JP2009538335A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2009538335A5 JP2009538335A5 JP2009512259A JP2009512259A JP2009538335A5 JP 2009538335 A5 JP2009538335 A5 JP 2009538335A5 JP 2009512259 A JP2009512259 A JP 2009512259A JP 2009512259 A JP2009512259 A JP 2009512259A JP 2009538335 A5 JP2009538335 A5 JP 2009538335A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- alkyl
- isopropyl
- phenyl
- ylmethoxy
- 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.)
- Granted
Links
- 239000001257 hydrogen Substances 0.000 claims 34
- 229910052739 hydrogen Inorganic materials 0.000 claims 34
- 150000002431 hydrogen Chemical class 0.000 claims 25
- -1 C 1 -C 6 alkoxy Chemical group 0.000 claims 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 14
- 229910052799 carbon Inorganic materials 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 8
- 125000001475 halogen functional group Chemical group 0.000 claims 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 7
- 229910052801 chlorine Inorganic materials 0.000 claims 7
- 239000000460 chlorine Substances 0.000 claims 7
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 5
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 5
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 5
- 125000001041 indolyl group Chemical group 0.000 claims 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 5
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 4
- 229910052731 fluorine Inorganic materials 0.000 claims 4
- 239000011737 fluorine Substances 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 3
- 125000002541 furyl group Chemical group 0.000 claims 3
- 125000001624 naphthyl group Chemical group 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000000335 thiazolyl group Chemical group 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 239000005711 Benzoic acid Substances 0.000 claims 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical group CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 2
- 125000006833 (C1-C5) alkylene group Chemical group 0.000 claims 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 1
- GGNHFTLUMHDWKB-UHFFFAOYSA-N 1-methyl-6-[2-methyl-4-[[4-propan-2-yl-2-[2-(trifluoromethoxy)phenyl]pyrazol-3-yl]methoxy]phenyl]indole-3-carboxylic acid Chemical compound C=1C=C(C=2C=C3N(C)C=C(C3=CC=2)C(O)=O)C(C)=CC=1OCC1=C(C(C)C)C=NN1C1=CC=CC=C1OC(F)(F)F GGNHFTLUMHDWKB-UHFFFAOYSA-N 0.000 claims 1
- RLJHXZZDXOVPKO-UHFFFAOYSA-N 2-(butanoylamino)-4-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]benzoic acid Chemical compound C1=C(C(O)=O)C(NC(=O)CCC)=CC(CN(C)C=2C(=CC(OCC=3N(N=CC=3C(C)C)C=3C(=CC=CC=3Cl)Cl)=CC=2)C)=C1 RLJHXZZDXOVPKO-UHFFFAOYSA-N 0.000 claims 1
- ACXZZSVJTYLZNP-UHFFFAOYSA-N 2-butoxy-4-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]benzoic acid Chemical compound C1=C(C(O)=O)C(OCCCC)=CC(CN(C)C=2C(=CC(OCC=3N(N=CC=3C(C)C)C=3C(=CC=CC=3Cl)Cl)=CC=2)C)=C1 ACXZZSVJTYLZNP-UHFFFAOYSA-N 0.000 claims 1
