JP2012514577A5 - - Google Patents
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- JP2012514577A5 JP2012514577A5 JP2011542926A JP2011542926A JP2012514577A5 JP 2012514577 A5 JP2012514577 A5 JP 2012514577A5 JP 2011542926 A JP2011542926 A JP 2011542926A JP 2011542926 A JP2011542926 A JP 2011542926A JP 2012514577 A5 JP2012514577 A5 JP 2012514577A5
- Authority
- JP
- Japan
- Prior art keywords
- vinyl
- methoxyphenyl
- benzimidazol
- nicotinonitrile
- cyclopentyloxy
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 38
- 125000001188 haloalkyl group Chemical group 0.000 claims description 32
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 31
- -1 nitro, cyano, amino Chemical group 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 27
- 150000002431 hydrogen Chemical class 0.000 claims description 24
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 22
- 208000002193 Pain Diseases 0.000 claims description 18
- 229920002554 vinyl polymer Polymers 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 14
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 13
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 208000004296 neuralgia Diseases 0.000 claims description 7
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 208000035475 disorder Diseases 0.000 claims description 5
- 208000021722 neuropathic pain Diseases 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 208000011580 syndromic disease Diseases 0.000 claims description 5
- 102000011040 TRPV Cation Channels Human genes 0.000 claims description 4
- 108010062740 TRPV Cation Channels Proteins 0.000 claims description 4
- 102000003568 TRPV3 Human genes 0.000 claims description 4
- 101150043371 Trpv3 gene Proteins 0.000 claims description 4
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 4
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 201000008482 osteoarthritis Diseases 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 208000000094 Chronic Pain Diseases 0.000 claims description 3
- 206010020751 Hypersensitivity Diseases 0.000 claims description 3
- 206010061218 Inflammation Diseases 0.000 claims description 3
- 208000004550 Postoperative Pain Diseases 0.000 claims description 3
- 208000005298 acute pain Diseases 0.000 claims description 3
- 208000026935 allergic disease Diseases 0.000 claims description 3
- 230000009610 hypersensitivity Effects 0.000 claims description 3
- 230000004054 inflammatory process Effects 0.000 claims description 3
- 230000001404 mediated effect Effects 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- ZKUCZXBLIXXNJY-CCEZHUSRSA-N 1-(3,5-dichloropyridin-2-yl)-2-[(e)-2-(3-methoxy-2-phenylmethoxyphenyl)ethenyl]benzimidazole Chemical compound C=1C=CC=CC=1COC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC=CC=C2N1C1=NC=C(Cl)C=C1Cl ZKUCZXBLIXXNJY-CCEZHUSRSA-N 0.000 claims description 2
