JP2010513387A5 - - Google Patents
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- Publication number
- JP2010513387A5 JP2010513387A5 JP2009542019A JP2009542019A JP2010513387A5 JP 2010513387 A5 JP2010513387 A5 JP 2010513387A5 JP 2009542019 A JP2009542019 A JP 2009542019A JP 2009542019 A JP2009542019 A JP 2009542019A JP 2010513387 A5 JP2010513387 A5 JP 2010513387A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- chloro
- acrylamide
- trifluoromethyl
- amino
- 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.)
- Abandoned
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- -1 methyl-sulfonyl-amino, phenyl-sulfonyl-amino, N-methyl-sulfonyl-carboxamide Chemical compound 0.000 claims 20
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- 239000001257 hydrogen Substances 0.000 claims 14
- 125000001475 halogen functional group Chemical group 0.000 claims 13
- 125000003118 aryl group Chemical group 0.000 claims 11
- APEJMQOBVMLION-UHFFFAOYSA-N cinnamamide Chemical class NC(=O)C=CC1=CC=CC=C1 APEJMQOBVMLION-UHFFFAOYSA-N 0.000 claims 9
- 239000003814 drug Substances 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 125000000850 2H-chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 229940079593 drug Drugs 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
- 208000035475 disorder Diseases 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims 5
- 206010010904 Convulsion Diseases 0.000 claims 4
- 125000002837 carbocyclic group Chemical group 0.000 claims 4
- 210000003038 endothelium Anatomy 0.000 claims 4
- 230000002102 hyperpolarization Effects 0.000 claims 4
- 230000001404 mediated effect Effects 0.000 claims 4
- 239000002571 phosphodiesterase inhibitor Substances 0.000 claims 4
- APEJMQOBVMLION-VOTSOKGWSA-N trans-cinnamamide Chemical class NC(=O)\C=C\C1=CC=CC=C1 APEJMQOBVMLION-VOTSOKGWSA-N 0.000 claims 4
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims 3
- 229940099471 Phosphodiesterase inhibitor Drugs 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000001041 indolyl group Chemical group 0.000 claims 3
- HWJRQTQRAADPIC-UHFFFAOYSA-N n-cyanoformamide Chemical group O=CNC#N HWJRQTQRAADPIC-UHFFFAOYSA-N 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- 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 2
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims 2
- 208000010228 Erectile Dysfunction Diseases 0.000 claims 2
- 208000028017 Psychotic disease Diseases 0.000 claims 2
- 201000001880 Sexual dysfunction Diseases 0.000 claims 2
- 206010049447 Tachyarrhythmia Diseases 0.000 claims 2
- 208000001871 Tachycardia Diseases 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
- 206010003119 arrhythmia Diseases 0.000 claims 2