- FZXSJMZVSAPXFE-UHFFFAOYSA-N 2-butoxy-5-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]benzoic acid Chemical compound C1=C(C(O)=O)C(OCCCC)=CC=C1CN(C)C(C(=C1)C)=CC=C1OCC1=C(C(C)C)C=NN1C1=C(Cl)C=CC=C1Cl FZXSJMZVSAPXFE-UHFFFAOYSA-N 0.000 claims 1
- HUMDEMOEWLRNNM-UHFFFAOYSA-N 2-methoxy-5-[[methyl-[2-methyl-6-[[4-propan-2-yl-2-[2-(trifluoromethoxy)phenyl]pyrazol-3-yl]methoxy]pyridin-3-yl]amino]methyl]benzoic acid Chemical compound C1=C(C(O)=O)C(OC)=CC=C1CN(C)C(C(=N1)C)=CC=C1OCC1=C(C(C)C)C=NN1C1=CC=CC=C1OC(F)(F)F HUMDEMOEWLRNNM-UHFFFAOYSA-N 0.000 claims 1
- ZCGIYEVATNPATF-UHFFFAOYSA-N 2-methyl-4-[[methyl-[2-methyl-6-[[4-propan-2-yl-2-[2-(trifluoromethoxy)phenyl]pyrazol-3-yl]methoxy]pyridin-3-yl]amino]methyl]benzoic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2)OC(F)(F)F)C=1COC(N=C1C)=CC=C1N(C)CC1=CC=C(C(O)=O)C(C)=C1 ZCGIYEVATNPATF-UHFFFAOYSA-N 0.000 claims 1
- SZUCNHMTJUGQAM-UHFFFAOYSA-N 3-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]-4-fluorobenzoic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2Cl)Cl)C=1COC(C=C1C)=CC=C1N(C)CC1=CC(C(O)=O)=CC=C1F SZUCNHMTJUGQAM-UHFFFAOYSA-N 0.000 claims 1
- JDMOVNWTUBRGJG-UHFFFAOYSA-N 3-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1CN(C)C(C(=C1)C)=CC=C1OCC1=C(C(C)C)C=NN1C1=C(Cl)C=CC=C1Cl JDMOVNWTUBRGJG-UHFFFAOYSA-N 0.000 claims 1
- LFMFHOSIFXYMRP-UHFFFAOYSA-N 3-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]-5-(trifluoromethyl)benzoic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2Cl)Cl)C=1COC(C=C1C)=CC=C1N(C)CC1=CC(C(O)=O)=CC(C(F)(F)F)=C1 LFMFHOSIFXYMRP-UHFFFAOYSA-N 0.000 claims 1
- QYBBADGECQOJHZ-UHFFFAOYSA-N 3-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]-5-methylbenzoic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2Cl)Cl)C=1COC(C=C1C)=CC=C1N(C)CC1=CC(C)=CC(C(O)=O)=C1 QYBBADGECQOJHZ-UHFFFAOYSA-N 0.000 claims 1
- JOPUCUPZVDBNPA-UHFFFAOYSA-N 3-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]benzoic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2Cl)Cl)C=1COC(C=C1C)=CC=C1N(C)CC1=CC=CC(C(O)=O)=C1 JOPUCUPZVDBNPA-UHFFFAOYSA-N 0.000 claims 1
- JDJSBOVIXJVINF-UHFFFAOYSA-N 3-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n-ethyl-2-methylanilino]methyl]benzoic acid Chemical compound C=1C=C(OCC=2N(N=CC=2C(C)C)C=2C(=CC=CC=2Cl)Cl)C=C(C)C=1N(CC)CC1=CC=CC(C(O)=O)=C1 JDJSBOVIXJVINF-UHFFFAOYSA-N 0.000 claims 1
- PNNSHXNLGFOCAJ-UHFFFAOYSA-N 3-[[[4-[[4-cyclopropyl-2-(2,6-dichlorophenyl)pyrazol-3-yl]methoxy]phenyl]methylamino]methyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(CNCC=2C=CC(OCC=3N(N=CC=3C3CC3)C=3C(=CC=CC=3Cl)Cl)=CC=2)=C1 PNNSHXNLGFOCAJ-UHFFFAOYSA-N 0.000 claims 1