- WEGMRFXNGXTXEE-BUHFOSPRSA-N 1-(3,5-dichloropyridin-2-yl)-2-[(e)-2-[2-[(2-fluorophenyl)methoxy]-3-methoxyphenyl]ethenyl]benzimidazole Chemical compound C=1C=CC=C(F)C=1COC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC=CC=C2N1C1=NC=C(Cl)C=C1Cl WEGMRFXNGXTXEE-BUHFOSPRSA-N 0.000 claims description 2
- ZHMQXIIRTZJNIL-BUHFOSPRSA-N 1-(5-bromopyrimidin-2-yl)-2-[(e)-2-(2-cyclopentyloxy-3-methoxyphenyl)ethenyl]benzimidazole Chemical compound C1CCCC1OC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC=CC=C2N1C1=NC=C(Br)C=N1 ZHMQXIIRTZJNIL-BUHFOSPRSA-N 0.000 claims description 2
- PEYRJXXPTWIGCG-BUHFOSPRSA-N 1-(5-bromopyrimidin-2-yl)-2-[(e)-2-(3-methoxy-2-pentan-3-yloxyphenyl)ethenyl]benzimidazole Chemical compound CCC(CC)OC1=C(OC)C=CC=C1\C=C\C1=NC2=CC=CC=C2N1C1=NC=C(Br)C=N1 PEYRJXXPTWIGCG-BUHFOSPRSA-N 0.000 claims description 2
- WCMHNNLENGLNPZ-FYWRMAATSA-N 1-(5-chloropyridin-2-yl)-2-[(e)-2-(2-cyclopentyloxy-3-methoxyphenyl)ethenyl]benzimidazole Chemical compound C1CCCC1OC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC=CC=C2N1C1=CC=C(Cl)C=N1 WCMHNNLENGLNPZ-FYWRMAATSA-N 0.000 claims description 2
- WWUGKJJZEWTHOR-DYTRJAOYSA-N 1-[(4-tert-butylphenyl)methyl]-2-[(e)-2-(2-cyclopentyloxy-3-methoxyphenyl)ethenyl]benzimidazole Chemical compound C1CCCC1OC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC=CC=C2N1CC1=CC=C(C(C)(C)C)C=C1 WWUGKJJZEWTHOR-DYTRJAOYSA-N 0.000 claims description 2
- UUZRZGQBWFOFPX-BUHFOSPRSA-N 1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-[(e)-2-(2-cyclopentyloxy-3-methoxyphenyl)ethenyl]benzimidazole Chemical compound C1CCCC1OC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC=CC=C2N1C1=NC=C(C(F)(F)F)C=C1Cl UUZRZGQBWFOFPX-BUHFOSPRSA-N 0.000 claims description 2
- XUQUYMXOVKVRCF-WYMLVPIESA-N 2-[(e)-2-(2-butoxy-3-methoxyphenyl)ethenyl]-1-[5-(trifluoromethyl)pyridin-2-yl]benzimidazole Chemical compound CCCCOC1=C(OC)C=CC=C1\C=C\C1=NC2=CC=CC=C2N1C1=CC=C(C(F)(F)F)C=N1 XUQUYMXOVKVRCF-WYMLVPIESA-N 0.000 claims description 2
- SIBXLSQOBJVPFY-VHEBQXMUSA-N 2-[(e)-2-(2-cyclopentyloxy-3-methoxyphenyl)ethenyl]-1-(2-methoxyphenyl)benzimidazole Chemical compound C1CCCC1OC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC=CC=C2N1C1=CC=CC=C1OC SIBXLSQOBJVPFY-VHEBQXMUSA-N 0.000 claims description 2
- DZJLDOOUMDZWLM-FYWRMAATSA-N 2-[(e)-2-(2-cyclopentyloxy-3-methoxyphenyl)ethenyl]-1-(5-nitropyridin-2-yl)benzimidazole Chemical compound C1CCCC1OC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC=CC=C2N1C1=CC=C([N+]([O-])=O)C=N1 DZJLDOOUMDZWLM-FYWRMAATSA-N 0.000 claims description 2
- GPYMWSAGRPHQII-FOCLMDBBSA-N 2-[(e)-2-(2-cyclopentyloxy-3-methoxyphenyl)ethenyl]-1-[3-(trifluoromethyl)pyridin-2-yl]benzimidazole Chemical compound C1CCCC1OC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC=CC=C2N1C1=NC=CC=C1C(F)(F)F GPYMWSAGRPHQII-FOCLMDBBSA-N 0.000 claims description 2
