JP2009544742A5 - - Google Patents
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- 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- Withdrawn
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- 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
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| US20080207610A1 (en) * | 2006-07-27 | 2008-08-28 | Jeff Zablocki | 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 |
| EP2126574B1 (en) | 2007-03-08 | 2015-12-23 | The Board of Trustees of the Leland Stanford Junior University | Mitochondrial aldehyde dehydrogenase-2 modulators and methods of use thereof |
| EP2129665A1 (en) | 2007-04-05 | 2009-12-09 | CV Therapeutics Inc. | Quinazolinone derivatives as aldh-2 inhibitors |
| AU2008323953A1 (en) * | 2007-11-06 | 2009-05-14 | Gilead Palo Alto, Inc. | ALDH-2 inhibitors in the treatment of psychiatric disorders |
| MX2010008111A (es) * | 2008-01-24 | 2010-11-30 | Endowment For Res In Human Biology Inc | Inhibidores de aldh-2 en el tratamiento de adicciones. |
| CA2713521A1 (en) * | 2008-02-06 | 2009-08-13 | Gilead Palo Alto, Inc. | Use of ranolazine for treating pain |
| CN102046179B (zh) | 2008-04-09 | 2015-01-14 | 英菲尼提制药公司 | 脂肪酸酰胺水解酶抑制剂 |
| 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 |
| EP2349279A4 (en) | 2008-10-28 | 2013-12-25 | Univ Leland Stanford Junior | MODIFIERS OF ALDEHYDE DEHYDROGENASE AND METHODS OF USE THEREOF |
| WO2010049044A1 (de) * | 2008-10-29 | 2010-05-06 | Merck Patent Gmbh | Flüssigkristallanzeige |
| US8546564B2 (en) | 2009-04-07 | 2013-10-01 | Infinity Pharmaceuticals, Inc. | Inhibitors of fatty acid amide hydrolase |
| AU2010234449A1 (en) | 2009-04-07 | 2011-11-03 | Infinity Pharmaceuticals, Inc. | Inhibitors of fatty acid amide hydrolase |
| JP2013518886A (ja) | 2010-02-03 | 2013-05-23 | インフイニトイ プハルマセウトイカルス インコーポレイテッド | 脂肪酸アミドヒドロラーゼ阻害剤 |
| WO2011100433A1 (en) * | 2010-02-12 | 2011-08-18 | N30 Pharmaceuticals, Llc | Novel s-nitrosoglutathione reductase inhibitors |
| 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 |
| US8962779B2 (en) | 2013-07-16 | 2015-02-24 | Dow Global Technologies Llc | Method of forming polyaryl polymers |
| US8933239B1 (en) | 2013-07-16 | 2015-01-13 | Dow Global Technologies Llc | Bis(aryl)acetal compounds |
| US9410016B2 (en) | 2013-07-16 | 2016-08-09 | Dow Global Technologies Llc | Aromatic polyacetals and articles comprising them |
| 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 |
| WO2023244574A1 (en) | 2022-06-14 | 2023-12-21 | Amygdala Neurosciences, Inc. | Aldh-2 inhibitor compounds and methods of use |
| CA3259203A1 (en) | 2022-06-14 | 2023-12-21 | Amygdala Neurosciences, Inc. | ALDH-2 INHIBITING COMPOUNDS AND METHODS OF USE |
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| 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 |
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| 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 |
| US6121010A (en) * | 1998-05-12 | 2000-09-19 | The Endowment For Research In Human Biology | Methods and assays useful in the treatment of alcohol dependence or alcohol abuse |
| CA2445515A1 (en) * | 2001-05-04 | 2002-11-04 | Paratek Pharmaceuticals, Inc. | Transcription factor modulating compounds and methods of use thereof |
| KR20060011785A (ko) * | 2002-06-27 | 2006-02-03 | 디 인다우먼트 포 리써치 인 휴먼 바이올로지, 인크. | Ａｌｄｈ 억제에 유용한 화합물 |
| WO2006002422A2 (en) * | 2004-06-24 | 2006-01-05 | Novartis Vaccines And Diagnostics Inc. | 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 |
| EP2129665A1 (en) * | 2007-04-05 | 2009-12-09 | CV Therapeutics Inc. | Quinazolinone derivatives as aldh-2 inhibitors |
| AU2008323953A1 (en) * | 2007-11-06 | 2009-05-14 | Gilead Palo Alto, Inc. | ALDH-2 inhibitors in the treatment of psychiatric disorders |
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- 2007-07-27 JP JP2009522029A patent/JP2009544742A/ja not_active Withdrawn
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- 2007-07-27 KR KR1020087029279A patent/KR20090033417A/ko not_active Withdrawn
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- 2008-11-27 MA MA31422A patent/MA30434B1/fr unknown
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