- VYQZBAPNWMTQLG-UHFFFAOYSA-N 3-[[methyl-[2-methyl-6-[[4-propan-2-yl-2-[2-(trifluoromethoxy)phenyl]pyrazol-3-yl]methoxy]pyridin-3-yl]amino]methyl]benzoic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2)OC(F)(F)F)C=1COC(N=C1C)=CC=C1N(C)CC1=CC=CC(C(O)=O)=C1 VYQZBAPNWMTQLG-UHFFFAOYSA-N 0.000 claims 1
- NFEWMKBZBHGQJD-UHFFFAOYSA-N 3-[[n,2-dimethyl-4-[[4-propan-2-yl-2-[2-(trifluoromethoxy)phenyl]pyrazol-3-yl]methoxy]anilino]methyl]benzoic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2)OC(F)(F)F)C=1COC(C=C1C)=CC=C1N(C)CC1=CC=CC(C(O)=O)=C1 NFEWMKBZBHGQJD-UHFFFAOYSA-N 0.000 claims 1
- CENNTJAMJCFMBY-UHFFFAOYSA-N 3-butoxy-5-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]benzoic acid Chemical compound OC(=O)C1=CC(OCCCC)=CC(CN(C)C=2C(=CC(OCC=3N(N=CC=3C(C)C)C=3C(=CC=CC=3Cl)Cl)=CC=2)C)=C1 CENNTJAMJCFMBY-UHFFFAOYSA-N 0.000 claims 1
- PRXHPULVPUYSCR-UHFFFAOYSA-N 4-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]-2-(trifluoromethyl)benzoic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2Cl)Cl)C=1COC(C=C1C)=CC=C1N(C)CC1=CC=C(C(O)=O)C(C(F)(F)F)=C1 PRXHPULVPUYSCR-UHFFFAOYSA-N 0.000 claims 1
- PSEWBWUHJNKCHR-UHFFFAOYSA-N 4-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]-2-methoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OC)=CC(CN(C)C=2C(=CC(OCC=3N(N=CC=3C(C)C)C=3C(=CC=CC=3Cl)Cl)=CC=2)C)=C1 PSEWBWUHJNKCHR-UHFFFAOYSA-N 0.000 claims 1
- IWXHDMNTQMXGJI-UHFFFAOYSA-N 4-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]-2-methylbenzoic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2Cl)Cl)C=1COC(C=C1C)=CC=C1N(C)CC1=CC=C(C(O)=O)C(C)=C1 IWXHDMNTQMXGJI-UHFFFAOYSA-N 0.000 claims 1
- YYUPSWNBHVSIQR-UHFFFAOYSA-N 4-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]-2-pentylbenzoic acid Chemical compound C1=C(C(O)=O)C(CCCCC)=CC(CN(C)C=2C(=CC(OCC=3N(N=CC=3C(C)C)C=3C(=CC=CC=3Cl)Cl)=CC=2)C)=C1 YYUPSWNBHVSIQR-UHFFFAOYSA-N 0.000 claims 1
- NSVDMBZEFQUZEO-UHFFFAOYSA-N 4-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]-2-phenylmethoxybenzoic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2Cl)Cl)C=1COC(C=C1C)=CC=C1N(C)CC(C=1)=CC=C(C(O)=O)C=1OCC1=CC=CC=C1 NSVDMBZEFQUZEO-UHFFFAOYSA-N 0.000 claims 1
- QOTUZOQZTNNEIR-UHFFFAOYSA-N 4-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]-2-propan-2-yloxybenzoic acid Chemical compound C1=C(C(O)=O)C(OC(C)C)=CC(CN(C)C=2C(=CC(OCC=3N(N=CC=3C(C)C)C=3C(=CC=CC=3Cl)Cl)=CC=2)C)=C1 QOTUZOQZTNNEIR-UHFFFAOYSA-N 0.000 claims 1
- ZYPVLILUKZRKCD-UHFFFAOYSA-N 4-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]-3-hydroxybenzoic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2Cl)Cl)C=1COC(C=C1C)=CC=C1N(C)CC1=CC=C(C(O)=O)C=C1O ZYPVLILUKZRKCD-UHFFFAOYSA-N 0.000 claims 1
- IEEPTKVPJBRGTH-UHFFFAOYSA-N 4-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]benzoic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2Cl)Cl)C=1COC(C=C1C)=CC=C1N(C)CC1=CC=C(C(O)=O)C=C1 IEEPTKVPJBRGTH-UHFFFAOYSA-N 0.000 claims 1
