chromen-4-one Chemical compound C([C@H](O)COC=1C=C2C(C(C(C=3C=CC(O)=CC=3)=CO2)=O)=CC=1)NCC1=CC=CC(C(F)(F)F)=C1 YBSGKKITPLSUPH-FQEVSTJZSA-N 0.000 claims description 2
- VIUAWBLQYVJXIW-IBGZPJMESA-N 3-(4-hydroxyphenyl)-7-[(2s)-2-hydroxy-3-phenylpropoxy]chromen-4-one Chemical compound C([C@@H](O)CC=1C=CC=CC=1)OC(C=1)=CC=C(C2=O)C=1OC=C2C1=CC=C(O)C=C1 VIUAWBLQYVJXIW-IBGZPJMESA-N 0.000 claims description 2
- 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 2
- 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 2
- QPOMIYFFWNHPDD-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[(5-phenyl-1,2-oxazol-3-yl)methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC3=NOC(=C3)C=3C=CC=CC=3)=CC=C2C1=O QPOMIYFFWNHPDD-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- FPUFUYUDPHGFEH-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-(5-pyridin-4-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=CN=CC=3)=CC=C2C1=O FPUFUYUDPHGFEH-UHFFFAOYSA-N 0.000 claims description 2
- XNRHIWZNASULGF-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethoxy]chromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCOC=2C=C3C(C(C(C=4C=CC(O)=CC=4)=CO3)=O)=CC=2)CC1 XNRHIWZNASULGF-UHFFFAOYSA-N 0.000 claims description 2
- VOZPBFARGKFKDU-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-[4-(2-methylphenyl)piperazin-1-yl]ethoxy]chromen-4-one Chemical compound CC1=CC=CC=C1N1CCN(CCOC=2C=C3C(C(C(C=4C=CC(O)=CC=4)=CO3)=O)=CC=2)CC1 VOZPBFARGKFKDU-UHFFFAOYSA-N 0.000 claims description 2
- GKDBURVCBFZSCD-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-[4-(3-methoxyphenyl)piperazin-1-yl]ethoxy]chromen-4-one Chemical compound COC1=CC=CC(N2CCN(CCOC=3C=C4C(C(C(C=5C=CC(O)=CC=5)=CO4)=O)=CC=3)CC2)=C1 GKDBURVCBFZSCD-UHFFFAOYSA-N 0.000 claims description 2
- MVWFUJHZXMTRHS-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-[4-(3-methylphenyl)piperazin-1-yl]ethoxy]chromen-4-one Chemical compound CC1=CC=CC(N2CCN(CCOC=3C=C4C(C(C(C=5C=CC(O)=CC=5)=CO4)=O)=CC=3)CC2)=C1 MVWFUJHZXMTRHS-UHFFFAOYSA-N 0.000 claims description 2
- STVSMLYUQNAJLH-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-[4-(4-methylphenyl)piperazin-1-yl]ethoxy]chromen-4-one Chemical compound C1=CC(C)=CC=C1N1CCN(CCOC=2C=C3C(C(C(C=4C=CC(O)=CC=4)=CO3)=O)=CC=2)CC1 STVSMLYUQNAJLH-UHFFFAOYSA-N 0.000 claims description 2
- KPWVMSRCNSRFBT-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-[4-[2-(trifluoromethyl)phenyl]piperazin-1-yl]ethoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCN3CCN(CC3)C=3C(=CC=CC=3)C(F)(F)F)=CC=C2C1=O KPWVMSRCNSRFBT-UHFFFAOYSA-N 0.000 claims description 2
- HABMRRNWPZNAHB-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-[4-[4-(trifluoromethyl)phenyl]piperazin-1-yl]ethoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCN3CCN(CC3)C=3C=CC(=CC=3)C(F)(F)F)=CC=C2C1=O HABMRRNWPZNAHB-UHFFFAOYSA-N 0.000 claims description 2
- NLBVKHVFWSBBEC-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-[5-(trifluoromethyl)-1h-pyrazol-4-yl]ethoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCC3=C(NN=C3)C(F)(F)F)=CC=C2C1=O NLBVKHVFWSBBEC-UHFFFAOYSA-N 0.000 claims description 2
- QIMFQFMJFVNZFR-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-oxo-2-[4-(trifluoromethyl)phenyl]ethoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC(=O)C=3C=CC(=CC=3)C(F)(F)F)=CC=C2C1=O QIMFQFMJFVNZFR-UHFFFAOYSA-N 0.000 claims description 2
- NVHXGZBXAVVPFO-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[2-[3-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(OC=3)C=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O NVHXGZBXAVVPFO-UHFFFAOYSA-N 0.000 claims description 2
- ZPUVRABODOBSAH-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[3-(trifluoromethoxy)phenyl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3C=C(OC(F)(F)F)C=CC=3)=CC=C2C1=O ZPUVRABODOBSAH-UHFFFAOYSA-N 0.000 claims description 2
- CBQSSDNKQRPHMZ-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[3-(trifluoromethyl)phenyl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O CBQSSDNKQRPHMZ-UHFFFAOYSA-N 0.000 claims description 2
- XZWFEHFXGWFMKS-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[3-[3-(trifluoromethyl)phenyl]-1,2-oxazol-5-yl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3ON=C(C=3)C=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O XZWFEHFXGWFMKS-UHFFFAOYSA-N 0.000 claims description 2
- VFUZTXQSDASORI-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-(2-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methoxy]chromen-4-one Chemical compound COC1=CC=CC=C1C(O1)=NN=C1COC1=CC=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 VFUZTXQSDASORI-UHFFFAOYSA-N 0.000 claims description 2
- RMXOJOGIANOTSJ-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-(2-methylphenyl)-1,3,4-oxadiazol-2-yl]methoxy]chromen-4-one Chemical compound CC1=CC=CC=C1C(O1)=NN=C1COC1=CC=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 RMXOJOGIANOTSJ-UHFFFAOYSA-N 0.000 claims description 2
- PHGCOEMZEZPYOR-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-(3-methoxyphenyl)-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one Chemical compound COC1=CC=CC(C=2ON=C(COC=3C=C4C(C(C(C=5C=CC(O)=CC=5)=CO4)=O)=CC=3)N=2)=C1 PHGCOEMZEZPYOR-UHFFFAOYSA-N 0.000 claims description 2