- UKZFCCCFMNXQQA-QGOAFFKASA-N 2-[(e)-2-(2-cyclopentyloxy-3-methoxyphenyl)ethenyl]-1-[4-(trifluoromethyl)phenyl]benzimidazole Chemical compound C1CCCC1OC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC=CC=C2N1C1=CC=C(C(F)(F)F)C=C1 UKZFCCCFMNXQQA-QGOAFFKASA-N 0.000 claims description 2
- XPCGUWNIOWJLSV-FYWRMAATSA-N 2-[(e)-2-(2-cyclopentyloxy-3-methoxyphenyl)ethenyl]-1-[5-(trifluoromethyl)pyridin-2-yl]benzimidazole Chemical compound C1CCCC1OC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC=CC=C2N1C1=CC=C(C(F)(F)F)C=N1 XPCGUWNIOWJLSV-FYWRMAATSA-N 0.000 claims description 2
- FFOWRLKRZPRYPS-WUKNDPDISA-N 2-[(e)-2-(2-cyclopentyloxy-3-methoxyphenyl)ethenyl]-1-pyridin-2-ylbenzimidazole Chemical compound C1CCCC1OC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC=CC=C2N1C1=CC=CC=N1 FFOWRLKRZPRYPS-WUKNDPDISA-N 0.000 claims description 2
- CZIRDKXWKGGALY-UKTHLTGXSA-N 2-[(e)-2-(2-cyclopropyloxy-3-methoxyphenyl)ethenyl]-1-[5-(trifluoromethyl)pyridin-2-yl]benzimidazole Chemical compound C1CC1OC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC=CC=C2N1C1=CC=C(C(F)(F)F)C=N1 CZIRDKXWKGGALY-UKTHLTGXSA-N 0.000 claims description 2
- PHOBBWIKHDLQMJ-JQIJEIRASA-N 2-[(e)-2-(3-methoxy-2-phenylmethoxyphenyl)ethenyl]-1-[5-(trifluoromethyl)pyridin-2-yl]benzimidazole Chemical compound C=1C=CC=CC=1COC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC=CC=C2N1C1=CC=C(C(F)(F)F)C=N1 PHOBBWIKHDLQMJ-JQIJEIRASA-N 0.000 claims description 2
- ATSSEUZSAPGALC-ACCUITESSA-N 2-[(e)-2-(3-methoxy-2-propan-2-yloxyphenyl)ethenyl]-1-[5-(trifluoromethyl)pyridin-2-yl]benzimidazole Chemical compound COC1=CC=CC(\C=C\C=2N(C3=CC=CC=C3N=2)C=2N=CC(=CC=2)C(F)(F)F)=C1OC(C)C ATSSEUZSAPGALC-ACCUITESSA-N 0.000 claims description 2
- FLBWNVBBHQZGSO-NTEUORMPSA-N 2-[(e)-2-[2-(cyclobutylmethoxy)-3-(difluoromethoxy)phenyl]ethenyl]-3-[4-(trifluoromethyl)phenyl]imidazo[4,5-b]pyridine Chemical compound C1CCC1COC=1C(OC(F)F)=CC=CC=1\C=C\C1=NC2=CC=CN=C2N1C1=CC=C(C(F)(F)F)C=C1 FLBWNVBBHQZGSO-NTEUORMPSA-N 0.000 claims description 2
- PXIYZYPXPBEGFE-SAPNQHFASA-N 2-[(e)-2-[2-(cyclopropylmethoxy)-3-methoxyphenyl]ethenyl]-1-(4-methylphenyl)benzimidazole Chemical compound C1CC1COC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC=CC=C2N1C1=CC=C(C)C=C1 PXIYZYPXPBEGFE-SAPNQHFASA-N 0.000 claims description 2
- UYBCLOSHNJBFDK-WYMLVPIESA-N 2-[(e)-2-[2-(cyclopropylmethoxy)-3-methoxyphenyl]ethenyl]-1-[(2,4-difluorophenyl)methyl]benzimidazole Chemical compound C1CC1COC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC=CC=C2N1CC1=CC=C(F)C=C1F UYBCLOSHNJBFDK-WYMLVPIESA-N 0.000 claims description 2
- UWGPTCIJEXHVOO-LFIBNONCSA-N 2-[(e)-2-[2-(cyclopropylmethoxy)-3-methoxyphenyl]ethenyl]-1-[4-(trifluoromethyl)phenyl]benzimidazole Chemical compound C1CC1COC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC=CC=C2N1C1=CC=C(C(F)(F)F)C=C1 UWGPTCIJEXHVOO-LFIBNONCSA-N 0.000 claims description 2