- RHGRIDMWHLCVGZ-UHFFFAOYSA-N 4-[[methyl-[2-methyl-6-[[4-propan-2-yl-2-[2-(trifluoromethoxy)phenyl]pyrazol-3-yl]methoxy]pyridin-3-yl]amino]methyl]-2-pentylbenzoic acid Chemical compound C1=C(C(O)=O)C(CCCCC)=CC(CN(C)C=2C(=NC(OCC=3N(N=CC=3C(C)C)C=3C(=CC=CC=3)OC(F)(F)F)=CC=2)C)=C1 RHGRIDMWHLCVGZ-UHFFFAOYSA-N 0.000 claims 1
- RYGDOPNSOPUGDO-UHFFFAOYSA-N 4-[[methyl-[2-methyl-6-[[4-propan-2-yl-2-[2-(trifluoromethoxy)phenyl]pyrazol-3-yl]methoxy]pyridin-3-yl]amino]methyl]benzoic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2)OC(F)(F)F)C=1COC(N=C1C)=CC=C1N(C)CC1=CC=C(C(O)=O)C=C1 RYGDOPNSOPUGDO-UHFFFAOYSA-N 0.000 claims 1
- UXRMSUBAWLOIKL-UHFFFAOYSA-N 4-[[n,2-dimethyl-4-[[4-propan-2-yl-2-[2-(trifluoromethoxy)phenyl]pyrazol-3-yl]methoxy]anilino]methyl]-2-methylbenzoic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2)OC(F)(F)F)C=1COC(C=C1C)=CC=C1N(C)CC1=CC=C(C(O)=O)C(C)=C1 UXRMSUBAWLOIKL-UHFFFAOYSA-N 0.000 claims 1
- OMCYUGSEGWFIEN-UHFFFAOYSA-N 4-[[n,2-dimethyl-4-[[4-propan-2-yl-2-[2-(trifluoromethoxy)phenyl]pyrazol-3-yl]methoxy]anilino]methyl]benzoic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2)OC(F)(F)F)C=1COC(C=C1C)=CC=C1N(C)CC1=CC=C(C(O)=O)C=C1 OMCYUGSEGWFIEN-UHFFFAOYSA-N 0.000 claims 1
- NEXRZLRNZNTMOZ-UHFFFAOYSA-N 4-methyl-2-[2-methyl-4-[[4-propan-2-yl-2-[2-(trifluoromethoxy)phenyl]pyrazol-3-yl]methoxy]phenyl]-1,3-thiazole-5-carboxylic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2)OC(F)(F)F)C=1COC(C=C1C)=CC=C1C1=NC(C)=C(C(O)=O)S1 NEXRZLRNZNTMOZ-UHFFFAOYSA-N 0.000 claims 1
- ZLSHXKXFGGKERO-UHFFFAOYSA-N 5-[2-methyl-4-[[4-propan-2-yl-2-[2-(trifluoromethoxy)phenyl]pyrazol-3-yl]methoxy]phenyl]thiophene-2-carboxylic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2)OC(F)(F)F)C=1COC(C=C1C)=CC=C1C1=CC=C(C(O)=O)S1 ZLSHXKXFGGKERO-UHFFFAOYSA-N 0.000 claims 1
- GECYOKBCGOQDRO-UHFFFAOYSA-N 5-[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-2-methylphenyl]thiophene-2-carboxylic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2Cl)Cl)C=1COC(C=C1C)=CC=C1C1=CC=C(C(O)=O)S1 GECYOKBCGOQDRO-UHFFFAOYSA-N 0.000 claims 1
- JZMNRJPITYPLOG-UHFFFAOYSA-N 5-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]-2-fluorobenzoic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2Cl)Cl)C=1COC(C=C1C)=CC=C1N(C)CC1=CC=C(F)C(C(O)=O)=C1 JZMNRJPITYPLOG-UHFFFAOYSA-N 0.000 claims 1
- MBCMEMRMRKGJNN-UHFFFAOYSA-N 6-[2-methyl-4-[[4-propan-2-yl-2-[2-(trifluoromethoxy)phenyl]pyrazol-3-yl]methoxy]phenyl]-1-benzothiophene-3-carboxylic acid Chemical compound C=1C=C(C=2C=C3SC=C(C3=CC=2)C(O)=O)C(C)=CC=1OCC1=C(C(C)C)C=NN1C1=CC=CC=C1OC(F)(F)F MBCMEMRMRKGJNN-UHFFFAOYSA-N 0.000 claims 1
