JP2012506852A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2012506852A5 JP2012506852A5 JP2011532728A JP2011532728A JP2012506852A5 JP 2012506852 A5 JP2012506852 A5 JP 2012506852A5 JP 2011532728 A JP2011532728 A JP 2011532728A JP 2011532728 A JP2011532728 A JP 2011532728A JP 2012506852 A5 JP2012506852 A5 JP 2012506852A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- hydroxy
- acrylamide
- methoxy
- phenoxymethyl
- 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
- 150000001875 compounds Chemical class 0.000 claims 46
- 150000003839 salts Chemical class 0.000 claims 14
- 239000000651 prodrug Substances 0.000 claims 9
- 229940002612 prodrug Drugs 0.000 claims 9
- 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 8
- 239000000203 mixture Substances 0.000 claims 8
- -1 (3-Hydroxy-4-methoxy-phenyl) -N- [2- (2-methoxy-phenoxymethyl) -phenyl] -acrylamide Chemical compound 0.000 claims 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000001188 haloalkyl group Chemical group 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 230000003213 activating effect Effects 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 150000002431 hydrogen Chemical group 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000006239 protecting group Chemical group 0.000 claims 3
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 108010067028 Mitochondrial Permeability Transition Pore Proteins 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 229940059260 amidate Drugs 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- NPUKDXXFDDZOKR-LLVKDONJSA-N etomidate Chemical compound CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1 NPUKDXXFDDZOKR-LLVKDONJSA-N 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 208000028867 ischemia Diseases 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 230000000451 tissue damage Effects 0.000 claims 2
- 231100000827 tissue damage Toxicity 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- IPVASDRGUMHSRS-JYFOCSDGSA-N (E)-3-(3-hydroxyphenyl)-N-[4-[[4-[[(E)-3-(3-hydroxyphenyl)prop-2-enoyl]amino]phenyl]methyl]phenyl]prop-2-enamide Chemical compound OC=1C=C(C=CC=1)/C=C/C(=O)NC1=CC=C(C=C1)CC1=CC=C(C=C1)NC(\C=C\C1=CC(=CC=C1)O)=O IPVASDRGUMHSRS-JYFOCSDGSA-N 0.000 claims 1
- WBCOAFXNJNQWPX-PKNBQFBNSA-N (e)-3-(2,4-difluoro-3-hydroxyphenyl)-n-[2-[(3-piperidin-4-yloxyphenoxy)methyl]phenyl]prop-2-enamide Chemical compound OC1=C(F)C=CC(\C=C\C(=O)NC=2C(=CC=CC=2)COC=2C=C(OC3CCNCC3)C=CC=2)=C1F WBCOAFXNJNQWPX-PKNBQFBNSA-N 0.000 claims 1
- BUHGMAHKOMAYPJ-WUXMJOGZSA-N (e)-3-(2,4-difluoro-3-hydroxyphenyl)-n-[2-[(4-piperidin-4-yloxyphenoxy)methyl]phenyl]prop-2-enamide Chemical compound OC1=C(F)C=CC(\C=C\C(=O)NC=2C(=CC=CC=2)COC=2C=CC(OC3CCNCC3)=CC=2)=C1F BUHGMAHKOMAYPJ-WUXMJOGZSA-N 0.000 claims 1
- PFUUTYZVDQQGHE-ZRDIBKRKSA-N (e)-3-(2,4-difluoro-3-hydroxyphenyl)-n-[2-[[3-(1-methylpiperidin-4-yl)oxyphenoxy]methyl]phenyl]prop-2-enamide Chemical compound C1CN(C)CCC1OC1=CC=CC(OCC=2C(=CC=CC=2)NC(=O)\C=C\C=2C(=C(O)C(F)=CC=2)F)=C1 PFUUTYZVDQQGHE-ZRDIBKRKSA-N 0.000 claims 1
- BKVUTTRMHKZBNO-SOFGYWHQSA-N (e)-3-(2-chloro-3-hydroxy-4-methoxyphenyl)-n-(3-chlorophenyl)prop-2-enamide Chemical compound ClC1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC(Cl)=C1 BKVUTTRMHKZBNO-SOFGYWHQSA-N 0.000 claims 1
- BEVLVQGMYOLUBM-ZRDIBKRKSA-N (e)-3-(2-chloro-3-hydroxy-4-methoxyphenyl)-n-[2-[(3-piperidin-4-yloxyphenoxy)methyl]phenyl]prop-2-enamide Chemical compound ClC1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1COC1=CC=CC(OC2CCNCC2)=C1 BEVLVQGMYOLUBM-ZRDIBKRKSA-N 0.000 claims 1
- NNWANVGOYJJNIQ-ACCUITESSA-N (e)-3-(2-chloro-3-hydroxy-4-methoxyphenyl)-n-[2-[[3-(1-methylpiperidin-4-yl)oxyphenoxy]methyl]phenyl]prop-2-enamide Chemical compound ClC1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1COC1=CC=CC(OC2CCN(C)CC2)=C1 NNWANVGOYJJNIQ-ACCUITESSA-N 0.000 claims 1
- WCPZIHWJCKHVTG-VRTOBVRTSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-(1-methylbenzimidazol-2-yl)prop-2-enamide;hydrochloride Chemical compound Cl.C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=NC2=CC=CC=C2N1C WCPZIHWJCKHVTG-VRTOBVRTSA-N 0.000 claims 1
- LMWCBZYUBCCLGC-BXTVWIJMSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-(1-methylbenzimidazol-4-yl)prop-2-enamide;hydrochloride Chemical compound Cl.C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC2=C1N=CN2C LMWCBZYUBCCLGC-BXTVWIJMSA-N 0.000 claims 1
- AYPVBVXFHUNKDL-VQHVLOKHSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-(1-methylbenzotriazol-4-yl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC2=C1N=NN2C AYPVBVXFHUNKDL-VQHVLOKHSA-N 0.000 claims 1
- WXJYOKWPWWVYCW-VQHVLOKHSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-(1-methylindazol-4-yl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC2=C1C=NN2C WXJYOKWPWWVYCW-VQHVLOKHSA-N 0.000 claims 1
- JQEIVHPCOBHHKS-VQHVLOKHSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-(1-methylindol-4-yl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC2=C1C=CN2C JQEIVHPCOBHHKS-VQHVLOKHSA-N 0.000 claims 1
- HILQKBNRBWLIRU-VQHVLOKHSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-(2-methylindazol-7-yl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC2=CN(C)N=C12 HILQKBNRBWLIRU-VQHVLOKHSA-N 0.000 claims 1
- RGYGUMHSSDDNRA-WYMLVPIESA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-(2-phenylmethoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1OCC1=CC=CC=C1 RGYGUMHSSDDNRA-WYMLVPIESA-N 0.000 claims 1
- LPFBRHTWIWHUAD-SOFGYWHQSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-(3-iodophenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC(I)=C1 LPFBRHTWIWHUAD-SOFGYWHQSA-N 0.000 claims 1
- UMSNSJVTQIATDY-VQHVLOKHSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-(3-methoxyphenyl)prop-2-enamide Chemical compound COC1=CC=CC(NC(=O)\C=C\C=2C=C(O)C(OC)=CC=2)=C1 UMSNSJVTQIATDY-VQHVLOKHSA-N 0.000 claims 1