- FUCKCJMQAGFLIF-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-(3-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methoxy]chromen-4-one Chemical compound COC1=CC=CC(C=2OC(COC=3C=C4C(C(C(C=5C=CC(O)=CC=5)=CO4)=O)=CC=3)=NN=2)=C1 FUCKCJMQAGFLIF-UHFFFAOYSA-N 0.000 claims description 2
- SLDDEMWKXMOGSY-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-(3-methylphenyl)-1,3,4-oxadiazol-2-yl]methoxy]chromen-4-one Chemical compound CC1=CC=CC(C=2OC(COC=3C=C4C(C(C(C=5C=CC(O)=CC=5)=CO4)=O)=CC=3)=NN=2)=C1 SLDDEMWKXMOGSY-UHFFFAOYSA-N 0.000 claims description 2
- SCIHYFZNPVIOOQ-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-(4-methoxyphenyl)-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one Chemical compound C1=CC(OC)=CC=C1C1=NC(COC=2C=C3C(C(C(C=4C=CC(O)=CC=4)=CO3)=O)=CC=2)=NO1 SCIHYFZNPVIOOQ-UHFFFAOYSA-N 0.000 claims description 2
- VQAIBBQEMDSXGR-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methoxy]chromen-4-one Chemical compound C1=CC(OC)=CC=C1C(O1)=NN=C1COC1=CC=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 VQAIBBQEMDSXGR-UHFFFAOYSA-N 0.000 claims description 2
- ZRCYZRQZQQCIAK-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]methoxy]chromen-4-one Chemical compound C1=CC(C)=CC=C1C(O1)=NN=C1COC1=CC=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 ZRCYZRQZQQCIAK-UHFFFAOYSA-N 0.000 claims description 2
- WVGOFTXJQXXJEP-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-[3-(2h-tetrazol-5-yl)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=C(C=CC=3)C=3NN=NN=3)=CC=C2C1=O WVGOFTXJQXXJEP-UHFFFAOYSA-N 0.000 claims description 2
- JUEBRUJMZIBZFF-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-[3-(trifluoromethyl)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=C(C=CC=3)C(F)(F)F)=CC=C2C1=O JUEBRUJMZIBZFF-UHFFFAOYSA-N 0.000 claims description 2
- RKDOJVUCIUGPAG-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-yl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3OC(=NN=3)C=3C=CC(=CC=3)C(F)(F)F)=CC=C2C1=O RKDOJVUCIUGPAG-UHFFFAOYSA-N 0.000 claims description 2
- KRTVXOPDCMVMGC-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-[4-methoxy-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one Chemical compound C1=C(C(F)(F)F)C(OC)=CC=C1C1=NC(COC=2C=C3C(C(C(C=4C=CC(O)=CC=4)=CO3)=O)=CC=2)=NO1 KRTVXOPDCMVMGC-UHFFFAOYSA-N 0.000 claims description 2
- YHHAYEWUUXQFOL-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[6-(trifluoromethyl)pyridin-3-yl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3C=NC(=CC=3)C(F)(F)F)=CC=C2C1=O YHHAYEWUUXQFOL-UHFFFAOYSA-N 0.000 claims description 2
- PKGVXZWMYVCZNT-UHFFFAOYSA-N 3-(4-methoxyphenyl)-7-[[5-(2-methoxyphenyl)-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one Chemical compound C1=CC(OC)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C(=CC=CC=3)OC)=CC=C2C1=O PKGVXZWMYVCZNT-UHFFFAOYSA-N 0.000 claims description 2
- RGQMOEXUFWMRLU-UHFFFAOYSA-N 3-(4-methylphenyl)-7-[[5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one Chemical compound C1=CC(C)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O RGQMOEXUFWMRLU-UHFFFAOYSA-N 0.000 claims description 2
- DRKCCZCIUDIJGT-UHFFFAOYSA-N 3-[3-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]-1,2,4-oxadiazol-5-yl]benzonitrile Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C=CC=3)C#N)=CC=C2C1=O DRKCCZCIUDIJGT-UHFFFAOYSA-N 0.000 claims description 2
- BCHLRGSTGMUSFO-UHFFFAOYSA-N 3-[[3-(4-aminophenyl)-4-oxochromen-7-yl]oxymethyl]benzoic acid Chemical compound C1=CC(N)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C(O)=O)=CC=C2C1=O BCHLRGSTGMUSFO-UHFFFAOYSA-N 0.000 claims description 2
- YAAKJWVORLBNTF-UHFFFAOYSA-N 3-[[3-(4-carbamoylphenyl)-4-oxochromen-7-yl]oxymethyl]benzoic acid Chemical compound C1=CC(C(=O)N)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C(O)=O)=CC=C2C1=O YAAKJWVORLBNTF-UHFFFAOYSA-N 0.000 claims description 2
- DDMANHXIYQTENK-UHFFFAOYSA-N 3-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]-N-[[3-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C(=O)NCC=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O DDMANHXIYQTENK-UHFFFAOYSA-N 0.000 claims description 2
- ATRDANSWHPMPDB-UHFFFAOYSA-N 3-[[3-(4-methylsulfonylphenyl)-4-oxochromen-7-yl]oxymethyl]benzoic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C(O)=O)=CC=C2C1=O ATRDANSWHPMPDB-UHFFFAOYSA-N 0.000 claims description 2
- VFKSORDIMAUFFL-UHFFFAOYSA-N 4-(oxathian-3-yl)morpholine Chemical compound O1SC(CCC1)N1CCOCC1 VFKSORDIMAUFFL-UHFFFAOYSA-N 0.000 claims description 2
- KFLSGMZNSZFNAJ-UHFFFAOYSA-N 4-[4-oxo-7-[[5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]chromen-3-yl]benzonitrile Chemical compound FC(F)(F)C1=CC=CC(C=2ON=C(COC=3C=C4C(C(C(C=5C=CC(=CC=5)C#N)=CO4)=O)=CC=3)N=2)=C1 KFLSGMZNSZFNAJ-UHFFFAOYSA-N 0.000 claims description 2
- QPSPVQPYOAKFBC-UHFFFAOYSA-N 4-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1COC1=CC=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 QPSPVQPYOAKFBC-UHFFFAOYSA-N 0.000 claims description 2
- VFRTZXWTORJKEU-UHFFFAOYSA-N 4-[[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 VFRTZXWTORJKEU-UHFFFAOYSA-N 0.000 claims description 2
