JP2009518292A5 - - Google Patents
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- Publication number
- JP2009518292A5 JP2009518292A5 JP2008542778A JP2008542778A JP2009518292A5 JP 2009518292 A5 JP2009518292 A5 JP 2009518292A5 JP 2008542778 A JP2008542778 A JP 2008542778A JP 2008542778 A JP2008542778 A JP 2008542778A JP 2009518292 A5 JP2009518292 A5 JP 2009518292A5
- Authority
- JP
- Japan
- Prior art keywords
- benzimidazol
- biphenyl
- ethylamine
- ethyl
- methoxy
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 206010047700 Vomiting Diseases 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 230000008673 vomiting Effects 0.000 claims 4
- 208000020925 Bipolar disease Diseases 0.000 claims 3
- 206010010904 Convulsion Diseases 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 150000001204 N-oxides Chemical class 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- -1 methylenedioxy, ethylenedioxy Chemical group 0.000 claims 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 208000008811 Agoraphobia Diseases 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 201000006474 Brain Ischemia Diseases 0.000 claims 2
- 206010008120 Cerebral ischaemia Diseases 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 206010008118 cerebral infarction Diseases 0.000 claims 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 208000024714 major depressive disease Diseases 0.000 claims 2
- 208000004296 neuralgia Diseases 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 208000019906 panic disease Diseases 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 208000011117 substance-related disease Diseases 0.000 claims 2
- CJKRCJXOIXCMQV-OAHLLOKOSA-N (1r)-1-[1-(3-phenylphenyl)benzimidazol-5-yl]ethanamine Chemical compound C1=NC2=CC([C@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1 CJKRCJXOIXCMQV-OAHLLOKOSA-N 0.000 claims 1
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- WPOMEYIQKVWZFV-OAHLLOKOSA-N (1r)-1-[1-[3-(2,4-dimethoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=CC(OC)=CC=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@@H](C)N)=C1 WPOMEYIQKVWZFV-OAHLLOKOSA-N 0.000 claims 1
- MZWSTKBMZXQVOO-CYBMUJFWSA-N (1r)-1-[1-[3-(2,6-dichlorophenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound C1=NC2=CC([C@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=C(Cl)C=CC=C1Cl MZWSTKBMZXQVOO-CYBMUJFWSA-N 0.000 claims 1
- GLCNXFUJTTUNSL-CYBMUJFWSA-N (1r)-1-[1-[3-(2,6-difluorophenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound C1=NC2=CC([C@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=C(F)C=CC=C1F GLCNXFUJTTUNSL-CYBMUJFWSA-N 0.000 claims 1
- DZOIOTNHUXUDGQ-OAHLLOKOSA-N (1r)-1-[1-[3-(2,6-dimethoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@@H](C)N)=C1 DZOIOTNHUXUDGQ-OAHLLOKOSA-N 0.000 claims 1
- NPPYMOZIWZOUSL-CQSZACIVSA-N (1r)-1-[1-[3-(2-chloro-6-fluoro-3-methylphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound C1=NC2=CC([C@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=C(F)C=CC(C)=C1Cl NPPYMOZIWZOUSL-CQSZACIVSA-N 0.000 claims 1
- KWLIBQUJFONRSM-CQSZACIVSA-N (1r)-1-[1-[3-(2-chloro-6-methoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=CC=CC(Cl)=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@@H](C)N)=C1 KWLIBQUJFONRSM-CQSZACIVSA-N 0.000 claims 1
- FGERINFNQINSMH-CQSZACIVSA-N (1r)-1-[1-[3-(2-fluoro-6-methoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=CC=CC(F)=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@@H](C)N)=C1 FGERINFNQINSMH-CQSZACIVSA-N 0.000 claims 1
- VPHQMUURAIOPTJ-OAHLLOKOSA-N (1r)-1-[1-[3-(2-methoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=CC=CC=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@@H](C)N)=C1 VPHQMUURAIOPTJ-OAHLLOKOSA-N 0.000 claims 1
- WXYBWPPRLHMCCR-GOSISDBHSA-N (1r)-1-[1-[3-(2-piperazin-1-ylphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound C1=NC2=CC([C@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1N1CCNCC1 WXYBWPPRLHMCCR-GOSISDBHSA-N 0.000 claims 1