- VMPHIIJUTCREKJ-ACCUITESSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-(3-phenoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC(OC=2C=CC=CC=2)=C1 VMPHIIJUTCREKJ-ACCUITESSA-N 0.000 claims 1
- LIXJNYWAFUWMPI-ACCUITESSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-(3-phenylmethoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC(OCC=2C=CC=CC=2)=C1 LIXJNYWAFUWMPI-ACCUITESSA-N 0.000 claims 1
- YWKQTYSWIPWPOA-CSKARUKUSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-(3-propan-2-yloxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC(OC(C)C)=C1 YWKQTYSWIPWPOA-CSKARUKUSA-N 0.000 claims 1
- VBFVKRXOVOTHKC-SOFGYWHQSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-(3-pyridin-4-yloxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC(OC=2C=CN=CC=2)=C1 VBFVKRXOVOTHKC-SOFGYWHQSA-N 0.000 claims 1
- GQCJSHITDRNBGP-GQCTYLIASA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-(4-methoxypyrimidin-2-yl)prop-2-enamide Chemical compound COC1=CC=NC(NC(=O)\C=C\C=2C=C(O)C(OC)=CC=2)=N1 GQCJSHITDRNBGP-GQCTYLIASA-N 0.000 claims 1
- XNIDIIPKCNQFTM-RIYZIHGNSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-(4-phenylmethoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC(C=C1)=CC=C1OCC1=CC=CC=C1 XNIDIIPKCNQFTM-RIYZIHGNSA-N 0.000 claims 1
- WHYDQGXVXKCWPB-VQHVLOKHSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[1-[(1-methylimidazol-4-yl)methyl]indol-7-yl]prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC2=C1N(CC=1N=CN(C)C=1)C=C2 WHYDQGXVXKCWPB-VQHVLOKHSA-N 0.000 claims 1
- GMLMEGHAGMYWIV-VQHVLOKHSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[1-[(1-methylpyrazol-3-yl)methyl]indol-7-yl]prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC2=C1N(CC1=NN(C)C=C1)C=C2 GMLMEGHAGMYWIV-VQHVLOKHSA-N 0.000 claims 1
- MCVGCMNXBOVNPI-VQHVLOKHSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[1-[(3-methylimidazol-4-yl)methyl]indol-7-yl]prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC2=C1N(CC=1N(C=NC=1)C)C=C2 MCVGCMNXBOVNPI-VQHVLOKHSA-N 0.000 claims 1
- LNGQQLCMEVHLOV-XYOKQWHBSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[1-[(4-imidazol-1-ylphenyl)methyl]indol-7-yl]prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC2=C1N(CC=1C=CC(=CC=1)N1C=NC=C1)C=C2 LNGQQLCMEVHLOV-XYOKQWHBSA-N 0.000 claims 1
- ZVLFWDXJEDJZBC-ZRDIBKRKSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[1-[[3-(1-methylpiperidin-4-yl)oxyphenyl]methyl]indol-7-yl]prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC2=C1N(CC=1C=C(OC3CCN(C)CC3)C=CC=1)C=C2 ZVLFWDXJEDJZBC-ZRDIBKRKSA-N 0.000 claims 1
- DETDUUBLHIYFSU-WYMLVPIESA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[2-(2-phenylethoxy)phenyl]prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1OCCC1=CC=CC=C1 DETDUUBLHIYFSU-WYMLVPIESA-N 0.000 claims 1
- REIZVRJZMZPVIN-CSKARUKUSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[2-(methoxymethyl)phenyl]prop-2-enamide Chemical compound COCC1=CC=CC=C1NC(=O)\C=C\C1=CC=C(OC)C(O)=C1 REIZVRJZMZPVIN-CSKARUKUSA-N 0.000 claims 1
- WUJLMDGXFRGNBN-WYMLVPIESA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[2-(phenoxymethyl)phenyl]prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1COC1=CC=CC=C1 WUJLMDGXFRGNBN-WYMLVPIESA-N 0.000 claims 1
- PAHRGWXUKMTABU-BXTVWIJMSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[2-(pyridin-4-ylmethoxy)phenyl]prop-2-enamide;hydrochloride Chemical compound Cl.C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1OCC1=CC=NC=C1 PAHRGWXUKMTABU-BXTVWIJMSA-N 0.000 claims 1
- HIHFQJDKBDALBZ-BXTVWIJMSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[2-(pyridin-4-yloxymethyl)phenyl]prop-2-enamide;hydrochloride Chemical compound Cl.C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1COC1=CC=NC=C1 HIHFQJDKBDALBZ-BXTVWIJMSA-N 0.000 claims 1
- SPEMROBVFGSMHV-CSKARUKUSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[2-[(2-methylpyrazol-3-yl)oxymethyl]phenyl]prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1COC1=CC=NN1C SPEMROBVFGSMHV-CSKARUKUSA-N 0.000 claims 1
- GLHCBFXWUFOAIR-ACCUITESSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[2-[(3-methoxyphenoxy)methyl]phenyl]prop-2-enamide Chemical compound COC1=CC=CC(OCC=2C(=CC=CC=2)NC(=O)\C=C\C=2C=C(O)C(OC)=CC=2)=C1 GLHCBFXWUFOAIR-ACCUITESSA-N 0.000 claims 1
- SWICYRINRGYKIO-ZRDIBKRKSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[2-[(3-piperazin-1-ylphenoxy)methyl]phenyl]prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1COC1=CC=CC(N2CCNCC2)=C1 SWICYRINRGYKIO-ZRDIBKRKSA-N 0.000 claims 1
- YYNLBBPSGFTORK-ZRDIBKRKSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[2-[(3-piperidin-4-yloxyphenoxy)methyl]phenyl]prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1COC1=CC=CC(OC2CCNCC2)=C1 YYNLBBPSGFTORK-ZRDIBKRKSA-N 0.000 claims 1
- SAKLGWAFVKRZNN-NTUHNPAUSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[2-[(4-imidazol-1-ylphenoxy)methyl]phenyl]prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1COC1=CC=C(N2C=NC=C2)C=C1 SAKLGWAFVKRZNN-NTUHNPAUSA-N 0.000 claims 1
- FHQALPWIDOXNML-RIYZIHGNSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[2-[(4-methoxyphenoxy)methyl]phenyl]prop-2-enamide Chemical compound C1=CC(OC)=CC=C1OCC1=CC=CC=C1NC(=O)\C=C\C1=CC=C(OC)C(O)=C1 FHQALPWIDOXNML-RIYZIHGNSA-N 0.000 claims 1
- PJEIQEITFBMYRR-FTPOTTDRSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[2-[(4-piperidin-4-yloxyphenoxy)methyl]phenyl]prop-2-enamide;hydrochloride Chemical compound Cl.C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1COC(C=C1)=CC=C1OC1CCNCC1 PJEIQEITFBMYRR-FTPOTTDRSA-N 0.000 claims 1
- XUVPZPDGRZPLNR-WYMLVPIESA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[2-[[2-(1-methylpiperidin-4-yl)oxyphenoxy]methyl]phenyl]prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1COC1=CC=CC=C1OC1CCN(C)CC1 XUVPZPDGRZPLNR-WYMLVPIESA-N 0.000 claims 1
- XJRAASBJTJAOIH-WYMLVPIESA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[2-[[2-(4-methylpiperazin-1-yl)phenoxy]methyl]phenyl]prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1COC1=CC=CC=C1N1CCN(C)CC1 XJRAASBJTJAOIH-WYMLVPIESA-N 0.000 claims 1