- FGOZUGVILLCUKR-UHFFFAOYSA-N 6-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]pyridine-3-carboxylic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2Cl)Cl)C=1COC(C=C1C)=CC=C1N(C)CC1=CC=C(C(O)=O)C=N1 FGOZUGVILLCUKR-UHFFFAOYSA-N 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 0 C*1C=C(*)C([n]2nc(C)c(*)c2C(C)(*)OC(I=*2)=CC(C)(*)C=C2I[Al]*)=C(C)C=C1 Chemical compound C*1C=C(*)C([n]2nc(C)c(*)c2C(C)(*)OC(I=*2)=CC(C)(*)C=C2I[Al]*)=C(C)C=C1 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80292006P | 2006-05-24 | 2006-05-24 | |
| US60/802,920 | 2006-05-24 | ||
| US86999506P | 2006-12-14 | 2006-12-14 | |
| US60/869,995 | 2006-12-14 | ||
| PCT/US2007/069445 WO2007140183A1 (en) | 2006-05-24 | 2007-05-22 | Fxr agonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009538335A JP2009538335A (ja) | 2009-11-05 |
| JP2009538335A5 true JP2009538335A5 (enExample) | 2010-05-27 |
| JP5119241B2 JP5119241B2 (ja) | 2013-01-16 |
Family
ID=42827365
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009512259A Active JP5119241B2 (ja) | 2006-05-24 | 2007-05-22 | Ｆｘｒアゴニスト |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US7846960B2 (enExample) |
| EP (1) | EP2029547B1 (enExample) |
| JP (1) | JP5119241B2 (enExample) |
| CN (1) | CN101448791B (enExample) |
| AT (1) | ATE465996T1 (enExample) |
| AU (1) | AU2007267606A1 (enExample) |
| BR (1) | BRPI0712262A2 (enExample) |
| CA (1) | CA2651378C (enExample) |
| DK (1) | DK2029547T3 (enExample) |
| EA (1) | EA015632B9 (enExample) |
| MX (1) | MX2008014854A (enExample) |
| PL (1) | PL2029547T3 (enExample) |
| WO (1) | WO2007140183A1 (enExample) |
Families Citing this family (68)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ581127A (en) | 2007-05-25 | 2012-06-29 | Abbott Gmbh & Co Kg | Heterocyclic compounds as positive modulators of metabotropic glutamate receptor 2 (mglu2 receptor) |
| TW200906823A (en) * | 2007-07-16 | 2009-02-16 | Lilly Co Eli | Compounds and methods for modulating FXR |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| US8217064B2 (en) | 2007-12-20 | 2012-07-10 | Envivo Pharmaceuticals, Inc. | Tetrasubstituted benzenes |
| EP2128158A1 (en) | 2008-05-26 | 2009-12-02 | Phenex Pharmaceuticals AG | Heterocyclic cyclopropyl-substituted FXR binding compounds |
| JP2012506386A (ja) * | 2008-10-21 | 2012-03-15 | メタボレックス， インコーポレイテッド | アリールｇｐｒ１２０受容体アゴニストおよびその使用 |
| EP2289883A1 (en) | 2009-08-19 | 2011-03-02 | Phenex Pharmaceuticals AG | Novel FXR (NR1H4) binding and activity modulating compounds |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8252826B2 (en) | 2010-03-24 | 2012-08-28 | Hoffmann-La Roche Inc. | Cyclopentyl- and cycloheptylpyrazoles |
| EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| US8871758B2 (en) | 2011-03-08 | 2014-10-28 | Sanofi | Tetrasubstituted oxathiazine derivatives, method for producing them, their use as medicine and drug containing said derivatives and the use thereof |