- DWWPQNSBCRBVNY-CYBMUJFWSA-N (1r)-1-[1-[3-(3,5-difluoro-2-methoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=C(F)C=C(F)C=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@@H](C)N)=C1 DWWPQNSBCRBVNY-CYBMUJFWSA-N 0.000 claims 1
- QDLHGPWPNGLLCA-CQSZACIVSA-N (1r)-1-[1-[3-(3-chloro-2-methoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=C(Cl)C=CC=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@@H](C)N)=C1 QDLHGPWPNGLLCA-CQSZACIVSA-N 0.000 claims 1
- LQAWDGAFBLVCGO-CQSZACIVSA-N (1r)-1-[1-[3-(3-fluoro-2-methoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=C(F)C=CC=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@@H](C)N)=C1 LQAWDGAFBLVCGO-CQSZACIVSA-N 0.000 claims 1
- ROUPFXQEQBKISE-CQSZACIVSA-N (1r)-1-[1-[3-(4-fluoro-2-methoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=CC(F)=CC=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@@H](C)N)=C1 ROUPFXQEQBKISE-CQSZACIVSA-N 0.000 claims 1
- OGQNTQKGAMZNDT-CQSZACIVSA-N (1r)-1-[1-[3-(5-chloro-2-methoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=CC=C(Cl)C=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@@H](C)N)=C1 OGQNTQKGAMZNDT-CQSZACIVSA-N 0.000 claims 1
- DOHDMDZZTAULIV-CQSZACIVSA-N (1r)-1-[1-[3-(5-fluoro-2-methoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=CC=C(F)C=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@@H](C)N)=C1 DOHDMDZZTAULIV-CQSZACIVSA-N 0.000 claims 1
- VIROKERMYCAYND-CQSZACIVSA-N (1r)-1-[1-[3-(6-chloro-2-fluoro-3-methylphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound C1=NC2=CC([C@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=C(Cl)C=CC(C)=C1F VIROKERMYCAYND-CQSZACIVSA-N 0.000 claims 1
- VOXSQTUIFNZBGV-LJQANCHMSA-N (1r)-1-[1-[3-[2-(morpholin-4-ylmethyl)phenyl]phenyl]benzimidazol-5-yl]ethanamine Chemical compound C1=NC2=CC([C@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1CN1CCOCC1 VOXSQTUIFNZBGV-LJQANCHMSA-N 0.000 claims 1
- AUGQXCMJYAPTJI-CQSZACIVSA-N (1r)-1-[1-[3-[2-(trifluoromethoxy)phenyl]phenyl]benzimidazol-5-yl]ethanamine Chemical compound C1=NC2=CC([C@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1OC(F)(F)F AUGQXCMJYAPTJI-CQSZACIVSA-N 0.000 claims 1
- CJKRCJXOIXCMQV-HNNXBMFYSA-N (1s)-1-[1-(3-phenylphenyl)benzimidazol-5-yl]ethanamine Chemical compound C1=NC2=CC([C@@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1 CJKRCJXOIXCMQV-HNNXBMFYSA-N 0.000 claims 1
- ZKJDXSBGJFPJLC-AWEZNQCLSA-N (1s)-1-[1-[3-(1,3-benzodioxol-4-yl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound C1=NC2=CC([C@@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC2=C1OCO2 ZKJDXSBGJFPJLC-AWEZNQCLSA-N 0.000 claims 1
- TUYYWNHWWSDRIQ-ZDUSSCGKSA-N (1s)-1-[1-[3-(2,3-difluoro-6-methoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=CC=C(F)C(F)=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@H](C)N)=C1 TUYYWNHWWSDRIQ-ZDUSSCGKSA-N 0.000 claims 1
- YOSFSEAGAQAXBO-HNNXBMFYSA-N (1s)-1-[1-[3-(2,3-dimethoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=CC=CC(C=2C=C(C=CC=2)N2C3=CC=C(C=C3N=C2)[C@H](C)N)=C1OC YOSFSEAGAQAXBO-HNNXBMFYSA-N 0.000 claims 1
- WPOMEYIQKVWZFV-HNNXBMFYSA-N (1s)-1-[1-[3-(2,4-dimethoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=CC(OC)=CC=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@H](C)N)=C1 WPOMEYIQKVWZFV-HNNXBMFYSA-N 0.000 claims 1
- MZWSTKBMZXQVOO-ZDUSSCGKSA-N (1s)-1-[1-[3-(2,6-dichlorophenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound C1=NC2=CC([C@@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=C(Cl)C=CC=C1Cl MZWSTKBMZXQVOO-ZDUSSCGKSA-N 0.000 claims 1
- GLCNXFUJTTUNSL-ZDUSSCGKSA-N (1s)-1-[1-[3-(2,6-difluorophenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound C1=NC2=CC([C@@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=C(F)C=CC=C1F GLCNXFUJTTUNSL-ZDUSSCGKSA-N 0.000 claims 1
- DZOIOTNHUXUDGQ-HNNXBMFYSA-N (1s)-1-[1-[3-(2,6-dimethoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@H](C)N)=C1 DZOIOTNHUXUDGQ-HNNXBMFYSA-N 0.000 claims 1