- RQNUSJBRXHWSQE-ACCUITESSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[2-[[2-(trifluoromethyl)phenoxy]methyl]phenyl]prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1COC1=CC=CC=C1C(F)(F)F RQNUSJBRXHWSQE-ACCUITESSA-N 0.000 claims 1
- LNPPUWSHVAACMA-BNSHTTSQSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[2-[[3-(1-methylpiperidin-4-yl)oxyphenoxy]methyl]phenyl]prop-2-enamide;hydrochloride Chemical compound Cl.C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1COC1=CC=CC(OC2CCN(C)CC2)=C1 LNPPUWSHVAACMA-BNSHTTSQSA-N 0.000 claims 1
- PBESVOILTRCVKE-ACCUITESSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[2-[[3-(1-methylpiperidin-4-yl)phenoxy]methyl]phenyl]prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1COC1=CC=CC(C2CCN(C)CC2)=C1 PBESVOILTRCVKE-ACCUITESSA-N 0.000 claims 1
- CFEOXGWEJOHNFE-ACCUITESSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[2-[[3-(4-methylimidazol-1-yl)phenoxy]methyl]phenyl]prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1COC1=CC=CC(N2C=C(C)N=C2)=C1 CFEOXGWEJOHNFE-ACCUITESSA-N 0.000 claims 1
- IZKIDOWAKGHPEH-ZRDIBKRKSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[2-[[3-(trifluoromethyl)phenoxy]methyl]phenyl]prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1COC1=CC=CC(C(F)(F)F)=C1 IZKIDOWAKGHPEH-ZRDIBKRKSA-N 0.000 claims 1
- XAEVEZFYHNGOCX-XHIXCECLSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[2-[[4-(1-methylpiperidin-4-yl)oxyphenoxy]methyl]phenyl]prop-2-enamide;hydrochloride Chemical compound Cl.C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1COC(C=C1)=CC=C1OC1CCN(C)CC1 XAEVEZFYHNGOCX-XHIXCECLSA-N 0.000 claims 1
- OLOBCAYGFJCTBZ-RIYZIHGNSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[2-[[4-(1-methylpiperidin-4-yl)phenoxy]methyl]phenyl]prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1COC1=CC=C(C2CCN(C)CC2)C=C1 OLOBCAYGFJCTBZ-RIYZIHGNSA-N 0.000 claims 1
- RUVQJKZGWPLVDE-XHIXCECLSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[2-[[4-(4-methylimidazol-1-yl)phenoxy]methyl]phenyl]prop-2-enamide;hydrochloride Chemical compound Cl.C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1COC1=CC=C(N2C=C(C)N=C2)C=C1 RUVQJKZGWPLVDE-XHIXCECLSA-N 0.000 claims 1
- FKRYGSXGEAVPOS-XHIXCECLSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[2-[[4-(4-methylpiperazin-1-yl)phenoxy]methyl]phenyl]prop-2-enamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1COC1=CC=C(N2CCN(C)CC2)C=C1 FKRYGSXGEAVPOS-XHIXCECLSA-N 0.000 claims 1
- ITBAMRIAZDDJJF-KJEVSKRMSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[2-[[4-(morpholin-4-ylmethyl)phenoxy]methyl]phenyl]prop-2-enamide;hydrochloride Chemical compound Cl.C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1COC(C=C1)=CC=C1CN1CCOCC1 ITBAMRIAZDDJJF-KJEVSKRMSA-N 0.000 claims 1
- FHTDLIYRMXGUEO-CLNHMMGSSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[2-[[4-(piperidin-1-ylmethyl)phenoxy]methyl]phenyl]prop-2-enamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1COC(C=C1)=CC=C1CN1CCCCC1 FHTDLIYRMXGUEO-CLNHMMGSSA-N 0.000 claims 1
- RWQDJMMKFKDLAB-KRWCAOSLSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[2-[[4-(pyrrolidin-1-ylmethyl)phenoxy]methyl]phenyl]prop-2-enamide;hydrochloride Chemical compound Cl.C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1COC(C=C1)=CC=C1CN1CCCC1 RWQDJMMKFKDLAB-KRWCAOSLSA-N 0.000 claims 1
- JXUWLLPWZIWXFF-NTUHNPAUSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[2-[[4-(trifluoromethyl)phenoxy]methyl]phenyl]prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1COC1=CC=C(C(F)(F)F)C=C1 JXUWLLPWZIWXFF-NTUHNPAUSA-N 0.000 claims 1
- VPRAOQWMTGHQII-GXDHUFHOSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[2-[[4-[(1-methylpiperidin-4-yl)methyl]phenoxy]methyl]phenyl]prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1COC(C=C1)=CC=C1CC1CCN(C)CC1 VPRAOQWMTGHQII-GXDHUFHOSA-N 0.000 claims 1
- PZBNKJAWXQJJAK-GXDHUFHOSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[2-[[4-[(4-methylpiperazin-1-yl)methyl]phenoxy]methyl]phenyl]prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1COC(C=C1)=CC=C1CN1CCN(C)CC1 PZBNKJAWXQJJAK-GXDHUFHOSA-N 0.000 claims 1
- BMVPJPICBNAZMM-SOFGYWHQSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[3-(1,3-oxazol-5-yl)phenyl]prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC(C=2OC=NC=2)=C1 BMVPJPICBNAZMM-SOFGYWHQSA-N 0.000 claims 1
- IRQWOYDQSIXGNL-VQHVLOKHSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[3-(1-methylpiperidin-4-yl)oxyphenyl]prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC(OC2CCN(C)CC2)=C1 IRQWOYDQSIXGNL-VQHVLOKHSA-N 0.000 claims 1
- XSRPDHPWYIKETM-WVLIHFOGSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[3-(1h-imidazol-5-ylmethoxy)phenyl]prop-2-enamide;hydrochloride Chemical compound Cl.C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC(OCC=2N=CNC=2)=C1 XSRPDHPWYIKETM-WVLIHFOGSA-N 0.000 claims 1
- GOWXGFXCTUIFAQ-ACCUITESSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[3-(2-phenylethoxy)phenyl]prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC(OCCC=2C=CC=CC=2)=C1 GOWXGFXCTUIFAQ-ACCUITESSA-N 0.000 claims 1
- KSDGXYCNWVCBTQ-SOFGYWHQSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[3-(2h-tetrazol-5-ylmethoxy)phenyl]prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC(OCC=2NN=NN=2)=C1 KSDGXYCNWVCBTQ-SOFGYWHQSA-N 0.000 claims 1
- QNTUWADSMRNNDU-VQHVLOKHSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[3-(4-methylpiperazin-1-yl)phenyl]prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC(N2CCN(C)CC2)=C1 QNTUWADSMRNNDU-VQHVLOKHSA-N 0.000 claims 1
- ALLNPSJQYRMERY-PKNBQFBNSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[3-(pyridin-2-ylmethoxy)phenyl]prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC(OCC=2N=CC=CC=2)=C1 ALLNPSJQYRMERY-PKNBQFBNSA-N 0.000 claims 1