- CXIIQPMREFANFO-UHFFFAOYSA-N 6-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-3-(4-hydroxyphenyl)-2-(trifluoromethyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C(C(C1=C2)=O)=C(C(F)(F)F)OC1=CC=C2OCC1=NOC(C=2C=C(C=C(F)C=2)C(F)(F)F)=N1 CXIIQPMREFANFO-UHFFFAOYSA-N 0.000 claims description 2
- RPQZKJITPGRCKF-FQEVSTJZSA-N 7-[(2s)-2-hydroxy-3-[[3-(trifluoromethyl)phenyl]methylamino]propoxy]-3-(4-methoxyphenyl)chromen-4-one Chemical compound C1=CC(OC)=CC=C1C1=COC2=CC(OC[C@@H](O)CNCC=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O RPQZKJITPGRCKF-FQEVSTJZSA-N 0.000 claims description 2
- BHESGBIBNPDUJW-FQEVSTJZSA-N 7-[(2s)-3-[(3,5-difluorophenyl)methylamino]-2-hydroxypropoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C([C@H](O)COC=1C=C2C(C(C(C=3C=CC(O)=CC=3)=CO2)=O)=CC=1)NCC1=CC(F)=CC(F)=C1 BHESGBIBNPDUJW-FQEVSTJZSA-N 0.000 claims description 2
- GUETZOYSPCKXKL-UHFFFAOYSA-N 7-[2-(4-fluorophenyl)-2-oxoethoxy]-3-(4-methoxyphenyl)chromen-4-one Chemical compound C1=CC(OC)=CC=C1C1=COC2=CC(OCC(=O)C=3C=CC(F)=CC=3)=CC=C2C1=O GUETZOYSPCKXKL-UHFFFAOYSA-N 0.000 claims description 2
- KORFTUYYDNQLIT-UHFFFAOYSA-N 7-[2-[3-(5-bromopyridin-3-yl)-1,2,4-oxadiazol-5-yl]ethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCC=3ON=C(N=3)C=3C=C(Br)C=NC=3)=CC=C2C1=O KORFTUYYDNQLIT-UHFFFAOYSA-N 0.000 claims description 2
- YBMCDYRUWGLIEU-UHFFFAOYSA-N 7-[2-[4-(2-fluorophenyl)piperazin-1-yl]ethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCN3CCN(CC3)C=3C(=CC=CC=3)F)=CC=C2C1=O YBMCDYRUWGLIEU-UHFFFAOYSA-N 0.000 claims description 2
- HOPUHQHIURDXAS-UHFFFAOYSA-N 7-[2-[4-(3-fluorophenyl)piperazin-1-yl]ethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCN3CCN(CC3)C=3C=C(F)C=CC=3)=CC=C2C1=O HOPUHQHIURDXAS-UHFFFAOYSA-N 0.000 claims description 2
- LVBYYSGNQQWIJS-UHFFFAOYSA-N 7-[3-[(3,5-difluorophenyl)methylamino]-2-hydroxypropoxy]-3-(4-methoxyphenyl)chromen-4-one Chemical compound C1=CC(OC)=CC=C1C1=COC2=CC(OCC(O)CNCC=3C=C(F)C=C(F)C=3)=CC=C2C1=O LVBYYSGNQQWIJS-UHFFFAOYSA-N 0.000 claims description 2
- TVYQUGOSXLQOGP-UHFFFAOYSA-N 7-[[3-(3-aminophenyl)-1,2,4-oxadiazol-5-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound NC1=CC=CC(C=2N=C(COC=3C=C4C(C(C(C=5C=CC(O)=CC=5)=CO4)=O)=CC=3)ON=2)=C1 TVYQUGOSXLQOGP-UHFFFAOYSA-N 0.000 claims description 2
- IBRIBDVVLALIBW-UHFFFAOYSA-N 7-[[3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl]methoxy]-3-[4-[[3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl]methoxy]phenyl]chromen-4-one Chemical compound FC(F)(F)C1=CC=CC(C=2N=C(COC=3C=CC(=CC=3)C=3C(C4=CC=C(OCC=5ON=C(N=5)C=5C=C(C=CC=5)C(F)(F)F)C=C4OC=3)=O)ON=2)=C1 IBRIBDVVLALIBW-UHFFFAOYSA-N 0.000 claims description 2
- BYZRPKNYQMQCMK-UHFFFAOYSA-N 7-[[3-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3ON=C(N=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O BYZRPKNYQMQCMK-UHFFFAOYSA-N 0.000 claims description 2
- NFLMVGPBVSJOKQ-UHFFFAOYSA-N 7-[[3-fluoro-5-(trifluoromethyl)phenyl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O NFLMVGPBVSJOKQ-UHFFFAOYSA-N 0.000 claims description 2
- WHBOOUQLMQINPB-UHFFFAOYSA-N 7-[[5-(3-chlorophenyl)-1,3,4-oxadiazol-2-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3OC(=NN=3)C=3C=C(Cl)C=CC=3)=CC=C2C1=O WHBOOUQLMQINPB-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- VVVFLKUGSGNQNY-UHFFFAOYSA-N 7-[[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3OC(=NN=3)C=3C=CC(Cl)=CC=3)=CC=C2C1=O VVVFLKUGSGNQNY-UHFFFAOYSA-N 0.000 claims description 2
- TZRVABAXGZCOOH-UHFFFAOYSA-N 7-[[5-[2,5-bis(trifluoromethyl)phenyl]-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=C(C=3)C(F)(F)F)C(F)(F)F)=CC=C2C1=O TZRVABAXGZCOOH-UHFFFAOYSA-N 0.000 claims description 2
- NPGQORNIHHVBJO-UHFFFAOYSA-N 7-[[5-[3,5-bis(trifluoromethyl)phenyl]-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(C=C(C=3)C(F)(F)F)C(F)(F)F)=CC=C2C1=O NPGQORNIHHVBJO-UHFFFAOYSA-N 0.000 claims description 2
- GVOQTGJRDTXIMR-UHFFFAOYSA-N 7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-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(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O GVOQTGJRDTXIMR-UHFFFAOYSA-N 0.000 claims description 2
- CLFPJUWQTLWOEP-UHFFFAOYSA-N 7-[[5-[4-fluoro-3-(trifluoromethyl)phenyl]-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(C(F)=CC=3)C(F)(F)F)=CC=C2C1=O CLFPJUWQTLWOEP-UHFFFAOYSA-N 0.000 claims description 2
- WNYYVTUGJCLMLU-UHFFFAOYSA-N 7-[[6-(trifluoromethyl)pyridin-3-yl]methoxy]-3-[4-[[6-(trifluoromethyl)pyridin-3-yl]methoxy]phenyl]chromen-4-one Chemical compound C1=NC(C(F)(F)F)=CC=C1COC1=CC=C(C=2C(C3=CC=C(OCC=4C=NC(=CC=4)C(F)(F)F)C=C3OC=2)=O)C=C1 WNYYVTUGJCLMLU-UHFFFAOYSA-N 0.000 claims description 2
- HCZBLJIPNULSLU-UHFFFAOYSA-N C1=CC(O)=CC=C1C(OC1=C2)=CC(=O)C1=CC=C2OCCC1=NOC(C=2C=NC=CC=2)=N1 Chemical compound C1=CC(O)=CC=C1C(OC1=C2)=CC(=O)C1=CC=C2OCCC1=NOC(C=2C=NC=CC=2)=N1 HCZBLJIPNULSLU-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims description 2
- WYFVDPDQCBQAHT-UHFFFAOYSA-N N-[7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-4-oxochromen-3-yl]benzamide Chemical compound FC(F)(F)C1=CC(F)=CC(C=2ON=C(COC=3C=C4C(C(C(NC(=O)C=5C=CC=CC=5)=CO4)=O)=CC=3)N=2)=C1 WYFVDPDQCBQAHT-UHFFFAOYSA-N 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 2