- 125000002527 bicyclic carbocyclic group Chemical group 0.000 claims 2
- 229930016911 cinnamic acid Natural products 0.000 claims 2
- 235000013985 cinnamic acid Nutrition 0.000 claims 2
- 230000006735 deficit Effects 0.000 claims 2
- 230000001079 digestive effect Effects 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 206010013781 dry mouth Diseases 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 201000001881 impotence Diseases 0.000 claims 2
- 208000028867 ischemia Diseases 0.000 claims 2
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- CNDIHLBEKKVGNA-UHFFFAOYSA-N n-(benzenesulfonyl)formamide Chemical compound O=CNS(=O)(=O)C1=CC=CC=C1 CNDIHLBEKKVGNA-UHFFFAOYSA-N 0.000 claims 2
- QFBHCGFWZVVHSV-UHFFFAOYSA-N nitramidoperoxysulfonylformic acid Chemical compound [N+](=O)([O-])NOOS(=O)(=O)C(=O)O QFBHCGFWZVVHSV-UHFFFAOYSA-N 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 231100000872 sexual dysfunction Toxicity 0.000 claims 2
- BNRNXUUZRGQAQC-UHFFFAOYSA-N sildenafil Chemical compound CCCC1=NN(C)C(C(N2)=O)=C1N=C2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(C)CC1 BNRNXUUZRGQAQC-UHFFFAOYSA-N 0.000 claims 2
- LHELHSNLJXKBCT-DAFODLJHSA-N (e)-3-[3,5-bis(trifluoromethyl)phenyl]-n-(5-chloro-2-hydroxyphenyl)prop-2-enamide Chemical compound OC1=CC=C(Cl)C=C1NC(=O)\C=C\C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 LHELHSNLJXKBCT-DAFODLJHSA-N 0.000 claims 1
- KJTPYXJGKLLESS-UNXLUWIOSA-N (e)-3-[3,5-bis(trifluoromethyl)phenyl]-n-[4-(4-chlorophenyl)-2-(2h-tetrazol-5-yl)phenyl]prop-2-enamide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(\C=C\C(=O)NC=2C(=CC(=CC=2)C=2C=CC(Cl)=CC=2)C2=NNN=N2)=C1 KJTPYXJGKLLESS-UNXLUWIOSA-N 0.000 claims 1
- UMFVYBSAWGXCRC-DAFODLJHSA-N (e)-3-[3,5-bis(trifluoromethyl)phenyl]-n-[4-bromo-2-(2h-tetrazol-5-yl)phenyl]prop-2-enamide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(\C=C\C(=O)NC=2C(=CC(Br)=CC=2)C=2NN=NN=2)=C1 UMFVYBSAWGXCRC-DAFODLJHSA-N 0.000 claims 1
- METVFLYABXYWRS-DAFODLJHSA-N (e)-3-[3,5-bis(trifluoromethyl)phenyl]-n-[4-iodo-2-(2h-tetrazol-5-yl)phenyl]prop-2-enamide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(\C=C\C(=O)NC=2C(=CC(I)=CC=2)C=2NN=NN=2)=C1 METVFLYABXYWRS-DAFODLJHSA-N 0.000 claims 1
- OCUZIRLHOOTBNO-ZRDIBKRKSA-N (e)-3-naphthalen-2-yl-n-[2-(2h-tetrazol-5-yl)phenyl]prop-2-enamide Chemical compound C=1C=C2C=CC=CC2=CC=1/C=C/C(=O)NC1=CC=CC=C1C1=NN=NN1 OCUZIRLHOOTBNO-ZRDIBKRKSA-N 0.000 claims 1
- XYQDIFBKCINHCF-YRNVUSSQSA-N (e)-n-(2-acetamido-5-chlorophenyl)-3-naphthalen-2-ylprop-2-enamide Chemical compound CC(=O)NC1=CC=C(Cl)C=C1NC(=O)\C=C\C1=CC=C(C=CC=C2)C2=C1 XYQDIFBKCINHCF-YRNVUSSQSA-N 0.000 claims 1
- GKLWGEQHPOUYIW-UXBLZVDNSA-N (e)-n-(2-amino-5-chlorophenyl)-3-naphthalen-2-ylprop-2-enamide Chemical compound NC1=CC=C(Cl)C=C1NC(=O)\C=C\C1=CC=C(C=CC=C2)C2=C1 GKLWGEQHPOUYIW-UXBLZVDNSA-N 0.000 claims 1