- CPEAXHCQSJTUCL-CCEZHUSRSA-N 2-[(e)-2-[2-(cyclopropylmethoxy)-3-methoxyphenyl]ethenyl]-1-pyridin-2-ylbenzimidazole Chemical compound C1CC1COC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC=CC=C2N1C1=CC=CC=N1 CPEAXHCQSJTUCL-CCEZHUSRSA-N 0.000 claims description 2
- SSNVSQPGYNDCOL-VAWYXSNFSA-N 2-[2-[(e)-2-(2-cyclopentyloxy-3-methoxyphenyl)ethenyl]-5,6-difluorobenzimidazol-1-yl]pyridine-3-carbonitrile Chemical compound C1CCCC1OC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC(F)=C(F)C=C2N1C1=NC=CC=C1C#N SSNVSQPGYNDCOL-VAWYXSNFSA-N 0.000 claims description 2
- MVVJKKDMDRLLRT-BUHFOSPRSA-N 2-[2-[(e)-2-(2-cyclopentyloxy-3-methoxyphenyl)ethenyl]benzimidazol-1-yl]-1,3-thiazole Chemical compound C1CCCC1OC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC=CC=C2N1C1=NC=CS1 MVVJKKDMDRLLRT-BUHFOSPRSA-N 0.000 claims description 2
- TVUSGBNLGGIXER-BUHFOSPRSA-N 2-[2-[(e)-2-(2-cyclopentyloxy-3-methoxyphenyl)ethenyl]benzimidazol-1-yl]-1,3-thiazole-5-carbonitrile Chemical compound C1CCCC1OC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC=CC=C2N1C1=NC=C(C#N)S1 TVUSGBNLGGIXER-BUHFOSPRSA-N 0.000 claims description 2
- AAUCKYUSMQPLAJ-CCEZHUSRSA-N 2-[2-[(e)-2-(2-cyclopentyloxy-3-methoxyphenyl)ethenyl]benzimidazol-1-yl]-4-methyl-1,3-thiazole-5-carbonitrile Chemical compound C1CCCC1OC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC=CC=C2N1C1=NC(C)=C(C#N)S1 AAUCKYUSMQPLAJ-CCEZHUSRSA-N 0.000 claims description 2
- KVNUYAMIMNHQGH-FOCLMDBBSA-N 2-[2-[(e)-2-(2-cyclopentyloxy-3-methoxyphenyl)ethenyl]benzimidazol-1-yl]pyridine-3-carbonitrile Chemical compound C1CCCC1OC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC=CC=C2N1C1=NC=CC=C1C#N KVNUYAMIMNHQGH-FOCLMDBBSA-N 0.000 claims description 2
- FKSIRNLIQNNAFJ-FMIVXFBMSA-N 2-[2-[(e)-2-(2-cyclopropyloxy-3-methoxyphenyl)ethenyl]benzimidazol-1-yl]-1,3-thiazole Chemical compound C1CC1OC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC=CC=C2N1C1=NC=CS1 FKSIRNLIQNNAFJ-FMIVXFBMSA-N 0.000 claims description 2
- PQELOUGDVZOGQU-FOCLMDBBSA-N 2-[2-[(e)-2-[2-(cyclopropylmethoxy)-3-methoxyphenyl]ethenyl]benzimidazol-1-yl]-1,3-benzothiazole Chemical compound COC1=CC=CC(\C=C\C=2N(C3=CC=CC=C3N=2)C=2SC3=CC=CC=C3N=2)=C1OCC1CC1 PQELOUGDVZOGQU-FOCLMDBBSA-N 0.000 claims description 2
- CBJLVUKQPBAIGP-WYMLVPIESA-N 3-[2-[(e)-2-[2-(cyclopropylmethoxy)-3-methoxyphenyl]ethenyl]benzimidazol-1-yl]-4-fluorobenzonitrile Chemical compound C1CC1COC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC=CC=C2N1C1=CC(C#N)=CC=C1F CBJLVUKQPBAIGP-WYMLVPIESA-N 0.000 claims description 2
- SJCZUFOHJXSKBP-SAPNQHFASA-N 4-[2-[(e)-2-(2-butoxy-3-methoxyphenyl)ethenyl]benzimidazol-1-yl]benzonitrile Chemical compound CCCCOC1=C(OC)C=CC=C1\C=C\C1=NC2=CC=CC=C2N1C1=CC=C(C#N)C=C1 SJCZUFOHJXSKBP-SAPNQHFASA-N 0.000 claims description 2
- XSMCLNVFHZVJLQ-WYMLVPIESA-N 4-[2-[(e)-2-[2-(cyclopropylmethoxy)-3-methoxyphenyl]ethenyl]benzimidazol-1-yl]-3-fluorobenzonitrile Chemical compound C1CC1COC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC=CC=C2N1C1=CC=C(C#N)C=C1F XSMCLNVFHZVJLQ-WYMLVPIESA-N 0.000 claims description 2