- YFTSDZIXAMNCEZ-UHFFFAOYSA-N [3-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]phenyl]boronic acid Chemical compound OB(O)C1=CC=CC(COC=2C=C3C(C(C(C=4C=CC(O)=CC=4)=CO3)=O)=CC=2)=C1 YFTSDZIXAMNCEZ-UHFFFAOYSA-N 0.000 claims description 2
- RPZVGHWHHUBQPE-UHFFFAOYSA-N [4-[7-[2-[3-[2-fluoro-4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl]ethoxy]-4-oxochromen-3-yl]phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=COC2=CC(OCCC=3ON=C(N=3)C=3C(=CC(=CC=3)C(F)(F)F)F)=CC=C2C1=O RPZVGHWHHUBQPE-UHFFFAOYSA-N 0.000 claims description 2
- NDJFEYMUZIFTRQ-UHFFFAOYSA-N [4-[7-[[5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl]methoxy]-4-oxochromen-3-yl]phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=CC(F)=CC=3)=CC=C2C1=O NDJFEYMUZIFTRQ-UHFFFAOYSA-N 0.000 claims description 2
- VIICMKGBRBRXRG-UHFFFAOYSA-N [4-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1COC1=CC=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 VIICMKGBRBRXRG-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 claims description 2
- 229960003920 cocaine Drugs 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- HTFFABIIOAKIBH-UHFFFAOYSA-N diazinane Chemical compound C1CCNNC1 HTFFABIIOAKIBH-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 206010013663 drug dependence Diseases 0.000 claims description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 2
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 claims description 2
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- SZYSQGBOCVSYQS-UHFFFAOYSA-N n-(4-fluorophenyl)-4-[2-[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyethyl]piperazine-1-carbothioamide Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCN3CCN(CC3)C(=S)NC=3C=CC(F)=CC=3)=CC=C2C1=O SZYSQGBOCVSYQS-UHFFFAOYSA-N 0.000 claims description 2
- KDHZOCWAWMYCJB-UHFFFAOYSA-N n-[3-[7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-4-oxochromen-3-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C=2C(C3=CC=C(OCC=4N=C(ON=4)C=4C=C(C=C(F)C=4)C(F)(F)F)C=C3OC=2)=O)=C1 KDHZOCWAWMYCJB-UHFFFAOYSA-N 0.000 claims description 2
- IYWMHWZYYBEMLX-UHFFFAOYSA-N n-[4-[4-oxo-7-[[2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-4-yl]methoxy]chromen-3-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3N=C(SC=3)C=3C=CC(=CC=3)C(F)(F)F)=CC=C2C1=O IYWMHWZYYBEMLX-UHFFFAOYSA-N 0.000 claims description 2
- XRXFUBQZEAXFBU-UHFFFAOYSA-N n-[4-[4-oxo-7-[[3-(trifluoromethoxy)phenyl]methoxy]chromen-3-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3C=C(OC(F)(F)F)C=CC=3)=CC=C2C1=O XRXFUBQZEAXFBU-UHFFFAOYSA-N 0.000 claims description 2
- DYOALZKAPRMVKL-UHFFFAOYSA-N n-[4-[4-oxo-7-[[3-(trifluoromethyl)phenyl]methoxy]chromen-3-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O DYOALZKAPRMVKL-UHFFFAOYSA-N 0.000 claims description 2
- ARHPCVRPEMHVFN-UHFFFAOYSA-N n-[4-[4-oxo-7-[[5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]chromen-3-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O ARHPCVRPEMHVFN-UHFFFAOYSA-N 0.000 claims description 2
- OZIYZNIPBGCGKS-UHFFFAOYSA-N n-[4-[7-[2-[3-[2-fluoro-4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl]ethoxy]-4-oxochromen-3-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCCC=3ON=C(N=3)C=3C(=CC(=CC=3)C(F)(F)F)F)=CC=C2C1=O OZIYZNIPBGCGKS-UHFFFAOYSA-N 0.000 claims description 2
- TULOYQLETVYVIG-UHFFFAOYSA-N n-[[4-chloro-3-(trifluoromethyl)phenyl]methyl]-3-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]benzamide Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C(=O)NCC=3C=C(C(Cl)=CC=3)C(F)(F)F)=CC=C2C1=O TULOYQLETVYVIG-UHFFFAOYSA-N 0.000 claims description 2
- 229960002715 nicotine Drugs 0.000 claims description 2
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 2
- 229940127240 opiate Drugs 0.000 claims description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 2
- 150000004866 oxadiazoles Chemical class 0.000 claims description 2
- 150000002916 oxazoles Chemical class 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229950000688 phenothiazine Drugs 0.000 claims description 2
- DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical compound CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 0.000 claims description 2
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 claims description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 2
- 150000003222 pyridines Chemical class 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 2
- 208000011117 substance-related disease Diseases 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 claims description 2
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims description 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 2
- 150000003557 thiazoles Chemical class 0.000 claims description 2
- 125000005505 thiomorpholino group Chemical group 0.000 claims description 2
- 101100240527 Caenorhabditis elegans nhr-22 gene Proteins 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 claims 1
- 150000002462 imidazolines Chemical class 0.000 claims 1
- ZSVHUITUMSDFCK-UHFFFAOYSA-N isoquinoline;quinoline Chemical compound C1=NC=CC2=CC=CC=C21.N1=CC=CC2=CC=CC=C21 ZSVHUITUMSDFCK-UHFFFAOYSA-N 0.000 claims 1