| US8828994B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Di- and tri-substituted oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| US8710050B2 (en) | 2011-03-08 | 2014-04-29 | Sanofi | Di and tri- substituted oxathiazine derivatives, method for the production, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| EP2683704B1 (de) | 2011-03-08 | 2014-12-17 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2766349B1 (de) | 2011-03-08 | 2016-06-01 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2545964A1 (en) | 2011-07-13 | 2013-01-16 | Phenex Pharmaceuticals AG | Novel FXR (NR1H4) binding and activity modulating compounds |
| WO2013037482A1 (en) | 2011-09-15 | 2013-03-21 | Phenex Pharmaceuticals Ag | Farnesoid x receptor agonists for cancer treatment and prevention |
| US8889730B2 (en) | 2012-04-10 | 2014-11-18 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
| CA2905242C (en) | 2013-03-15 | 2016-11-29 | Pfizer Inc. | Indole compounds that activate ampk |
| JP6366721B2 (ja) | 2013-09-11 | 2018-08-01 | アンスティチュ ナショナル ドゥ ラ サンテ エ ドゥ ラ ルシェルシュ メディカル | Ｂ型肝炎ウイルス感染症を処置するための方法及び医薬組成物 |
| DK3065738T3 (en) | 2013-11-05 | 2018-06-06 | Novartis Ag | Compositions and Methods for Modulating Farnesoid X Receptors |
| EP3006939A1 (en) | 2014-10-06 | 2016-04-13 | Gilead Sciences, Inc. | Histidine-rich Glycoprotein as a marker for hepatic Farnesoid X receptor activation |
| US10208081B2 (en) | 2014-11-26 | 2019-02-19 | Enanta Pharmaceuticals, Inc. | Bile acid derivatives as FXR/TGR5 agonists and methods of use thereof |
| EP3034499A1 (en) | 2014-12-17 | 2016-06-22 | Gilead Sciences, Inc. | Novel FXR (NR1H4) modulating compounds |
| EP3034501A1 (en) | 2014-12-17 | 2016-06-22 | Gilead Sciences, Inc. | Hydroxy containing FXR (NR1H4) modulating compounds |
| AR103624A1 (es) | 2015-02-06 | 2017-05-24 | Intercept Pharmaceuticals Inc | Composiciones farmacéuticas para terapia de combinación |
| TWI698430B (zh) | 2015-02-13 | 2020-07-11 | 南北兄弟藥業投資有限公司 | 三環化合物及其在藥物中的應用 |
| SI3277286T1 (sl) | 2015-03-31 | 2021-09-30 | Enanta Pharmaceuticals, Inc. | Derivati žolčne kisline kot antagonisti FXR/TGR5 in metode za njihovo uporabo |
| CA2981507A1 (en) | 2015-04-07 | 2016-10-13 | Intercept Pharmaceuticals, Inc. | Pharmaceutical compositions for combination therapy |
| EP3288948B1 (en) * | 2015-04-30 | 2019-11-20 | Novartis AG | Fused tricyclic pyrazole derivatives useful for modulating farnesoid x receptors |
| TWI752421B (zh) | 2015-12-16 | 2022-01-11 | 日商日本曹達股份有限公司 | 芳基唑化合物及有害生物防除劑 |
| WO2017189663A1 (en) | 2016-04-26 | 2017-11-02 | Enanta Pharmaceuticals, Inc. | Isoxazole derivatives as fxr agonists and methods of use thereof |
| US10080742B2 (en) | 2016-04-26 | 2018-09-25 | Enanta Pharmaceuticals, Inc. | Isoxazole derivatives as FXR agonists and methods of use thereof |
| WO2017189652A1 (en) | 2016-04-26 | 2017-11-02 | Enanta Pharmaceuticals, Inc. | Isoxazole derivatives as fxr agonists and methods of use thereof |