- GOHHTOVBDFWFQT-QPJJXVBHSA-N (e)-n-(5-chloro-2-hydroxyphenyl)-3-(3-nitrophenyl)prop-2-enamide Chemical compound OC1=CC=C(Cl)C=C1NC(=O)\C=C\C1=CC=CC([N+]([O-])=O)=C1 GOHHTOVBDFWFQT-QPJJXVBHSA-N 0.000 claims 1
- RNIYQJCUEVEEOS-UXBLZVDNSA-N (e)-n-(5-chloro-2-nitrophenyl)-3-naphthalen-2-ylprop-2-enamide Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1NC(=O)\C=C\C1=CC=C(C=CC=C2)C2=C1 RNIYQJCUEVEEOS-UXBLZVDNSA-N 0.000 claims 1
- TXTRITGPFAHELV-SOFGYWHQSA-N (e)-n-(5-chloro-4-fluoro-2-sulfamoylphenyl)-3-naphthalen-2-ylprop-2-enamide Chemical compound NS(=O)(=O)C1=CC(F)=C(Cl)C=C1NC(=O)\C=C\C1=CC=C(C=CC=C2)C2=C1 TXTRITGPFAHELV-SOFGYWHQSA-N 0.000 claims 1
- NDZLDFGRKNEKOT-ZRDIBKRKSA-N (e)-n-[2-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl]-3-naphthalen-2-ylprop-2-enamide Chemical compound FC(F)(F)C(C(F)(F)F)(O)C1=CC=CC=C1NC(=O)\C=C\C1=CC=C(C=CC=C2)C2=C1 NDZLDFGRKNEKOT-ZRDIBKRKSA-N 0.000 claims 1
- GGQHARTUXHZVNH-RVDMUPIBSA-N (e)-n-[2-(benzenesulfonamido)-5-chlorophenyl]-3-naphthalen-2-ylprop-2-enamide Chemical compound C=1C=C2C=CC=CC2=CC=1/C=C/C(=O)NC1=CC(Cl)=CC=C1NS(=O)(=O)C1=CC=CC=C1 GGQHARTUXHZVNH-RVDMUPIBSA-N 0.000 claims 1
- YHCUGJVPCCXXOF-QPJJXVBHSA-N (e)-n-[4-bromo-2-(2h-tetrazol-5-yl)phenyl]-3-[3-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound FC(F)(F)C1=CC=CC(\C=C\C(=O)NC=2C(=CC(Br)=CC=2)C=2NN=NN=2)=C1 YHCUGJVPCCXXOF-QPJJXVBHSA-N 0.000 claims 1
- KRWFSTSSTRVBNH-UXBLZVDNSA-N (e)-n-[4-bromo-2-(2h-tetrazol-5-yl)phenyl]-3-naphthalen-2-ylprop-2-enamide Chemical compound C=1C(Br)=CC=C(NC(=O)\C=C\C=2C=C3C=CC=CC3=CC=2)C=1C1=NN=NN1 KRWFSTSSTRVBNH-UXBLZVDNSA-N 0.000 claims 1
- MSKGZYOWCMVRKC-QHHAFSJGSA-N (e)-n-[5-chloro-2-(2h-tetrazol-5-yl)phenyl]-3-(3,4-dichlorophenyl)prop-2-enamide Chemical compound C=1C=C(Cl)C(Cl)=CC=1/C=C/C(=O)NC1=CC(Cl)=CC=C1C1=NN=NN1 MSKGZYOWCMVRKC-QHHAFSJGSA-N 0.000 claims 1
- GCPIOGNMWMOGDF-QHHAFSJGSA-N (e)-n-[5-chloro-2-(2h-tetrazol-5-yl)phenyl]-3-[4-fluoro-3-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1\C=C\C(=O)NC1=CC(Cl)=CC=C1C1=NN=NN1 GCPIOGNMWMOGDF-QHHAFSJGSA-N 0.000 claims 1
- CGZOSWPLTVPHKY-UXBLZVDNSA-N (e)-n-[5-chloro-2-(2h-tetrazol-5-yl)phenyl]-3-naphthalen-2-ylprop-2-enamide Chemical compound C=1C=C2C=CC=CC2=CC=1/C=C/C(=O)NC1=CC(Cl)=CC=C1C1=NN=NN1 CGZOSWPLTVPHKY-UXBLZVDNSA-N 0.000 claims 1
- AZHSJTNBTLJFMA-UXBLZVDNSA-N (e)-n-[5-chloro-2-(2h-tetrazol-5-ylmethoxy)phenyl]-3-naphthalen-2-ylprop-2-enamide Chemical compound C=1C=C2C=CC=CC2=CC=1/C=C/C(=O)NC1=CC(Cl)=CC=C1OCC1=NN=NN1 AZHSJTNBTLJFMA-UXBLZVDNSA-N 0.000 claims 1
- RPMTVICURJNLOI-UXBLZVDNSA-N (e)-n-[5-chloro-2-(5-oxo-2h-1,2,4-oxadiazol-3-yl)phenyl]-3-naphthalen-2-ylprop-2-enamide Chemical compound C=1C=C2C=CC=CC2=CC=1/C=C/C(=O)NC1=CC(Cl)=CC=C1C1=NOC(=O)N1 RPMTVICURJNLOI-UXBLZVDNSA-N 0.000 claims 1