- YBSGKKITPLSUPH-HXUWFJFHSA-N 3-(4-hydroxyphenyl)-7-[(2r)-2-hydroxy-3-[[3-(trifluoromethyl)phenyl]methylamino]propoxy]chromen-4-one Chemical compound C([C@@H](O)COC=1C=C2C(C(C(C=3C=CC(O)=CC=3)=CO2)=O)=CC=1)NCC1=CC=CC(C(F)(F)F)=C1 YBSGKKITPLSUPH-HXUWFJFHSA-N 0.000 description 2
- BHESGBIBNPDUJW-HXUWFJFHSA-N 7-[(2r)-3-[(3,5-difluorophenyl)methylamino]-2-hydroxypropoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C([C@@H](O)COC=1C=C2C(C(C(C=3C=CC(O)=CC=3)=CO2)=O)=CC=1)NCC1=CC(F)=CC(F)=C1 BHESGBIBNPDUJW-HXUWFJFHSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 1
- QXODMLJSSSYMLK-UHFFFAOYSA-N 2-[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy-n-[2-(trifluoromethyl)phenyl]acetamide Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC(=O)NC=3C(=CC=CC=3)C(F)(F)F)=CC=C2C1=O QXODMLJSSSYMLK-UHFFFAOYSA-N 0.000 description 1
- NNJIPLNZQWTZBZ-UHFFFAOYSA-N 2-[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyacetonitrile Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC#N)=CC=C2C1=O NNJIPLNZQWTZBZ-UHFFFAOYSA-N 0.000 description 1
- NSXHBSIIXXOEJZ-UHFFFAOYSA-N 2-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]-1,3-oxazole-5-carboxylic acid Chemical compound O1C(C(=O)O)=CN=C1COC1=CC=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 NSXHBSIIXXOEJZ-UHFFFAOYSA-N 0.000 description 1
- OOZFVAKRVNCKET-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-2-(trifluoromethyl)-7-[[5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=C(C(F)(F)F)OC2=CC(OCC=3N=C(ON=3)C=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O OOZFVAKRVNCKET-UHFFFAOYSA-N 0.000 description 1
- AFPWFAXOBKZWFY-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[(2-phenyl-1,3-oxazol-5-yl)methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3OC(=NC=3)C=3C=CC=CC=3)=CC=C2C1=O AFPWFAXOBKZWFY-UHFFFAOYSA-N 0.000 description 1
- VIUAWBLQYVJXIW-LJQANCHMSA-N 3-(4-hydroxyphenyl)-7-[(2r)-2-hydroxy-3-phenylpropoxy]chromen-4-one Chemical compound C([C@H](O)CC=1C=CC=CC=1)OC(C=1)=CC=C(C2=O)C=1OC=C2C1=CC=C(O)C=C1 VIUAWBLQYVJXIW-LJQANCHMSA-N 0.000 description 1
- 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 description 1
- YBSGKKITPLSUPH-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-hydroxy-3-[[3-(trifluoromethyl)phenyl]methylamino]propoxy]chromen-4-one Chemical compound C=1C=C(C(C(C=2C=CC(O)=CC=2)=CO2)=O)C2=CC=1OCC(O)CNCC1=CC=CC(C(F)(F)F)=C1 YBSGKKITPLSUPH-UHFFFAOYSA-N 0.000 description 1
- KVLGZHXMDKNCSJ-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3SC(=NC=3)C=3C=CC(=CC=3)C(F)(F)F)=CC=C2C1=O KVLGZHXMDKNCSJ-UHFFFAOYSA-N 0.000 description 1
- JDRLUTQDZBMYTM-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-(trifluoromethyl)pyridin-3-yl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3C=C(C=NC=3)C(F)(F)F)=CC=C2C1=O JDRLUTQDZBMYTM-UHFFFAOYSA-N 0.000 description 1
- OETXYXJPMCXLGD-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[[3-(trifluoromethyl)phenyl]methylamino]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCNCC=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O OETXYXJPMCXLGD-UHFFFAOYSA-N 0.000 description 1
- HUMHXLIXFLWZNP-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)-7-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methoxy]chromen-4-one Chemical compound C1=NC(OC)=CC=C1C1=COC2=CC(OCC3=C(N=C(S3)C=3C=CC(=CC=3)C(F)(F)F)C)=CC=C2C1=O HUMHXLIXFLWZNP-UHFFFAOYSA-N 0.000 description 1
- KAHNJRAGQDDUMW-UHFFFAOYSA-N 3-[2,4-bis[(2-methylpropan-2-yl)oxy]pyrimidin-5-yl]-7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one Chemical compound CC(C)(C)OC1=NC(OC(C)(C)C)=NC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O KAHNJRAGQDDUMW-UHFFFAOYSA-N 0.000 description 1
- VZMYKSGRMWHSTC-UHFFFAOYSA-N 4-[4-oxo-7-[[3-[3-(trifluoromethyl)phenyl]-1,2-oxazol-5-yl]methoxy]chromen-3-yl]benzonitrile Chemical compound FC(F)(F)C1=CC=CC(C2=NOC(COC=3C=C4C(C(C(C=5C=CC(=CC=5)C#N)=CO4)=O)=CC=3)=C2)=C1 VZMYKSGRMWHSTC-UHFFFAOYSA-N 0.000 description 1
- QYVQTNWRQXUXJF-UHFFFAOYSA-N 4-[7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-yl]methoxy]-4-oxochromen-3-yl]benzonitrile Chemical compound FC(F)(F)C1=CC(F)=CC(C=2OC(COC=3C=C4C(C(C(C=5C=CC(=CC=5)C#N)=CO4)=O)=CC=3)=NN=2)=C1 QYVQTNWRQXUXJF-UHFFFAOYSA-N 0.000 description 1
- FINMWZYOOYZFFV-UHFFFAOYSA-N 4-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]-7-methoxychromen-2-one Chemical compound C=1C(=O)OC2=CC(OC)=CC=C2C=1COC(C=1)=CC=C(C2=O)C=1OC=C2C1=CC=C(O)C=C1 FINMWZYOOYZFFV-UHFFFAOYSA-N 0.000 description 1
- YHAORQQIHFPGRQ-UHFFFAOYSA-N 5-[4-[7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-4-oxochromen-3-yl]phenyl]-1,3-diazinane-2,4-dione Chemical compound FC(F)(F)C1=CC(F)=CC(C=2ON=C(COC=3C=C4C(C(C(C=5C=CC(=CC=5)C5C(NC(=O)NC5)=O)=CO4)=O)=CC=3)N=2)=C1 YHAORQQIHFPGRQ-UHFFFAOYSA-N 0.000 description 1
- LIMLEVSJNWTFGC-UHFFFAOYSA-N 5-[7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-4-oxochromen-3-yl]-1h-pyrimidine-2,4-dione Chemical compound FC(F)(F)C1=CC(F)=CC(C=2ON=C(COC=3C=C4C(C(C(C=5C(NC(=O)NC=5)=O)=CO4)=O)=CC=3)N=2)=C1 LIMLEVSJNWTFGC-UHFFFAOYSA-N 0.000 description 1