- KMWIEXGXRJUPMY-CSKARUKUSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[3-(pyridin-3-ylmethoxy)phenyl]prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC(OCC=2C=NC=CC=2)=C1 KMWIEXGXRJUPMY-CSKARUKUSA-N 0.000 claims 1
- YDPVWKNSJYUKKX-SOFGYWHQSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[3-(pyridin-4-ylmethoxy)phenyl]prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC(OCC=2C=CN=CC=2)=C1 YDPVWKNSJYUKKX-SOFGYWHQSA-N 0.000 claims 1
- IRZLTSQDMNQDCY-SOFGYWHQSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[3-(pyridin-4-ylmethylamino)phenyl]prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC(NCC=2C=CN=CC=2)=C1 IRZLTSQDMNQDCY-SOFGYWHQSA-N 0.000 claims 1
- JSRBCUSQNLEKTF-WVLIHFOGSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[3-(pyridin-4-ylmethylsulfanyl)phenyl]prop-2-enamide;hydrochloride Chemical compound Cl.C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC(SCC=2C=CN=CC=2)=C1 JSRBCUSQNLEKTF-WVLIHFOGSA-N 0.000 claims 1
- ZVKUYMFBLNGQNN-WVLIHFOGSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[3-(pyridin-4-yloxymethyl)phenyl]prop-2-enamide;hydrochloride Chemical compound Cl.C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC(COC=2C=CN=CC=2)=C1 ZVKUYMFBLNGQNN-WVLIHFOGSA-N 0.000 claims 1
- AIZJEMDAULQQJL-SOFGYWHQSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[3-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC(C(F)(F)F)=C1 AIZJEMDAULQQJL-SOFGYWHQSA-N 0.000 claims 1
- QRKHUWZEGBWRCR-VQHVLOKHSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[3-[(1-methylimidazol-2-yl)methoxy]phenyl]prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC(OCC=2N(C=CN=2)C)=C1 QRKHUWZEGBWRCR-VQHVLOKHSA-N 0.000 claims 1
- IOLAFEJFJNDSQO-PKNBQFBNSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[3-[(1-methylpiperidin-3-yl)methoxy]phenyl]prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC(OCC2CN(C)CCC2)=C1 IOLAFEJFJNDSQO-PKNBQFBNSA-N 0.000 claims 1
- VHXPVJDDKXELPW-VQHVLOKHSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[3-[(3-methylimidazol-4-yl)methoxy]phenyl]prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC(OCC=2N(C=NC=2)C)=C1 VHXPVJDDKXELPW-VQHVLOKHSA-N 0.000 claims 1
- RCPIIEJWFHBXAL-DHZHZOJOSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[3-[(5-methylfuran-2-yl)methoxy]phenyl]prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC(OCC=2OC(C)=CC=2)=C1 RCPIIEJWFHBXAL-DHZHZOJOSA-N 0.000 claims 1
- OVEARYPJKNLPFO-KJEVSKRMSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-[4-(4-methylpiperazin-1-yl)-2-(phenoxymethyl)phenyl]prop-2-enamide;hydrochloride Chemical compound Cl.C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=C(N2CCN(C)CC2)C=C1COC1=CC=CC=C1 OVEARYPJKNLPFO-KJEVSKRMSA-N 0.000 claims 1
- KREVXENGHMWDSK-ZRDIBKRKSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-n-naphthalen-1-ylprop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC2=CC=CC=C12 KREVXENGHMWDSK-ZRDIBKRKSA-N 0.000 claims 1
- LSKOSNBEWJCPGC-BUHFOSPRSA-N (e)-3-(3-hydroxyphenyl)-n-[2-(phenoxymethyl)phenyl]prop-2-enamide Chemical compound OC1=CC=CC(\C=C\C(=O)NC=2C(=CC=CC=2)COC=2C=CC=CC=2)=C1 LSKOSNBEWJCPGC-BUHFOSPRSA-N 0.000 claims 1
- JRWFUKFQMKBZPR-FNORWQNLSA-N (e)-3-(4-amino-3-hydroxyphenyl)-n-(3-chlorophenyl)prop-2-enamide Chemical compound C1=C(O)C(N)=CC=C1\C=C\C(=O)NC1=CC=CC(Cl)=C1 JRWFUKFQMKBZPR-FNORWQNLSA-N 0.000 claims 1
- DWRRPLVNAKWCMR-FNORWQNLSA-N (e)-3-(4-chloro-3-hydroxyphenyl)-n-(3-chlorophenyl)prop-2-enamide Chemical compound C1=C(Cl)C(O)=CC(\C=C\C(=O)NC=2C=C(Cl)C=CC=2)=C1 DWRRPLVNAKWCMR-FNORWQNLSA-N 0.000 claims 1
- PXJQMSZBZLDFSG-PKNBQFBNSA-N (e)-3-(4-chloro-3-hydroxyphenyl)-n-[2-[(3-piperidin-4-yloxyphenoxy)methyl]phenyl]prop-2-enamide Chemical compound C1=C(Cl)C(O)=CC(\C=C\C(=O)NC=2C(=CC=CC=2)COC=2C=C(OC3CCNCC3)C=CC=2)=C1 PXJQMSZBZLDFSG-PKNBQFBNSA-N 0.000 claims 1
- AEXNOYYOYOUNFF-PKNBQFBNSA-N (e)-3-(4-cyano-3-hydroxyphenyl)-n-[2-[(3-piperidin-4-yloxyphenoxy)methyl]phenyl]prop-2-enamide Chemical compound C1=C(C#N)C(O)=CC(\C=C\C(=O)NC=2C(=CC=CC=2)COC=2C=C(OC3CCNCC3)C=CC=2)=C1 AEXNOYYOYOUNFF-PKNBQFBNSA-N 0.000 claims 1
- QREYOCSQFKTAFK-ZRDIBKRKSA-N (e)-3-(4-cyano-3-hydroxyphenyl)-n-[2-[[3-(1-methylpiperidin-4-yl)oxyphenoxy]methyl]phenyl]prop-2-enamide Chemical compound C1CN(C)CCC1OC1=CC=CC(OCC=2C(=CC=CC=2)NC(=O)\C=C\C=2C=C(O)C(C#N)=CC=2)=C1 QREYOCSQFKTAFK-ZRDIBKRKSA-N 0.000 claims 1
- MSXASVYCAIQIDA-NTUHNPAUSA-N (e)-3-(4-cyano-3-hydroxyphenyl)-n-[2-[[4-(1-methylpiperidin-4-yl)oxyphenoxy]methyl]phenyl]prop-2-enamide Chemical compound C1CN(C)CCC1OC(C=C1)=CC=C1OCC1=CC=CC=C1NC(=O)\C=C\C1=CC=C(C#N)C(O)=C1 MSXASVYCAIQIDA-NTUHNPAUSA-N 0.000 claims 1
- KSKIGBGMPMGLEU-ACCUITESSA-N (e)-3-(4-fluoro-3-hydroxyphenyl)-n-(2-phenylmethoxyphenyl)prop-2-enamide Chemical compound C1=C(F)C(O)=CC(\C=C\C(=O)NC=2C(=CC=CC=2)OCC=2C=CC=CC=2)=C1 KSKIGBGMPMGLEU-ACCUITESSA-N 0.000 claims 1
- NLVSGTNEVLQYGJ-YRNVUSSQSA-N (e)-3-(4-fluoro-3-hydroxyphenyl)-n-[1-[(4-imidazol-1-ylphenyl)methyl]indol-7-yl]prop-2-enamide Chemical compound C1=C(F)C(O)=CC(\C=C\C(=O)NC=2C=3N(CC=4C=CC(=CC=4)N4C=NC=C4)C=CC=3C=CC=2)=C1 NLVSGTNEVLQYGJ-YRNVUSSQSA-N 0.000 claims 1
- CAWZFQQHSGYGDU-ACCUITESSA-N (e)-3-(4-fluoro-3-hydroxyphenyl)-n-[2-(phenoxymethyl)phenyl]prop-2-enamide Chemical compound C1=C(F)C(O)=CC(\C=C\C(=O)NC=2C(=CC=CC=2)COC=2C=CC=CC=2)=C1 CAWZFQQHSGYGDU-ACCUITESSA-N 0.000 claims 1
- INOQCULEIIHTLC-WUXMJOGZSA-N (e)-3-(4-fluoro-3-hydroxyphenyl)-n-[2-[(4-imidazol-1-ylphenoxy)methyl]phenyl]prop-2-enamide Chemical compound C1=C(F)C(O)=CC(\C=C\C(=O)NC=2C(=CC=CC=2)COC=2C=CC(=CC=2)N2C=NC=C2)=C1 INOQCULEIIHTLC-WUXMJOGZSA-N 0.000 claims 1
- QRTUOPQCMFKZJB-FTPOTTDRSA-N (e)-3-(4-fluoro-3-hydroxyphenyl)-n-[2-[[4-(1-methylpiperidin-4-yl)oxyphenoxy]methyl]phenyl]prop-2-enamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1CN(C)CCC1OC(C=C1)=CC=C1OCC1=CC=CC=C1NC(=O)\C=C\C1=CC=C(F)C(O)=C1 QRTUOPQCMFKZJB-FTPOTTDRSA-N 0.000 claims 1