- YSBXUYYPPGONLP-YRNVUSSQSA-N (e)-n-[5-chloro-2-(methanesulfonamido)phenyl]-3-naphthalen-2-ylprop-2-enamide Chemical compound CS(=O)(=O)NC1=CC=C(Cl)C=C1NC(=O)\C=C\C1=CC=C(C=CC=C2)C2=C1 YSBXUYYPPGONLP-YRNVUSSQSA-N 0.000 claims 1
- SFNWSPBFQRRTFZ-UXBLZVDNSA-N (e)-n-[5-chloro-2-(trifluoromethylsulfonylamino)phenyl]-3-naphthalen-2-ylprop-2-enamide Chemical compound FC(F)(F)S(=O)(=O)NC1=CC=C(Cl)C=C1NC(=O)\C=C\C1=CC=C(C=CC=C2)C2=C1 SFNWSPBFQRRTFZ-UXBLZVDNSA-N 0.000 claims 1
- LKBLPSKMSDFDBS-UXBLZVDNSA-N (e)-n-[5-chloro-2-[(2,2,2-trifluoroacetyl)amino]phenyl]-3-naphthalen-2-ylprop-2-enamide Chemical compound FC(F)(F)C(=O)NC1=CC=C(Cl)C=C1NC(=O)\C=C\C1=CC=C(C=CC=C2)C2=C1 LKBLPSKMSDFDBS-UXBLZVDNSA-N 0.000 claims 1
- VKGKURAONZTKHE-SOFGYWHQSA-N 4,5-dichloro-2-[[(e)-3-naphthalen-2-ylprop-2-enoyl]amino]benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC(Cl)=C(Cl)C=C1NC(=O)\C=C\C1=CC=C(C=CC=C2)C2=C1 VKGKURAONZTKHE-SOFGYWHQSA-N 0.000 claims 1
- NYQJPNKIXZIYMC-QHHAFSJGSA-N 4-chloro-2-[[(e)-3-(3,4-dichlorophenyl)prop-2-enoyl]amino]benzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1NC(=O)\C=C\C1=CC=C(Cl)C(Cl)=C1 NYQJPNKIXZIYMC-QHHAFSJGSA-N 0.000 claims 1
- YYLDFEJXZPESJV-MDWZMJQESA-N 4-chloro-2-[[(e)-3-(4-phenylphenyl)prop-2-enoyl]amino]benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C=C1NC(=O)\C=C\C1=CC=C(C=2C=CC=CC=2)C=C1 YYLDFEJXZPESJV-MDWZMJQESA-N 0.000 claims 1
- MCTLJAYSEVDVST-UXBLZVDNSA-N 4-chloro-2-[[(e)-3-naphthalen-2-ylprop-2-enoyl]amino]benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C=C1NC(=O)\C=C\C1=CC=C(C=CC=C2)C2=C1 MCTLJAYSEVDVST-UXBLZVDNSA-N 0.000 claims 1
- BWQMBZRZVQFRQA-UXBLZVDNSA-N 4-chloro-2-[[(e)-3-naphthalen-2-ylprop-2-enoyl]amino]benzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1NC(=O)\C=C\C1=CC=C(C=CC=C2)C2=C1 BWQMBZRZVQFRQA-UXBLZVDNSA-N 0.000 claims 1
- XUXXXFKCRITRJH-UXBLZVDNSA-N 4-chloro-n-cyano-2-[[(e)-3-naphthalen-2-ylprop-2-enoyl]amino]benzamide Chemical compound ClC1=CC=C(C(=O)NC#N)C(NC(=O)\C=C\C=2C=C3C=CC=CC3=CC=2)=C1 XUXXXFKCRITRJH-UXBLZVDNSA-N 0.000 claims 1
- VRHIQTXQOPZMJT-YRNVUSSQSA-N 4-chloro-n-methylsulfonyl-2-[[(e)-3-naphthalen-2-ylprop-2-enoyl]amino]benzamide Chemical compound CS(=O)(=O)NC(=O)C1=CC=C(Cl)C=C1NC(=O)\C=C\C1=CC=C(C=CC=C2)C2=C1 VRHIQTXQOPZMJT-YRNVUSSQSA-N 0.000 claims 1
- YKTHAFZGSUNUTG-UHFFFAOYSA-N 5-chloro-n-[4-(4-fluorophenyl)-2-(2h-tetrazol-5-yl)phenyl]-1h-indole-2-carboxamide Chemical compound C1=CC(F)=CC=C1C(C=C1C=2NN=NN=2)=CC=C1NC(=O)C1=CC2=CC(Cl)=CC=C2N1 YKTHAFZGSUNUTG-UHFFFAOYSA-N 0.000 claims 1
- NAVPOCOMTPRCOC-UHFFFAOYSA-N 5-chloro-n-[5-chloro-2-(2h-tetrazol-5-yl)phenyl]-1h-indole-2-carboxamide Chemical compound C=1C2=CC(Cl)=CC=C2NC=1C(=O)NC1=CC(Cl)=CC=C1C1=NN=NN1 NAVPOCOMTPRCOC-UHFFFAOYSA-N 0.000 claims 1