- HALZFZWMHAVEKJ-UHFFFAOYSA-N 7-(pyridin-2-ylmethoxy)-3-[4-(pyridin-2-ylmethoxy)phenyl]chromen-4-one Chemical compound C=1C=C2C(=O)C(C=3C=CC(OCC=4N=CC=CC=4)=CC=3)=COC2=CC=1OCC1=CC=CC=N1 HALZFZWMHAVEKJ-UHFFFAOYSA-N 0.000 description 1
- GBPXKSUYGHTFAK-UHFFFAOYSA-N 7-[2-[2-[3-fluoro-5-(trifluoromethyl)phenyl]-1,3-oxazol-5-yl]ethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCC=3OC(=NC=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O GBPXKSUYGHTFAK-UHFFFAOYSA-N 0.000 description 1
- BHESGBIBNPDUJW-UHFFFAOYSA-N 7-[3-[(3,5-difluorophenyl)methylamino]-2-hydroxypropoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C=1C=C(C(C(C=2C=CC(O)=CC=2)=CO2)=O)C2=CC=1OCC(O)CNCC1=CC(F)=CC(F)=C1 BHESGBIBNPDUJW-UHFFFAOYSA-N 0.000 description 1
- VNNSFXKBYWVKED-UHFFFAOYSA-N 7-[3-[4-(4-chlorophenyl)-1h-pyrazol-5-yl]propoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCCC=3C(=CNN=3)C=3C=CC(Cl)=CC=3)=CC=C2C1=O VNNSFXKBYWVKED-UHFFFAOYSA-N 0.000 description 1
- XKTXUAMEECZDAD-MRXNPFEDSA-N 7-[3-[[(1r)-1-(4-fluorophenyl)ethyl]amino]-2-oxopropoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound N([C@H](C)C=1C=CC(F)=CC=1)CC(=O)COC(C=1)=CC=C(C2=O)C=1OC=C2C1=CC=C(O)C=C1 XKTXUAMEECZDAD-MRXNPFEDSA-N 0.000 description 1
- YQJGDFSWAKPWKP-UHFFFAOYSA-N 7-[[5-(2-chlorophenyl)-1,3,4-thiadiazol-2-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3SC(=NN=3)C=3C(=CC=CC=3)Cl)=CC=C2C1=O YQJGDFSWAKPWKP-UHFFFAOYSA-N 0.000 description 1
- OHLICEDYIMGQJJ-UHFFFAOYSA-N 7-[[5-(3-aminophenyl)-1,3,4-oxadiazol-2-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound NC1=CC=CC(C=2OC(COC=3C=C4C(C(C(C=5C=CC(O)=CC=5)=CO4)=O)=CC=3)=NN=2)=C1 OHLICEDYIMGQJJ-UHFFFAOYSA-N 0.000 description 1
- ARGNGSMWKBQUHD-UHFFFAOYSA-N 7-[[5-(trifluoromethyl)pyridin-3-yl]methoxy]-3-[4-[[6-(trifluoromethyl)pyridin-3-yl]methoxy]phenyl]chromen-4-one Chemical compound FC(F)(F)C1=CN=CC(COC=2C=C3C(C(C(C=4C=CC(OCC=5C=NC(=CC=5)C(F)(F)F)=CC=4)=CO3)=O)=CC=2)=C1 ARGNGSMWKBQUHD-UHFFFAOYSA-N 0.000 description 1
- QYQKUUSGCMRSCO-UHFFFAOYSA-N 7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-3-(1h-indazol-5-yl)chromen-4-one Chemical compound FC(F)(F)C1=CC(F)=CC(C=2ON=C(COC=3C=C4C(C(C(C=5C=C6C=NNC6=CC=5)=CO4)=O)=CC=3)N=2)=C1 QYQKUUSGCMRSCO-UHFFFAOYSA-N 0.000 description 1
- BWYTYTZPQHKLAL-UHFFFAOYSA-N 7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-3-(4-morpholin-4-ylphenyl)chromen-4-one Chemical compound FC(F)(F)C1=CC(F)=CC(C=2ON=C(COC=3C=C4C(C(C(C=5C=CC(=CC=5)N5CCOCC5)=CO4)=O)=CC=3)N=2)=C1 BWYTYTZPQHKLAL-UHFFFAOYSA-N 0.000 description 1
- QRYRMWAXXGGTJJ-UHFFFAOYSA-N 7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-3-(6-methoxypyridin-3-yl)chromen-4-one Chemical compound C1=NC(OC)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O QRYRMWAXXGGTJJ-UHFFFAOYSA-N 0.000 description 1
- LHFWZVAHDFOEGQ-UHFFFAOYSA-N 7-[[5-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-4-yl]methoxy]-3-(4-morpholin-4-ylphenyl)chromen-4-one Chemical compound CC=1SC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1COC(C=1)=CC=C(C2=O)C=1OC=C2C(C=C1)=CC=C1N1CCOCC1 LHFWZVAHDFOEGQ-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- AMJINJSTVXQTMD-UHFFFAOYSA-N [4-[7-[[2-[3-fluoro-5-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]methoxy]-4-oxochromen-3-yl]phenyl] dihydrogen phosphate Chemical compound C1=CC(OP(O)(=O)O)=CC=C1C1=COC2=CC(OCC=3N=C(OC=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O AMJINJSTVXQTMD-UHFFFAOYSA-N 0.000 description 1
- 229940025084 amphetamine Drugs 0.000 description 1
- UXSGCFFGBFFORL-UHFFFAOYSA-N methyl 2-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]-1,3-oxazole-5-carboxylate Chemical compound O1C(C(=O)OC)=CN=C1COC1=CC=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 UXSGCFFGBFFORL-UHFFFAOYSA-N 0.000 description 1
- DABNYYYHTLVHIY-UHFFFAOYSA-N n-(3-fluorophenyl)-4-[2-[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyethyl]piperazine-1-carbothioamide Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCN3CCN(CC3)C(=S)NC=3C=C(F)C=CC=3)=CC=C2C1=O DABNYYYHTLVHIY-UHFFFAOYSA-N 0.000 description 1
- IIMPDNKAFMXDQT-UHFFFAOYSA-N n-[4-[4-oxo-7-[[2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methoxy]chromen-3-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3SC(=NC=3)C=3C=CC(=CC=3)C(F)(F)F)=CC=C2C1=O IIMPDNKAFMXDQT-UHFFFAOYSA-N 0.000 description 1
- XFZMWSGJOVSFQL-UHFFFAOYSA-N n-[4-[7-[[3-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl]methoxy]-4-oxochromen-3-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3ON=C(N=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O XFZMWSGJOVSFQL-UHFFFAOYSA-N 0.000 description 1
- JHCGGPAVJCDDST-UHFFFAOYSA-N prop-2-enyl 3-[[3-(4-aminophenyl)-4-oxochromen-7-yl]oxymethyl]benzoate Chemical compound C1=CC(N)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C(=O)OCC=C)=CC=C2C1=O JHCGGPAVJCDDST-UHFFFAOYSA-N 0.000 description 1
- GDYRXRZDLNWLAV-UHFFFAOYSA-N prop-2-enyl 3-[[3-[4-(methanesulfonamido)phenyl]-4-oxochromen-7-yl]oxymethyl]benzoate Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C(=O)OCC=C)=CC=C2C1=O GDYRXRZDLNWLAV-UHFFFAOYSA-N 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83408306P | 2006-07-27 | 2006-07-27 | |
| US84642806P | 2006-09-21 | 2006-09-21 | |