- JUAHSUDLOVMRBS-GZOLSCHFSA-N (e)-3-(4-fluoro-3-hydroxyphenyl)-n-[3-(pyridin-4-ylmethoxy)phenyl]prop-2-enamide;hydrochloride Chemical compound Cl.C1=C(F)C(O)=CC(\C=C\C(=O)NC=2C=C(OCC=3C=CN=CC=3)C=CC=2)=C1 JUAHSUDLOVMRBS-GZOLSCHFSA-N 0.000 claims 1
- XISTYJKZNFWAHP-FNORWQNLSA-N (e)-3-(4-fluoro-3-hydroxyphenyl)-n-[3-(pyridin-4-ylmethylsulfanyl)phenyl]prop-2-enamide Chemical compound C1=C(F)C(O)=CC(\C=C\C(=O)NC=2C=C(SCC=3C=CN=CC=3)C=CC=2)=C1 XISTYJKZNFWAHP-FNORWQNLSA-N 0.000 claims 1
- BMCSPJSYPPZCJI-PKNBQFBNSA-N (e)-3-(4-fluoro-3-hydroxyphenyl)-n-naphthalen-1-ylprop-2-enamide Chemical compound C1=C(F)C(O)=CC(\C=C\C(=O)NC=2C3=CC=CC=C3C=CC=2)=C1 BMCSPJSYPPZCJI-PKNBQFBNSA-N 0.000 claims 1
- SAEIZUFGIALRFN-XVNBXDOJSA-N (e)-n-(1,3-benzodioxol-5-yl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=C(OCO2)C2=C1 SAEIZUFGIALRFN-XVNBXDOJSA-N 0.000 claims 1
- LCCYEABGYXFCIU-SOFGYWHQSA-N (e)-n-(1,3-benzoxazol-4-yl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC2=C1N=CO2 LCCYEABGYXFCIU-SOFGYWHQSA-N 0.000 claims 1
- YCIAKCDKUNUOSD-ACCUITESSA-N (e)-n-(1-benzylbenzimidazol-4-yl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC2=C1N=CN2CC1=CC=CC=C1 YCIAKCDKUNUOSD-ACCUITESSA-N 0.000 claims 1
- IJBSUDJLRSOOSR-BNSHTTSQSA-N (e)-n-(1-benzylindazol-4-yl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide;hydrochloride Chemical compound Cl.C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC2=C1C=NN2CC1=CC=CC=C1 IJBSUDJLRSOOSR-BNSHTTSQSA-N 0.000 claims 1
- JPUSPTLXNMDTDL-ACCUITESSA-N (e)-n-(1-benzylindazol-7-yl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC2=C1N(CC=1C=CC=CC=1)N=C2 JPUSPTLXNMDTDL-ACCUITESSA-N 0.000 claims 1
- BZZCBBRRAUINHS-ZRDIBKRKSA-N (e)-n-(1-benzylindazol-7-yl)-3-(4-fluoro-3-hydroxyphenyl)prop-2-enamide Chemical compound C1=C(F)C(O)=CC(\C=C\C(=O)NC=2C=3N(CC=4C=CC=CC=4)N=CC=3C=CC=2)=C1 BZZCBBRRAUINHS-ZRDIBKRKSA-N 0.000 claims 1
- OFNLDTMWBKCOFE-ACCUITESSA-N (e)-n-(1-benzylindol-4-yl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC2=C1C=CN2CC1=CC=CC=C1 OFNLDTMWBKCOFE-ACCUITESSA-N 0.000 claims 1
- PZGPJKKMLWTIME-ACCUITESSA-N (e)-n-(1-benzylindol-7-yl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC2=C1N(CC=1C=CC=CC=1)C=C2 PZGPJKKMLWTIME-ACCUITESSA-N 0.000 claims 1
- DYOKPQPPLYZRCT-ZRDIBKRKSA-N (e)-n-(1-benzylindol-7-yl)-3-(4-fluoro-3-hydroxyphenyl)prop-2-enamide Chemical compound C1=C(F)C(O)=CC(\C=C\C(=O)NC=2C=3N(CC=4C=CC=CC=4)C=CC=3C=CC=2)=C1 DYOKPQPPLYZRCT-ZRDIBKRKSA-N 0.000 claims 1
- KTULBNXSPCRURV-SOFGYWHQSA-N (e)-n-(2,3-dichlorophenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC(Cl)=C1Cl KTULBNXSPCRURV-SOFGYWHQSA-N 0.000 claims 1
- CWLAHZVVISHPRH-FNORWQNLSA-N (e)-n-(2,3-dichlorophenyl)-3-(4-fluoro-3-hydroxyphenyl)prop-2-enamide Chemical compound C1=C(F)C(O)=CC(\C=C\C(=O)NC=2C(=C(Cl)C=CC=2)Cl)=C1 CWLAHZVVISHPRH-FNORWQNLSA-N 0.000 claims 1
- PPVRRXUNDWOBFH-YRNVUSSQSA-N (e)-n-(2,3-dihydro-1h-inden-1-yl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1C2=CC=CC=C2CC1 PPVRRXUNDWOBFH-YRNVUSSQSA-N 0.000 claims 1
- MLJMLDPBRNYKAI-ACCUITESSA-N (e)-n-(2-benzylindazol-7-yl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC(C1=N2)=CC=CC1=CN2CC1=CC=CC=C1 MLJMLDPBRNYKAI-ACCUITESSA-N 0.000 claims 1
- PUJGCQRKRDSMNM-WYMLVPIESA-N (e)-n-(2-benzylsulfanylphenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1SCC1=CC=CC=C1 PUJGCQRKRDSMNM-WYMLVPIESA-N 0.000 claims 1
- SSMUZKGIQZHBOO-ACCUITESSA-N (e)-n-(2-chloro-3-phenylmethoxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC(OCC=2C=CC=CC=2)=C1Cl SSMUZKGIQZHBOO-ACCUITESSA-N 0.000 claims 1
- FQHHEOPVSMHPDJ-VQHVLOKHSA-N (e)-n-(2-chlorophenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1Cl FQHHEOPVSMHPDJ-VQHVLOKHSA-N 0.000 claims 1
- CPLDLWIDEOPNKU-HWKANZROSA-N (e)-n-(2-chloropyridin-4-yl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=NC(Cl)=C1 CPLDLWIDEOPNKU-HWKANZROSA-N 0.000 claims 1
- OSTVRNNGUODLSQ-XVNBXDOJSA-N (e)-n-(3,4-dichlorophenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=C(Cl)C(Cl)=C1 OSTVRNNGUODLSQ-XVNBXDOJSA-N 0.000 claims 1
- RJBCJFINDOBORW-HWKANZROSA-N (e)-n-(3,5-dichlorophenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC(Cl)=CC(Cl)=C1 RJBCJFINDOBORW-HWKANZROSA-N 0.000 claims 1
- VMQAKYLSLUZAPP-ACCUITESSA-N (e)-n-(3-benzylbenzimidazol-4-yl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC2=C1N(CC=1C=CC=CC=1)C=N2 VMQAKYLSLUZAPP-ACCUITESSA-N 0.000 claims 1
- CIOACCYKFZAHGL-ZRDIBKRKSA-N (e)-n-(3-benzylbenzimidazol-4-yl)-3-(4-fluoro-3-hydroxyphenyl)prop-2-enamide Chemical compound C1=C(F)C(O)=CC(\C=C\C(=O)NC=2C=3N(CC=4C=CC=CC=4)C=NC=3C=CC=2)=C1 CIOACCYKFZAHGL-ZRDIBKRKSA-N 0.000 claims 1
- WUVWGNGXMVXDMS-SOFGYWHQSA-N (e)-n-(3-bromophenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC(Br)=C1 WUVWGNGXMVXDMS-SOFGYWHQSA-N 0.000 claims 1
- DWBKZPONDCSVJB-FNORWQNLSA-N (e)-n-(3-bromophenyl)-3-(4-fluoro-3-hydroxyphenyl)prop-2-enamide Chemical compound C1=C(F)C(O)=CC(\C=C\C(=O)NC=2C=C(Br)C=CC=2)=C1 DWBKZPONDCSVJB-FNORWQNLSA-N 0.000 claims 1
- LOHSLYPYCRWSOI-VQHVLOKHSA-N (e)-n-(3-chloro-2-methoxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC(Cl)=C1OC LOHSLYPYCRWSOI-VQHVLOKHSA-N 0.000 claims 1
- ZRHCDGUXVFKZQC-ACCUITESSA-N (e)-n-(3-chloro-2-phenylmethoxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC(Cl)=C1OCC1=CC=CC=C1 ZRHCDGUXVFKZQC-ACCUITESSA-N 0.000 claims 1
- OZFHRNUPDHXJIG-XBXARRHUSA-N (e)-n-(3-chloro-4-methoxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=C(OC)C(Cl)=C1 OZFHRNUPDHXJIG-XBXARRHUSA-N 0.000 claims 1
- NWNDTGTYJFVXDK-VQHVLOKHSA-N (e)-n-(3-chloronaphthalen-1-yl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC(Cl)=CC2=CC=CC=C12 NWNDTGTYJFVXDK-VQHVLOKHSA-N 0.000 claims 1
- MCPRXSHVOVRGES-FNORWQNLSA-N (e)-n-(3-chlorophenyl)-3-(2,4-difluoro-3-hydroxyphenyl)prop-2-enamide Chemical compound OC1=C(F)C=CC(\C=C\C(=O)NC=2C=C(Cl)C=CC=2)=C1F MCPRXSHVOVRGES-FNORWQNLSA-N 0.000 claims 1
- UBNJOSSBOHRSMZ-SOFGYWHQSA-N (e)-n-(3-chlorophenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC(Cl)=C1 UBNJOSSBOHRSMZ-SOFGYWHQSA-N 0.000 claims 1