- LLGQLYYIIMJCTK-UHFFFAOYSA-N 6-bromo-n-[5-chloro-2-(2h-tetrazol-5-yl)phenyl]-2-oxochromene-3-carboxamide Chemical compound C=1C2=CC(Br)=CC=C2OC(=O)C=1C(=O)NC1=CC(Cl)=CC=C1C1=NN=NN1 LLGQLYYIIMJCTK-UHFFFAOYSA-N 0.000 claims 1
- JWSLATHFQAEULD-UHFFFAOYSA-N 6-chloro-n-[5-chloro-2-(2h-tetrazol-5-yl)phenyl]-2h-chromene-3-carboxamide Chemical compound C=1C2=CC(Cl)=CC=C2OCC=1C(=O)NC1=CC(Cl)=CC=C1C1=NN=NN1 JWSLATHFQAEULD-UHFFFAOYSA-N 0.000 claims 1
- 201000004384 Alopecia Diseases 0.000 claims 1
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- 206010003225 Arteriospasm coronary Diseases 0.000 claims 1
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- 206010003805 Autism Diseases 0.000 claims 1
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- 201000006474 Brain Ischemia Diseases 0.000 claims 1
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- 206010007572 Cardiac hypertrophy Diseases 0.000 claims 1
- 208000006029 Cardiomegaly Diseases 0.000 claims 1
- 208000031229 Cardiomyopathies Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
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- 241000124008 Mammalia Species 0.000 claims 1
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- 206010054048 Postoperative ileus Diseases 0.000 claims 1
- 102000004257 Potassium Channel Human genes 0.000 claims 1
- 208000005107 Premature Birth Diseases 0.000 claims 1
- 206010036590 Premature baby Diseases 0.000 claims 1
- 208000003782 Raynaud disease Diseases 0.000 claims 1
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- 208000036071 Rhinorrhea Diseases 0.000 claims 1
- 206010039101 Rhinorrhoea Diseases 0.000 claims 1
- 208000021386 Sjogren Syndrome Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 1
- 208000003800 Urinary Bladder Neck Obstruction Diseases 0.000 claims 1
- 206010046543 Urinary incontinence Diseases 0.000 claims 1
- 208000026723 Urinary tract disease Diseases 0.000 claims 1
- SECKRCOLJRRGGV-UHFFFAOYSA-N Vardenafil Chemical compound CCCC1=NC(C)=C(C(N=2)=O)N1NC=2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(CC)CC1 SECKRCOLJRRGGV-UHFFFAOYSA-N 0.000 claims 1
- 206010047163 Vasospasm Diseases 0.000 claims 1
- 206010047281 Ventricular arrhythmia Diseases 0.000 claims 1
- 206010065341 Ventricular tachyarrhythmia Diseases 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 208000028311 absence seizure Diseases 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 230000006793 arrhythmia Effects 0.000 claims 1
- 230000001746 atrial effect Effects 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 208000028683 bipolar I disease Diseases 0.000 claims 1
- 208000006218 bradycardia Diseases 0.000 claims 1
