JP2009538335A5 - - Google Patents
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- 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
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- 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
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| EP2683699B1 (de) | 2011-03-08 | 2015-06-24 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| 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 |
| WO2012120056A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Tetrasubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
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| 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 |
| JP2006515838A (ja) * | 2002-11-22 | 2006-06-08 | スミスクライン ビーチャム コーポレーション | ファルネソイドｘ受容体アゴニスト |
| CA2549385A1 (en) | 2003-12-22 | 2005-07-21 | Eli Lilly And Company | Triazole, oxadiazole and thiadiazole derivative as ppar modulators for the treatment of diabetes |
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