- MDORILUITRSFPJ-BQYQJAHWSA-N (e)-n-(3-chlorophenyl)-3-(3-hydroxy-4-methylphenyl)prop-2-enamide Chemical compound C1=C(O)C(C)=CC=C1\C=C\C(=O)NC1=CC=CC(Cl)=C1 MDORILUITRSFPJ-BQYQJAHWSA-N 0.000 claims 1
- DIEHDKJOLNIWGF-FNORWQNLSA-N (e)-n-(3-chlorophenyl)-3-(3-hydroxy-4-sulfamoylphenyl)prop-2-enamide Chemical compound C1=C(O)C(S(=O)(=O)N)=CC=C1\C=C\C(=O)NC1=CC=CC(Cl)=C1 DIEHDKJOLNIWGF-FNORWQNLSA-N 0.000 claims 1
- IZXYYBWPDVJZIX-BQYQJAHWSA-N (e)-n-(3-chlorophenyl)-3-(3-hydroxyphenyl)prop-2-enamide Chemical compound OC1=CC=CC(\C=C\C(=O)NC=2C=C(Cl)C=CC=2)=C1 IZXYYBWPDVJZIX-BQYQJAHWSA-N 0.000 claims 1
- ABDYPJXYJPNHSQ-FNORWQNLSA-N (e)-n-(3-chlorophenyl)-3-(4-cyano-3-hydroxyphenyl)prop-2-enamide Chemical compound C1=C(C#N)C(O)=CC(\C=C\C(=O)NC=2C=C(Cl)C=CC=2)=C1 ABDYPJXYJPNHSQ-FNORWQNLSA-N 0.000 claims 1
- FJCZKRFAPDGACF-FNORWQNLSA-N (e)-n-(3-chlorophenyl)-3-(4-fluoro-3-hydroxyphenyl)prop-2-enamide Chemical compound C1=C(F)C(O)=CC(\C=C\C(=O)NC=2C=C(Cl)C=CC=2)=C1 FJCZKRFAPDGACF-FNORWQNLSA-N 0.000 claims 1
- WMYDXOIUWDCDMY-SOFGYWHQSA-N (e)-n-(3-fluorophenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC(F)=C1 WMYDXOIUWDCDMY-SOFGYWHQSA-N 0.000 claims 1
- PYYVTCWJSIBOCF-YCRREMRBSA-N (e)-n-(4-chlorophenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=C(Cl)C=C1 PYYVTCWJSIBOCF-YCRREMRBSA-N 0.000 claims 1
- WOVOPDXGRDPAMO-UXBLZVDNSA-N (e)-n-(4-ethoxy-1-methylindazol-7-yl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=2N(C)N=CC=2C(OCC)=CC=C1NC(=O)\C=C\C1=CC=C(OC)C(O)=C1 WOVOPDXGRDPAMO-UXBLZVDNSA-N 0.000 claims 1
- CKTMDZISGSKHFQ-ZRDIBKRKSA-N (e)-n-[2-(cyclobutyloxymethyl)phenyl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1COC1CCC1 CKTMDZISGSKHFQ-ZRDIBKRKSA-N 0.000 claims 1
- KVNWAODWEOLZJM-ACCUITESSA-N (e)-n-[2-[(2-chlorophenoxy)methyl]phenyl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1COC1=CC=CC=C1Cl KVNWAODWEOLZJM-ACCUITESSA-N 0.000 claims 1
- PKMXZVFPEGZLOM-ACCUITESSA-N (e)-n-[2-[(2-fluorophenoxy)methyl]phenyl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1COC1=CC=CC=C1F PKMXZVFPEGZLOM-ACCUITESSA-N 0.000 claims 1
- ZNDCIGCIRKQKKK-ZRDIBKRKSA-N (e)-n-[2-[(3-chlorophenoxy)methyl]phenyl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1COC1=CC=CC(Cl)=C1 ZNDCIGCIRKQKKK-ZRDIBKRKSA-N 0.000 claims 1
- SFFKWDZELGYSNA-ZRDIBKRKSA-N (e)-n-[2-[(3-fluorophenoxy)methyl]phenyl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1COC1=CC=CC(F)=C1 SFFKWDZELGYSNA-ZRDIBKRKSA-N 0.000 claims 1
- OTZGBNPPNDFITF-NTUHNPAUSA-N (e)-n-[2-[(4-chlorophenoxy)methyl]phenyl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1COC1=CC=C(Cl)C=C1 OTZGBNPPNDFITF-NTUHNPAUSA-N 0.000 claims 1
- RUHVAIKSSFTPIP-NTUHNPAUSA-N (e)-n-[2-[(4-fluorophenoxy)methyl]phenyl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1COC1=CC=C(F)C=C1 RUHVAIKSSFTPIP-NTUHNPAUSA-N 0.000 claims 1
- IQQPECXGYDBLNM-WVLIHFOGSA-N (e)-n-[2-chloro-3-(pyridin-4-ylmethoxy)phenyl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide;hydrochloride Chemical compound Cl.C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC(OCC=2C=CN=CC=2)=C1Cl IQQPECXGYDBLNM-WVLIHFOGSA-N 0.000 claims 1
- BBLYGUKKGNAURU-ACCUITESSA-N (e)-n-[3-(benzylamino)phenyl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC(NCC=2C=CC=CC=2)=C1 BBLYGUKKGNAURU-ACCUITESSA-N 0.000 claims 1
- LLCSDYAPRBPUTK-CSKARUKUSA-N (e)-n-[3-[(2,5-dimethylpyrazol-3-yl)methoxy]phenyl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC(OCC=2N(N=C(C)C=2)C)=C1 LLCSDYAPRBPUTK-CSKARUKUSA-N 0.000 claims 1
- KHGPJNDYHNYHHW-WYMLVPIESA-N (e)-n-[3-[benzyl(methyl)amino]phenyl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC(N(C)CC=2C=CC=CC=2)=C1 KHGPJNDYHNYHHW-WYMLVPIESA-N 0.000 claims 1
- JIZZUQACKKBEFS-SOFGYWHQSA-N (e)-n-[3-chloro-2-(pyridin-4-ylmethoxy)phenyl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC(Cl)=C1OCC1=CC=NC=C1 JIZZUQACKKBEFS-SOFGYWHQSA-N 0.000 claims 1
- QFLAQRPGEFSPII-XVNBXDOJSA-N (e)-n-[4-chloro-3-(pyridin-4-ylmethoxy)phenyl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=C(Cl)C(OCC=2C=CN=CC=2)=C1 QFLAQRPGEFSPII-XVNBXDOJSA-N 0.000 claims 1
- PRURRGMKQXOZHV-XYOKQWHBSA-N (e)-n-[5-chloro-2-(phenoxymethyl)phenyl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)NC1=CC(Cl)=CC=C1COC1=CC=CC=C1 PRURRGMKQXOZHV-XYOKQWHBSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 206010008635 Cholestasis Diseases 0.000 claims 1
- 208000002249 Diabetes Complications Diseases 0.000 claims 1
- 206010012655 Diabetic complications Diseases 0.000 claims 1
- 206010013801 Duchenne Muscular Dystrophy Diseases 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- 102100022745 Laminin subunit alpha-2 Human genes 0.000 claims 1
- 208000021642 Muscular disease Diseases 0.000 claims 1
- 201000009623 Myopathy Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 206010063837 Reperfusion injury Diseases 0.000 claims 1
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims 1
- 206010000891 acute myocardial infarction Diseases 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 206010002026 amyotrophic lateral sclerosis Diseases 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
- 230000007870 cholestasis Effects 0.000 claims 1
- 231100000359 cholestasis Toxicity 0.000 claims 1
- 201000006815 congenital muscular dystrophy Diseases 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 230000006378 damage Effects 0.000 claims 1
- 230000003412 degenerative effect Effects 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- RPIYHWKJBFBIMX-OVGXCEQFSA-L disodium;[5-[(e)-3-(3-chloroanilino)-3-oxoprop-1-enyl]-2-methoxyphenyl] phosphate Chemical compound [Na+].[Na+].C1=C(OP([O-])([O-])=O)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC(Cl)=C1 RPIYHWKJBFBIMX-OVGXCEQFSA-L 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- 229930005346 hydroxycinnamic acid Natural products 0.000 claims 1
- 235000010359 hydroxycinnamic acids Nutrition 0.000 claims 1
- 230000003345 hyperglycaemic effect Effects 0.000 claims 1