| PCT/US2007/074665 WO2008014497A2 (en) | 2006-07-27 | 2007-07-27 | Aldh-2 inhibitors in the treatment of addiction |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009544742A JP2009544742A (ja) | 2009-12-17 |
| JP2009544742A5 true JP2009544742A5 (enExample) | 2010-10-07 |
Family
ID=38792141
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009522029A Withdrawn JP2009544742A (ja) | 2006-07-27 | 2007-07-27 | 嗜癖の治療におけるａｌｄｈ−２阻害剤 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US20080032995A1 (enExample) |
| EP (1) | EP2046769A2 (enExample) |
| JP (1) | JP2009544742A (enExample) |
| KR (1) | KR20090033417A (enExample) |
| AU (1) | AU2007278877A1 (enExample) |
| CA (1) | CA2653056A1 (enExample) |
| CO (1) | CO6210811A2 (enExample) |
| EC (1) | ECSP088919A (enExample) |
| IL (1) | IL195400A0 (enExample) |
| MA (1) | MA30434B1 (enExample) |
| MX (1) | MX2008015765A (enExample) |
| NO (1) | NO20084971L (enExample) |
| RU (1) | RU2008151762A (enExample) |
| WO (1) | WO2008014497A2 (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080207610A1 (en) * | 2006-07-27 | 2008-08-28 | Jeff Zablocki | Aldh-2 inhibitors in the treatment of addiction |
| US8158810B2 (en) * | 2006-07-27 | 2012-04-17 | Gilead Sciences, Inc. | ALDH-2 inhibitors in the treatment of addiction |
| JO3598B1 (ar) | 2006-10-10 | 2020-07-05 | Infinity Discovery Inc | الاحماض والاسترات البورونية كمثبطات اميد هيدروليز الحامض الدهني |
| WO2008112164A2 (en) | 2007-03-08 | 2008-09-18 | The Board Of Trustees Of The Leland Stanford Junior University | Mitochondrial aldehyde dehydrogenase-2 modulators and methods of use thereof |
| CA2682207A1 (en) | 2007-04-05 | 2008-10-16 | Cv Therapeutics, Inc. | Quinazolinone derivatives as aldh-2 inhibitors |
| EP2231149A2 (en) * | 2007-11-06 | 2010-09-29 | CV Therapeutics Inc. | Aldh-2 inhibitors in the treatment of psychiatric disorders |
| JP2011510072A (ja) * | 2008-01-24 | 2011-03-31 | ギリアード・パロ・アルト・インコーポレイテッド | 嗜癖の処置におけるａｌｄｈ−２インヒビター |
| BRPI0908428A2 (pt) * | 2008-02-06 | 2015-12-08 | Gilead Sciences Inc | uso de ranozalina para tratar a dor. |
| AU2009233711B2 (en) | 2008-04-09 | 2015-02-12 | Infinity Pharmaceuticals, Inc | Inhibitors of fatty acid amide hydrolase |
| WO2010028175A1 (en) | 2008-09-08 | 2010-03-11 | The Board Of Trustees Of The Leland Stanford Junior University | Modulators of aldehyde dehydrogenase activity and methods of use thereof |
| JP2012506856A (ja) * | 2008-10-28 | 2012-03-22 | ボード オブ トラスティーズ オブ ザ レランド スタンフォード ジュニア ユニバーシティ | アルデヒドデヒドロゲナーゼのモジュレーターおよびその使用方法 |
| EP2340292B1 (de) * | 2008-10-29 | 2013-05-29 | Merck Patent GmbH | Flüssigkristallanzeige |
| WO2010118159A1 (en) | 2009-04-07 | 2010-10-14 | Infinity Pharmaceuticals, Inc. | Inhibitors of fatty acid amide hydrolase |
| WO2010118155A1 (en) | 2009-04-07 | 2010-10-14 | Infinity Pharmaceuticals, Inc. | Inhibitors of fatty acid amide hydrolase |
| BR112012019120A2 (pt) | 2010-02-03 | 2016-06-28 | Infinity Pharmaceuticais Inc | forma sólida, composição farmacêutica, método de preparação do composto 1, método de tratamento de uma condição mediada por faah |
| SI2533638T1 (sl) * | 2010-02-12 | 2016-05-31 | Nivalis Therapeutics, Inc. | Novi inhibitorji S-nitrozoglutation reduktaze |
| WO2012149106A1 (en) | 2011-04-29 | 2012-11-01 | The Board Of Trustees Of The Leland Stanford Junior University | Compositions and methods for increasing proliferation of adult salivary stem cells |
| TWI567061B (zh) | 2011-07-01 | 2017-01-21 | 吉李德科學股份有限公司 | 用於治療成癮之化合物 |
| KR20150135332A (ko) | 2013-03-14 | 2015-12-02 | 더 보드 오브 트러스티스 오브 더 리랜드 스탠포드 쥬니어 유니버시티 | 미토콘드리아 알데히드 탈수소효소-2 조절인자들 및 이들의 사용 방법 |
| US9063420B2 (en) | 2013-07-16 | 2015-06-23 | Rohm And Haas Electronic Materials Llc | Photoresist composition, coated substrate, and method of forming electronic device |
| US9410016B2 (en) | 2013-07-16 | 2016-08-09 | Dow Global Technologies Llc | Aromatic polyacetals and articles comprising them |
| US8933239B1 (en) | 2013-07-16 | 2015-01-13 | Dow Global Technologies Llc | Bis(aryl)acetal compounds |
| US8962779B2 (en) | 2013-07-16 | 2015-02-24 | Dow Global Technologies Llc | Method of forming polyaryl polymers |
| WO2019079209A1 (en) * | 2017-10-16 | 2019-04-25 | Amygdala Neurosciences, Inc. | POLYTHERAPY FOR THE PREVENTION OF AN ADDICTION |
| JP7204568B2 (ja) * | 2018-04-04 | 2023-01-16 | 株式会社Cics | アミロイドβ疾患のホウ素中性子捕捉療法用化合物 |
| CN109970738B (zh) * | 2019-02-27 | 2021-07-09 | 上海工程技术大学 | 一种金雀花碱n-异黄酮类化合物及其制备方法及应用 |
| EP4540228A1 (en) | 2022-06-14 | 2025-04-23 | Amygdala Neurosciences, Inc. | Aldh-2 inhibitor compounds and methods of use |
| JP2025520426A (ja) | 2022-06-14 | 2025-07-03 | アミグダラ ニューロサイエンシーズ， インコーポレイテッド | Ａｌｄｈ－２阻害化合物及び使用方法 |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3907830A (en) * | 1970-05-27 | 1975-09-23 | Chinoin Gyogyszer Es Vegyeszet | Isoflavone derivatives |
| US4166862A (en) * | 1971-05-25 | 1979-09-04 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt. | Animal feed containing anabolic isoflavones |
| US3845770A (en) | 1972-06-05 | 1974-11-05 | Alza Corp | Osmatic dispensing device for releasing beneficial agent |
| DE2950135A1 (de) * | 1979-12-13 | 1981-06-19 | Merck Patent Gmbh, 6100 Darmstadt | Basischer aether, diese enthaltende pharmazeutische zubereitungen und verfahren zu ihrer herstellung |