| US10144729B2 (en) | 2016-05-18 | 2018-12-04 | Enanta Pharmaceuticals, Inc. | Isoxazole analogs as FXR agonists and methods of use thereof |
| US10149835B2 (en) | 2016-05-18 | 2018-12-11 | Elmore Patent Law Group, P.C. | Isoxazole derivatives as FXR agonists and methods of use thereof |
| US10138228B2 (en) | 2016-05-18 | 2018-11-27 | Enanta Pharmaceuticals, Inc. | Isoxazole derivatives as FXR agonists and methods of use therof |
| CA2968836C (en) | 2016-06-13 | 2025-09-02 | Gilead Sciences, Inc. | FXR MODULATING COMPOUNDS (NR1H4) |
| ES2921432T3 (es) | 2016-06-13 | 2022-08-25 | Gilead Sciences Inc | Derivados de azetidina como moduladores de FXR (NR1H4) |
| TW201808283A (zh) * | 2016-08-05 | 2018-03-16 | 廣東東陽光藥業有限公司 | 含氮三環化合物及其在藥物中的應用 |
| CN109689050A (zh) * | 2016-09-14 | 2019-04-26 | 诺华股份有限公司 | Fxr激动剂的新方案 |
| EP3523298A4 (en) | 2016-10-04 | 2020-06-24 | Enanta Pharmaceuticals, Inc. | ISOXAZOLANALOGA AS FXR AGONISTS AND METHOD FOR USE THEREOF |
| US10597391B2 (en) | 2016-10-26 | 2020-03-24 | Enanta Pharmaceuticals, Inc. | Urea-containing isoxazole derivatives as FXR agonists and methods of use thereof |
| AU2018223146B2 (en) | 2017-02-21 | 2023-12-21 | Genfit | Combination of a PPAR agonist with a FXR agonist |
| EP4424364B1 (en) | 2017-03-28 | 2026-01-21 | Gilead Sciences, Inc. | Combinations for use in the treatment of cirrhosis and liver fibrosis |
| EP3600293A1 (en) | 2017-03-30 | 2020-02-05 | Institut National de la Sante et de la Recherche Medicale (INSERM) | Methods and pharmaceutical compositions for reducing persistence and expression of episomal viruses |
| SI3612520T1 (sl) | 2017-04-12 | 2022-01-31 | Il Dong Pharmaceutical Co., Ltd. | Izoksazolni derivati kot agonisti nuklearnega receptorja in njihove uporabe |
| CN111630051B (zh) | 2017-11-01 | 2023-12-26 | 百时美施贵宝公司 | 作为法尼醇x受体调节剂的烯烃螺环化合物 |
| KR102731925B1 (ko) | 2017-11-01 | 2024-11-18 | 브리스톨-마이어스 스큅 컴퍼니 | 파르네소이드 x 수용체 조정제로서의 멀티시클릭 화합물 |
| KR102732404B1 (ko) | 2017-11-01 | 2024-11-19 | 브리스톨-마이어스 스큅 컴퍼니 | 파르네소이드 x 수용체 조정제로서의 알켄 화합물 |
| US10689391B2 (en) | 2017-12-12 | 2020-06-23 | Enanta Pharmaceuticals, Inc. | Isoxazole analogs as FXR agonists and methods of use thereof |
| CN110128432B (zh) * | 2018-02-02 | 2021-03-02 | 广东东阳光药业有限公司 | 含氮三环化合物及其在药物中的应用 |
| CN108299405A (zh) * | 2018-02-12 | 2018-07-20 | 李化绪 | 3-对n,n二乙基氨基苯基亚氨基类化合物及其在高脂血症药物中的应用 |
| WO2019160813A1 (en) | 2018-02-14 | 2019-08-22 | Enanta Pharmaceuticals, Inc. | Isoxazole derivatives as fxr agonists and methods of use thereof |
| CA3104465A1 (en) | 2018-06-18 | 2019-12-26 | Epigen Biosciences, Inc. | Heterocyclic compounds useful in the treatment of disease |
| PE20211907A1 (es) | 2019-01-15 | 2021-09-28 | Gilead Sciences Inc | Compuestos moduladores de fxr (nr1h4) |
| KR102725082B1 (ko) | 2019-02-19 | 2024-11-04 | 길리애드 사이언시즈, 인코포레이티드 | Fxr 효능제의 고체 형태 |