- 230000002218 hypoglycaemic effect Effects 0.000 claims 1
- 125000004537 indazol-5-yl group Chemical group N1N=CC2=CC(=CC=C12)* 0.000 claims 1
- 208000037906 ischaemic injury Diseases 0.000 claims 1
- 230000000302 ischemic effect Effects 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 210000000056 organ Anatomy 0.000 claims 1
- 230000004792 oxidative damage Effects 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000008177 pharmaceutical agent Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 239000003223 protective agent Substances 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- NGSWKAQJJWESNS-ZZXKWVIFSA-N trans-4-coumaric acid Chemical compound OC(=O)\C=C\C1=CC=C(O)C=C1 NGSWKAQJJWESNS-ZZXKWVIFSA-N 0.000 claims 1
- 230000009529 traumatic brain injury Effects 0.000 claims 1
- 0 CC(C=C)(C=C1*)C=C(C=CC(N)=O)C=C1O* Chemical compound CC(C=C)(C=C1*)C=C(C=CC(N)=O)C=C1O* 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08018742.0 | 2008-10-27 | ||
| EP08018742A EP2179984A1 (en) | 2008-10-27 | 2008-10-27 | Acrylamido derivatives useful as inhibitors of the mitochondrial permeability transition |
| PCT/IB2009/006939 WO2010049768A1 (en) | 2008-10-27 | 2009-09-23 | Acrylamido derivatives useful as inhibitors of the mitochondrial permeability transition |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014195209A Division JP2015003921A (ja) | 2008-10-27 | 2014-09-25 | ミトコンドリアの膜透過性遷移の阻害剤として有用なアクリルアミド誘導体 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012506852A JP2012506852A (ja) | 2012-03-22 |
| JP2012506852A5 true JP2012506852A5 (https=) | 2013-07-11 |
| JP5670338B2 JP5670338B2 (ja) | 2015-02-18 |
Family
ID=40379729
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011532728A Expired - Fee Related JP5670338B2 (ja) | 2008-10-27 | 2009-09-23 | ミトコンドリアの膜透過性遷移の阻害剤として有用なアクリルアミド誘導体 |
| JP2014195209A Pending JP2015003921A (ja) | 2008-10-27 | 2014-09-25 | ミトコンドリアの膜透過性遷移の阻害剤として有用なアクリルアミド誘導体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014195209A Pending JP2015003921A (ja) | 2008-10-27 | 2014-09-25 | ミトコンドリアの膜透過性遷移の阻害剤として有用なアクリルアミド誘導体 |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US8470831B2 (https=) |
| EP (2) | EP2179984A1 (https=) |
| JP (2) | JP5670338B2 (https=) |
| KR (1) | KR101631342B1 (https=) |
| CN (1) | CN102264693B (https=) |
| AU (1) | AU2009309378B2 (https=) |
| BR (1) | BRPI0920506A2 (https=) |
| CA (1) | CA2741433C (https=) |
| CL (1) | CL2011000903A1 (https=) |
| DK (1) | DK2349982T3 (https=) |
| EA (1) | EA020320B1 (https=) |
| ES (1) | ES2552051T3 (https=) |
| HU (1) | HUE026249T2 (https=) |
| IL (1) | IL212250A (https=) |
| MX (1) | MX2011004363A (https=) |
| NZ (1) | NZ592224A (https=) |
| PL (1) | PL2349982T3 (https=) |
| PT (1) | PT2349982E (https=) |
| SI (1) | SI2349982T1 (https=) |
| UA (1) | UA105018C2 (https=) |
| WO (1) | WO2010049768A1 (https=) |
| ZA (1) | ZA201103047B (https=) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK2035369T3 (da) * | 2006-07-05 | 2014-10-06 | Fibrotech Therapeutics Pty Ltd | Terapeutiske |
| WO2009079692A1 (en) * | 2007-12-21 | 2009-07-02 | Fibrotech Therapeutics Pty Ltd | Halogenated analogues of anti-fibrotic agents |
| EP2179984A1 (en) * | 2008-10-27 | 2010-04-28 | Congenia S.r.l. | Acrylamido derivatives useful as inhibitors of the mitochondrial permeability transition |
| EP2491030B1 (en) | 2009-10-22 | 2015-07-15 | Fibrotech Therapeutics PTY LTD | Fused ring analogues of anti-fibrotic agents |
| WO2012008549A1 (ja) * | 2010-07-15 | 2012-01-19 | 武田薬品工業株式会社 | 複素環化合物 |
| JP5797476B2 (ja) * | 2011-06-24 | 2015-10-21 | 株式会社ダイセル | 不飽和カルボン酸アミド組成物の製造方法 |
| KR101981818B1 (ko) * | 2011-06-24 | 2019-05-23 | 도오꾜오까고오교 가부시끼가이샤 | 신규 화합물 |
| WO2014150318A1 (en) * | 2013-03-15 | 2014-09-25 | Mitochondrial Concepts Llc | Therapeutic agent for enhancing mitochondrial function |
| WO2015191533A1 (en) * | 2014-06-13 | 2015-12-17 | East Carolina University | Methods of using carnosinol and analogs thereof |
| EP2993175A1 (en) | 2014-09-05 | 2016-03-09 | IEO - Istituto Europeo di Oncologia Srl | Thienopyrroles as histone demethylase inhibitors |
| CN105601540B (zh) * | 2016-04-01 | 2017-09-29 | 南阳师范学院 | 一种4‑氨基甲酸酯‑3‑甲氧基肉桂酸苯酰胺类化合物及其制备方法和用途 |
| CN109843896B (zh) * | 2016-10-14 | 2022-12-20 | 波尔图大学 | 羟基肉桂酸衍生物、方法及其用途 |
| PT3565806T (pt) * | 2017-01-06 | 2022-05-19 | Rivus Pharmaceuticals Inc | Novos derivados de fenilo |
| CA3052036A1 (en) * | 2017-02-03 | 2018-08-09 | Certa Therapeutics Pty Ltd. | Anti-fibrotic compounds |
| EP4067453B1 (en) * | 2019-12-26 | 2026-03-25 | Tokyo University of Science Foundation | Photobase generator, compound, photoreactive composition, and reaction product |
| GB202013731D0 (en) * | 2020-09-01 | 2020-10-14 | Nrg Therapeutics Ltd | Novel cmpounds |
| GB202013728D0 (en) | 2020-09-01 | 2020-10-14 | Nrg Therapeutics Ltd | Novel compounds |
| GB202202921D0 (en) | 2022-03-02 | 2022-04-13 | Nrg Therapeutics Ltd | Novel compounds |
| GB202300833D0 (en) | 2023-01-19 | 2023-03-08 | Nrg Therapeutics Ltd | Novel compounds |
| EP4705283A1 (en) * | 2023-06-07 | 2026-03-11 | Beijing Double-Crane Runchuang Technology Co., Ltd. | Imidazolyl binds with dinitrophenyl derivatives and use thereof |
| WO2025052129A1 (en) * | 2023-09-05 | 2025-03-13 | Nrg Therapeutics Ltd | Pyridine derivatives which act as inhibitors of mptp. |
| WO2025107532A1 (en) * | 2023-11-20 | 2025-05-30 | Beijing Double-Crane Runchuang Technology Co., Ltd. | Imidazolyl binds with dinitrophenyl derivatives and use thereof |
| GB202410534D0 (en) * | 2024-07-18 | 2024-09-04 | Nrg Therapeutics Ltd | Novel method and uses |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2832268A1 (de) * | 1978-07-22 | 1980-01-31 | Bayer Ag | Pseudotrisaccharide |
| JP3168915B2 (ja) * | 1995-05-25 | 2001-05-21 | 田辺製薬株式会社 | 医薬組成物 |
| WO1997031900A1 (en) * | 1996-02-29 | 1997-09-04 | Kissei Pharmaceutical Co., Ltd. | Imidazole derivatives and vascular wall thickening inhibitor |