- NPPYMOZIWZOUSL-AWEZNQCLSA-N (1s)-1-[1-[3-(2-chloro-6-fluoro-3-methylphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound C1=NC2=CC([C@@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=C(F)C=CC(C)=C1Cl NPPYMOZIWZOUSL-AWEZNQCLSA-N 0.000 claims 1
- KWLIBQUJFONRSM-AWEZNQCLSA-N (1s)-1-[1-[3-(2-chloro-6-methoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=CC=CC(Cl)=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@H](C)N)=C1 KWLIBQUJFONRSM-AWEZNQCLSA-N 0.000 claims 1
- FGERINFNQINSMH-AWEZNQCLSA-N (1s)-1-[1-[3-(2-fluoro-6-methoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=CC=CC(F)=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@H](C)N)=C1 FGERINFNQINSMH-AWEZNQCLSA-N 0.000 claims 1
- VPHQMUURAIOPTJ-HNNXBMFYSA-N (1s)-1-[1-[3-(2-methoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=CC=CC=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@H](C)N)=C1 VPHQMUURAIOPTJ-HNNXBMFYSA-N 0.000 claims 1
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- DWWPQNSBCRBVNY-ZDUSSCGKSA-N (1s)-1-[1-[3-(3,5-difluoro-2-methoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=C(F)C=C(F)C=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@H](C)N)=C1 DWWPQNSBCRBVNY-ZDUSSCGKSA-N 0.000 claims 1
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- DOHDMDZZTAULIV-AWEZNQCLSA-N (1s)-1-[1-[3-(5-fluoro-2-methoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=CC=C(F)C=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)[C@H](C)N)=C1 DOHDMDZZTAULIV-AWEZNQCLSA-N 0.000 claims 1
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- CJKRCJXOIXCMQV-UHFFFAOYSA-N 1-[1-(3-phenylphenyl)benzimidazol-5-yl]ethanamine Chemical compound C1=NC2=CC(C(N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1 CJKRCJXOIXCMQV-UHFFFAOYSA-N 0.000 claims 1
- KXHCDIDNBFAURY-UHFFFAOYSA-N 1-[1-[3-(2-fluorophenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound C1=NC2=CC(C(N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1F KXHCDIDNBFAURY-UHFFFAOYSA-N 0.000 claims 1
- VPHQMUURAIOPTJ-UHFFFAOYSA-N 1-[1-[3-(2-methoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=CC=CC=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)C(C)N)=C1 VPHQMUURAIOPTJ-UHFFFAOYSA-N 0.000 claims 1
- XQLLHVNGGCGWOW-UHFFFAOYSA-N 1-[1-[3-(4-fluorophenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound C1=NC2=CC(C(N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=C(F)C=C1 XQLLHVNGGCGWOW-UHFFFAOYSA-N 0.000 claims 1
- DOHDMDZZTAULIV-UHFFFAOYSA-N 1-[1-[3-(5-fluoro-2-methoxyphenyl)phenyl]benzimidazol-5-yl]ethanamine Chemical compound COC1=CC=C(F)C=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)C(C)N)=C1 DOHDMDZZTAULIV-UHFFFAOYSA-N 0.000 claims 1
- AUGQXCMJYAPTJI-UHFFFAOYSA-N 1-[1-[3-[2-(trifluoromethoxy)phenyl]phenyl]benzimidazol-5-yl]ethanamine Chemical compound C1=NC2=CC(C(N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1OC(F)(F)F AUGQXCMJYAPTJI-UHFFFAOYSA-N 0.000 claims 1
- RFGVTOIEYHCKAL-OAHLLOKOSA-N 1-[2-[3-[5-[(1r)-1-aminoethyl]benzimidazol-1-yl]phenyl]phenyl]ethanone Chemical compound C1=NC2=CC([C@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1C(C)=O RFGVTOIEYHCKAL-OAHLLOKOSA-N 0.000 claims 1
- RFGVTOIEYHCKAL-HNNXBMFYSA-N 1-[2-[3-[5-[(1s)-1-aminoethyl]benzimidazol-1-yl]phenyl]phenyl]ethanone Chemical compound C1=NC2=CC([C@@H](N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1C(C)=O RFGVTOIEYHCKAL-HNNXBMFYSA-N 0.000 claims 1
- BNSRXWGMIKNAGW-UHFFFAOYSA-N 2-[3-[5-(1-aminoethyl)benzimidazol-1-yl]phenyl]benzonitrile Chemical compound C1=NC2=CC(C(N)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1C#N BNSRXWGMIKNAGW-UHFFFAOYSA-N 0.000 claims 1
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- 2006-12-04 JP JP2008542778A patent/JP2009518292A/ja not_active Abandoned
- 2006-12-04 DK DK06830303.1T patent/DK1996556T3/da active
- 2006-12-04 EP EP06830303A patent/EP1996556B1/en not_active Not-in-force
-
2008
- 2008-03-06 IL IL189974A patent/IL189974A0/en unknown
- 2008-07-04 NO NO20083045A patent/NO20083045L/no not_active Application Discontinuation
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