| US11555032B2 (en) | 2019-05-13 | 2023-01-17 | Enanta Pharmaceuticals, Inc. | Isoxazole derivatives as FXR agonists and methods of use thereof |
| EA202193334A1 (ru) | 2019-05-30 | 2022-03-14 | Интерсепт Фармасьютикалз, Инк. | Фармацевтические композиции, содержащие агонист fxr и фибрат, для применения при лечении холестатического заболевания печени |
| AU2020312735A1 (en) | 2019-07-18 | 2021-12-16 | Enyo Pharma | Method for decreasing adverse-effects of interferon |
| WO2021108974A1 (en) | 2019-12-03 | 2021-06-10 | Gannex Pharma Co., Ltd | Compounds for modulating activity of fxr and uses thereof |
| CN110878052B (zh) * | 2019-12-11 | 2021-05-07 | 山东大学 | 一种含有fxr激动剂的化合物及其制备方法和应用 |
| WO2021122645A1 (en) | 2019-12-20 | 2021-06-24 | Syngenta Crop Protection Ag | Pesticidally active azole-amide compounds |
| US20230060715A1 (en) | 2020-01-15 | 2023-03-02 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Use of fxr agonists for treating an infection by hepatitis d virus |
| US20240100125A1 (en) | 2021-01-14 | 2024-03-28 | Enyo Pharma | Synergistic effect of a fxr agonist and ifn for the treatment of hbv infection |
| JP2024517181A (ja) | 2021-04-28 | 2024-04-19 | ウエヌイグレックオ・ファーマ | 組合せ治療としてｆｘｒアゴニストを使用するｔｌｒ３アゴニストの効果の強い増強 |
| JP7760117B2 (ja) * | 2021-08-23 | 2025-10-27 | 大学共同利用機関法人情報・システム研究機構 | オーキシンデグロンシステムのキット、及びその使用 |
| CN119462450A (zh) * | 2024-12-02 | 2025-02-18 | 西安近代化学研究所 | 一种双三氟甲基硫醚的制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07138258A (ja) * | 1993-11-16 | 1995-05-30 | Taiho Yakuhin Kogyo Kk | チアゾリジンジオン誘導体又はその塩 |
| ATE381542T1 (de) | 2001-08-13 | 2008-01-15 | Phenex Pharmaceuticals Ag | Nr1h4-kern-rezeptor-bindende verbindungen |
| EP1562915A1 (en) * | 2002-11-22 | 2005-08-17 | SmithKline Beecham Corporation | Farnesoid x receptor agonists |
| US7507832B2 (en) | 2003-12-22 | 2009-03-24 | Eli Lilly And Company | Triazole PPAR modulators |
-
2007
- 2007-05-22 EA EA200870570A patent/EA015632B9/ru not_active IP Right Cessation
- 2007-05-22 WO PCT/US2007/069445 patent/WO2007140183A1/en not_active Ceased
- 2007-05-22 BR BRPI0712262-4A patent/BRPI0712262A2/pt not_active IP Right Cessation
- 2007-05-22 MX MX2008014854A patent/MX2008014854A/es active IP Right Grant
- 2007-05-22 EP EP07797648A patent/EP2029547B1/en active Active
- 2007-05-22 CA CA2651378A patent/CA2651378C/en not_active Expired - Fee Related
- 2007-05-22 PL PL07797648T patent/PL2029547T3/pl unknown
- 2007-05-22 DK DK07797648.8T patent/DK2029547T3/da active
- 2007-05-22 JP JP2009512259A patent/JP5119241B2/ja active Active
- 2007-05-22 AT AT07797648T patent/ATE465996T1/de active
- 2007-05-22 AU AU2007267606A patent/AU2007267606A1/en not_active Abandoned
- 2007-05-22 US US12/296,534 patent/US7846960B2/en active Active
- 2007-05-22 CN CN2007800182169A patent/CN101448791B/zh not_active Expired - Fee Related