| JP5278983B2 (ja) * | 1999-11-17 | 2013-09-04 | 塩野義製薬株式会社 | アミド化合物の新規用途 |
| US7217722B2 (en) * | 2000-02-01 | 2007-05-15 | Kirin Beer Kabushiki Kaisha | Nitrogen-containing compounds having kinase inhibitory activity and drugs containing the same |
| US20040087798A1 (en) | 2000-03-14 | 2004-05-06 | Akira Yamada | Novel amide compounds |
| US6414013B1 (en) * | 2000-06-19 | 2002-07-02 | Pharmacia & Upjohn S.P.A. | Thiophene compounds, process for preparing the same, and pharmaceutical compositions containing the same background of the invention |
| DE10115994A1 (de) * | 2001-03-30 | 2002-10-10 | Wella Ag | (p-Amino-hydroxyphenyl)acrylamid-Derivate und diese Verbindungen enthaltende Färbemittel |
| US7429593B2 (en) * | 2001-09-14 | 2008-09-30 | Shionogi & Co., Ltd. | Utilities of amide compounds |
| MXPA04005427A (es) | 2001-12-10 | 2005-04-19 | Amgen Inc | Ligandos de receptor vainilloide y su uso en tratamientos. |
| JP4239463B2 (ja) * | 2002-04-09 | 2009-03-18 | 大正製薬株式会社 | ３−トリフルオロメチルアニリド誘導体 |
| AU2003298567B9 (en) | 2002-08-29 | 2009-07-23 | Temple University - Of The Commonwealth System Of Higher Education | Aryl and heteroaryl propene amides, derivatives thereof and therapeutic uses thereof |
| WO2005065361A2 (en) * | 2003-12-31 | 2005-07-21 | Khosrow Kashfi | Compounds and compositions for treating dysproliferative diseases, and methods of use thereof |
| US7671077B2 (en) * | 2004-07-19 | 2010-03-02 | Leu-Fen Hou Lin | Neuroprotective small organic molecules, compositions and uses related thereto |
| AU2006204724A1 (en) * | 2005-01-14 | 2006-07-20 | Millennium Pharmaceuticals, Inc. | Cinnamide and hydrocinnamide derivatives with raf-kinase inhibitory activity |
| JP2008535790A (ja) * | 2005-03-03 | 2008-09-04 | サートリス ファーマシューティカルズ， インコーポレイテッド | サーチュインモジュレーターであるｎ−フェニルベンズアミド誘導体 |
| WO2008028314A1 (fr) * | 2006-08-07 | 2008-03-13 | Lotus Pharmaceutical Co., Ltd. | Dérivés de catéchol, composition et application associées |
| EP2179984A1 (en) * | 2008-10-27 | 2010-04-28 | Congenia S.r.l. | Acrylamido derivatives useful as inhibitors of the mitochondrial permeability transition |
-
2008
- 2008-10-27 EP EP08018742A patent/EP2179984A1/en not_active Withdrawn
-
2009
- 2009-09-23 CA CA2741433A patent/CA2741433C/en not_active Expired - Fee Related
- 2009-09-23 HU HUE09786275A patent/HUE026249T2/en unknown
- 2009-09-23 DK DK09786275.9T patent/DK2349982T3/en active
- 2009-09-23 PL PL09786275T patent/PL2349982T3/pl unknown
- 2009-09-23 ES ES09786275.9T patent/ES2552051T3/es active Active
- 2009-09-23 EP EP09786275.9A patent/EP2349982B1/en active Active
- 2009-09-23 SI SI200931298T patent/SI2349982T1/sl unknown
- 2009-09-23 AU AU2009309378A patent/AU2009309378B2/en not_active Ceased
- 2009-09-23 CN CN200980153139.7A patent/CN102264693B/zh not_active Expired - Fee Related
- 2009-09-23 JP JP2011532728A patent/JP5670338B2/ja not_active Expired - Fee Related
- 2009-09-23 EA EA201170607A patent/EA020320B1/ru not_active IP Right Cessation
- 2009-09-23 WO PCT/IB2009/006939 patent/WO2010049768A1/en not_active Ceased
- 2009-09-23 PT PT97862759T patent/PT2349982E/pt unknown
- 2009-09-23 MX MX2011004363A patent/MX2011004363A/es active IP Right Grant
- 2009-09-23 KR KR1020117011830A patent/KR101631342B1/ko not_active Expired - Fee Related
- 2009-09-23 NZ NZ592224A patent/NZ592224A/xx not_active IP Right Cessation
- 2009-09-23 US US13/123,852 patent/US8470831B2/en not_active Expired - Fee Related
- 2009-09-23 UA UAA201106556A patent/UA105018C2/uk unknown
- 2009-09-23 BR BRPI0920506A patent/BRPI0920506A2/pt not_active Application Discontinuation
-
2011
- 2011-04-11 IL IL212250A patent/IL212250A/en not_active IP Right Cessation
- 2011-04-21 ZA ZA2011/03047A patent/ZA201103047B/en unknown
- 2011-04-21 CL CL2011000903A patent/CL2011000903A1/es unknown
-
2013
- 2013-04-30 US US13/874,081 patent/US8669261B2/en not_active Expired - Fee Related
-
2014
- 2014-09-25 JP JP2014195209A patent/JP2015003921A/ja active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2012506852A5 (https=) | ||
| ES2552051T3 (es) | Derivados de acrilamido útiles como inhibidores de la transición de la permeabilidad mitocondrial | |
| DE3781845T2 (de) | Benzimidazol-derivate. | |
| CA2754613C (en) | Piperazine compound capable of inhibiting prostaglandin d synthase | |
| JP2011504485A5 (https=) | ||
| JP2013513605A5 (https=) | ||
| JP2010501587A5 (https=) | ||
| ZA200503989B (en) | Mandelic acid derivatives | |
| JP2004538285A5 (https=) | ||
| SK1142003A3 (en) | Carboxamide compounds and their use as antagonists of a human 11CBY receptor | |
| WO2001025190A1 (en) | Novel diarylamide derivatives and use thereof as medicines | |
| JP2009537544A5 (https=) | ||
| CA1205470A (en) | Dihydropyridines | |
| RU2014121394A (ru) | Двузамещенные соединения диамино-3,4-циклобутен-3-диона-1,2, приемлемые для лечения паталогий, опосредованных хемокинами | |
| NZ552501A (en) | Novel cyclic aminobenzoic acid derivative | |
| JP2009545549A5 (https=) | ||
| JP2009040767A5 (https=) | ||
| JP2024514366A (ja) | 可溶性エポキシドヒドロラーゼ阻害剤としてのピペリジン尿素誘導体 | |
| JP2008542365A5 (https=) | ||
| JP2010053115A (ja) | 新規フェニルアセテート誘導体またはその薬学的に許容可能な塩、その製造方法及びそれを有効成分として含むｔ−型カルシウムイオンチャンネルの活性によって誘発される疾患の予防または治療用組成物 | |
| EP2207776B9 (en) | Drug active in neuropathic pain | |
| CA2608837A1 (en) | Sulfonamide derivatives useful as liver carnitine palmitoyl transferase (l-cpt1) inhibitors | |
| EP3327001A1 (en) | Novel compound having blt inhibitory activity and composition, for preventing or treating inflammatory diseases, comprising same as active ingredient | |
| HU0501139D0 (en) | An optically active carbamic acid derivative, method for producing the same and use as a pharmaceutical intermediate | |
| WO2003004020A1 (de) | Heteroarylcarbonsäureamide, ihre herstellung und ihre verwendung als inhibitoren des mikrosmalen triglycerid-transferproteins (mtp) |