| US4326525A (en) | 1980-10-14 | 1982-04-27 | Alza Corporation | Osmotic device that improves delivery properties of agent in situ |
| US5364620A (en) | 1983-12-22 | 1994-11-15 | Elan Corporation, Plc | Controlled absorption diltiazem formulation for once daily administration |
| JPS62201882A (ja) * | 1985-11-18 | 1987-09-05 | Yamanouchi Pharmaceut Co Ltd | イソフラボン誘導体 |
| US5023252A (en) | 1985-12-04 | 1991-06-11 | Conrex Pharmaceutical Corporation | Transdermal and trans-membrane delivery of drugs |
| US4992445A (en) | 1987-06-12 | 1991-02-12 | American Cyanamid Co. | Transdermal delivery of pharmaceuticals |
| US5001139A (en) | 1987-06-12 | 1991-03-19 | American Cyanamid Company | Enchancers for the transdermal flux of nivadipine |
| US4902514A (en) | 1988-07-21 | 1990-02-20 | Alza Corporation | Dosage form for administering nilvadipine for treating cardiovascular symptoms |
| US5204369A (en) * | 1991-07-01 | 1993-04-20 | The Endowment For Research In Human Biology | Method for the inhibition of aldh-i useful in the treatment of alcohol dependence or alcohol abuse |
| US5679806A (en) * | 1995-02-24 | 1997-10-21 | Hauser, Inc. | Process for the isolation and purification of isoflavones |
| US5783189A (en) * | 1996-04-23 | 1998-07-21 | Natural Pharmacia International, Inc. | Method for treating alcohol dependence |
| US6255497B1 (en) * | 1997-04-29 | 2001-07-03 | The Endowment For Research In Human Biology, Inc. | Method for the inhibition of ALDH-I useful in the treatment of alcohol dependence or alcohol abuse |
| AU3899199A (en) | 1998-05-12 | 1999-11-29 | Endowment for Research in Human Biology, Inc., The | Methods and assays useful in the treatment of alcohol dependence or alcohol abuse |
| WO2004001058A2 (en) * | 2001-05-04 | 2003-12-31 | Paratek Pharmaceuticals, Inc. | Transcription factor modulating compounds and methods of use thereof |
| MXPA05000122A (es) * | 2002-06-27 | 2005-12-14 | Endowment For Res In Human Bio | Compuestos utiles para la inhibicion de aldehido-deshidrogenasa. |
| CA2571421A1 (en) * | 2004-06-24 | 2006-01-05 | Nicholas Valiante | Compounds for immunopotentiation |
| US8158810B2 (en) * | 2006-07-27 | 2012-04-17 | Gilead Sciences, Inc. | ALDH-2 inhibitors in the treatment of addiction |
| US20080207610A1 (en) * | 2006-07-27 | 2008-08-28 | Jeff Zablocki | Aldh-2 inhibitors in the treatment of addiction |
| CA2682207A1 (en) * | 2007-04-05 | 2008-10-16 | Cv Therapeutics, Inc. | Quinazolinone derivatives as aldh-2 inhibitors |
| EP2231149A2 (en) * | 2007-11-06 | 2010-09-29 | CV Therapeutics Inc. | Aldh-2 inhibitors in the treatment of psychiatric disorders |
-
2007
- 2007-07-27 RU RU2008151762/04A patent/RU2008151762A/ru unknown
- 2007-07-27 MX MX2008015765A patent/MX2008015765A/es not_active Application Discontinuation
- 2007-07-27 WO PCT/US2007/074665 patent/WO2008014497A2/en not_active Ceased
- 2007-07-27 KR KR1020087029279A patent/KR20090033417A/ko not_active Withdrawn
- 2007-07-27 EP EP07813501A patent/EP2046769A2/en not_active Withdrawn
- 2007-07-27 JP JP2009522029A patent/JP2009544742A/ja not_active Withdrawn
- 2007-07-27 US US11/829,836 patent/US20080032995A1/en not_active Abandoned
- 2007-07-27 CA CA002653056A patent/CA2653056A1/en not_active Abandoned
- 2007-07-27 AU AU2007278877A patent/AU2007278877A1/en not_active Abandoned
-
2008
- 2008-11-20 IL IL195400A patent/IL195400A0/en unknown
- 2008-11-26 NO NO20084971A patent/NO20084971L/no not_active Application Discontinuation
- 2008-11-27 MA MA31422A patent/MA30434B1/fr unknown
- 2008-11-28 EC EC2008008919A patent/ECSP088919A/es unknown
- 2008-12-29 CO CO08137618A patent/CO6210811A2/es not_active Application Discontinuation
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2008151762A (ru) | Adlh-2 ингибиторы для лечения аддикции | |
| RU2010122970A (ru) | Ингибиторы aldh-2 при лечении психиатрических расстройств | |
| ES2660571T3 (es) | Inhibidores de la proteína tirosina fosfatasa humana y su uso farmacéutico | |
| RU2492167C2 (ru) | Производные аминотриазола в качестве агонистов alх | |
| JP5261383B2 (ja) | ヒトプロテインチロシンホスファターゼ阻害剤および使用法 | |
| JP2015533157A5 (enExample) | ||
| JP2013519680A5 (enExample) | ||
| CA2583217A1 (en) | 1,3,4-thiadiazole compounds as protein kinase inhibitors | |
| JP2019517455A5 (enExample) | ||
| JP2019052178A (ja) | ブロモドメイン阻害剤としての新規の置換された二環式化合物 | |
| RU2018138707A (ru) | Замещенные гетероарилом пиридины и способы применения | |
| TWI705963B (zh) | 作為ｄｙｒｋ激酶抑制劑之2,3-二氫苯并呋喃-5-基化合物 | |
| JP2009525984A5 (enExample) | ||
| JP2006503010A5 (enExample) | ||
| JP2018534328A5 (enExample) | ||
| HRP20120281T1 (hr) | Derivati azabiciklo[3.1.0]heksana, korisni kao modulatori dopaminskih receptora d3 | |
| JP2012513958A (ja) | １，２，４−オキサジアゾール誘導体およびそれらの治療的使用 | |
| JP2020520354A5 (enExample) | ||
| RU2016111138A (ru) | Гетероциклические соединения и способы их применения | |
| JP2007523208A5 (enExample) | ||
| RU2012134306A (ru) | Азотосодержащие производные гетероарилов | |
| JP2011510985A5 (enExample) | ||
| JP2018507234A5 (enExample) | ||
| JP2014523400A5 (enExample) | ||
| JP2020073539A (ja) | 線維症を処置するための方法及び医薬組成物 |