- 229960005438 calcium dobesilate Drugs 0.000 claims 1
- QGNBTYAQAPLTMX-UHFFFAOYSA-L calcium dobesilate Chemical compound [Ca+2].OC1=CC=C(O)C(S([O-])(=O)=O)=C1.OC1=CC=C(O)C(S([O-])(=O)=O)=C1 QGNBTYAQAPLTMX-UHFFFAOYSA-L 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
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| DKPA200601657 | 2006-12-18 | ||
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| DKPA200700481 | 2007-03-28 | ||
| PCT/EP2007/064015 WO2008074755A2 (en) | 2006-12-18 | 2007-12-17 | Novel cinnamic amide derivatives useful as ion channel modulators |
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| JP2010513387A JP2010513387A (ja) | 2010-04-30 |
| JP2010513387A5 true JP2010513387A5 (cg-RX-API-DMAC7.html) | 2011-02-10 |
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| EP (1) | EP2121569A2 (cg-RX-API-DMAC7.html) |
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| US9198886B2 (en) * | 2006-08-16 | 2015-12-01 | Pedro Cuevas Sánchez | Use of 2,5-dihydroxybenzene for the treatment of ocular diseases |
| CN102643207A (zh) * | 2011-02-21 | 2012-08-22 | 南京农业大学 | 3-(2-萘基)丙烯酰胺类衍生物及其制备方法与用途 |
| CN102258508A (zh) * | 2011-04-14 | 2011-11-30 | 威海迪素制药有限公司 | 芳基丙烯酸衍生物抗癫痫的用途 |
| CN117045648A (zh) * | 2023-09-07 | 2023-11-14 | 复旦大学 | Bk通道开放剂在用于治疗骨质疏松症中的应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US3158610A (en) * | 1964-01-03 | 1964-11-24 | American Cyanamid Co | 2-styrylbenzoxazole brighteners |
| DE1670908A1 (de) * | 1967-08-16 | 1971-04-29 | Hoechst Ag | Neue Benzimidazolverbindungen,Verfahren zu ihrer Herstellung und ihre Verwendung als optische Aufhellungsmittel |
| US6127392A (en) * | 1997-08-05 | 2000-10-03 | American Home Products Corporation | Anthranilic acid analogs |
| US6046239A (en) * | 1997-08-05 | 2000-04-04 | American Home Products Corporation | Anthranilic acid analogs |
| AR034897A1 (es) * | 2001-08-07 | 2004-03-24 | Hoffmann La Roche | Derivados n-monoacilados de o-fenilendiaminas, sus analogos heterociclicos de seis miembros y su uso como agentes farmaceuticos |
| JP3835749B2 (ja) * | 2002-04-15 | 2006-10-18 | 日本曹達株式会社 | フェノール性化合物を用いた記録材料 |
| WO2003091213A1 (en) * | 2002-04-25 | 2003-11-06 | Yamanouchi Pharmaceutical Co., Ltd. | Novel amide derivatives or salts thereof |
| AU2003258491A1 (en) * | 2002-09-05 | 2004-03-29 | Neurosearch A/S | Amide derivatives and their use as chloride channel blockers |
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- 2007-12-17 EP EP07857649A patent/EP2121569A2/en not_active Withdrawn
- 2007-12-17 JP JP2009542019A patent/JP2010513387A/ja not_active Abandoned
- 2007-12-17 WO PCT/EP2007/064015 patent/WO2008074755A2/en not_active Ceased
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