- GCRGTRIWKNIYSZ-ISLYRVAYSA-N 4-[[2-[(e)-2-(2-cyclopentyloxy-3-methoxyphenyl)ethenyl]benzimidazol-1-yl]methyl]benzonitrile Chemical compound C1CCCC1OC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC=CC=C2N1CC1=CC=C(C#N)C=C1 GCRGTRIWKNIYSZ-ISLYRVAYSA-N 0.000 claims description 2
- HPHWHDSOSCZLSF-FOCLMDBBSA-N 4-[[2-[(e)-2-[2-(cyclopropylmethoxy)-3-methoxyphenyl]ethenyl]benzimidazol-1-yl]methyl]benzonitrile Chemical compound C1CC1COC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC=CC=C2N1CC1=CC=C(C#N)C=C1 HPHWHDSOSCZLSF-FOCLMDBBSA-N 0.000 claims description 2
- DZPMHDXVVIEESN-ISLYRVAYSA-N 4-[[2-[(e)-2-[2-[(2-fluorophenyl)methoxy]-3-methoxyphenyl]ethenyl]benzimidazol-1-yl]methyl]benzonitrile Chemical compound C=1C=CC=C(F)C=1COC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC=CC=C2N1CC1=CC=C(C#N)C=C1 DZPMHDXVVIEESN-ISLYRVAYSA-N 0.000 claims description 2
- XEJVVNYJJNTQRF-PKNBQFBNSA-N 6-[2-[(e)-2-(2-butoxy-3-methoxyphenyl)ethenyl]-5,6-difluorobenzimidazol-1-yl]pyridine-3-carbonitrile Chemical compound CCCCOC1=C(OC)C=CC=C1\C=C\C1=NC2=CC(F)=C(F)C=C2N1C1=CC=C(C#N)C=N1 XEJVVNYJJNTQRF-PKNBQFBNSA-N 0.000 claims description 2
- NFLJBVMRVVSPNH-FYWRMAATSA-N 6-[2-[(e)-2-(2-butoxy-3-methoxyphenyl)ethenyl]benzimidazol-1-yl]pyridine-3-carbonitrile Chemical compound CCCCOC1=C(OC)C=CC=C1\C=C\C1=NC2=CC=CC=C2N1C1=CC=C(C#N)C=N1 NFLJBVMRVVSPNH-FYWRMAATSA-N 0.000 claims description 2
- IQTVYDHNLZSCPM-ACCUITESSA-N 6-[2-[(e)-2-(2-butoxy-3-methoxyphenyl)ethenyl]imidazo[4,5-b]pyridin-3-yl]pyridine-3-carbonitrile Chemical compound CCCCOC1=C(OC)C=CC=C1\C=C\C1=NC2=CC=CN=C2N1C1=CC=C(C#N)C=N1 IQTVYDHNLZSCPM-ACCUITESSA-N 0.000 claims description 2
- IYUNFIGNBCHHOT-ZRDIBKRKSA-N 6-[2-[(e)-2-(2-cyclopentyloxy-3-methoxyphenyl)ethenyl]-4,6-difluorobenzimidazol-1-yl]pyridine-3-carbonitrile Chemical compound C1CCCC1OC=1C(OC)=CC=CC=1\C=C\C1=NC2=C(F)C=C(F)C=C2N1C1=CC=C(C#N)C=N1 IYUNFIGNBCHHOT-ZRDIBKRKSA-N 0.000 claims description 2
- XYFKREPOOAFGSQ-PKNBQFBNSA-N 6-[2-[(e)-2-(2-cyclopentyloxy-3-methoxyphenyl)ethenyl]-5,6-difluorobenzimidazol-1-yl]pyridazine-3-carbonitrile Chemical compound C1CCCC1OC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC(F)=C(F)C=C2N1C1=CC=C(C#N)N=N1 XYFKREPOOAFGSQ-PKNBQFBNSA-N 0.000 claims description 2
- NRLURJZJOINKHW-PKNBQFBNSA-N 6-[2-[(e)-2-(2-cyclopentyloxy-3-methoxyphenyl)ethenyl]-5,6-difluorobenzimidazol-1-yl]pyridazine-3-carboxylic acid Chemical compound C1CCCC1OC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC(F)=C(F)C=C2N1C1=CC=C(C(O)=O)N=N1 NRLURJZJOINKHW-PKNBQFBNSA-N 0.000 claims description 2
- ZKLLQRHKRXLWCF-ZRDIBKRKSA-N 6-[2-[(e)-2-(2-cyclopentyloxy-3-methoxyphenyl)ethenyl]-5,6-difluorobenzimidazol-1-yl]pyridine-3-carbonitrile Chemical compound C1CCCC1OC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC(F)=C(F)C=C2N1C1=CC=C(C#N)C=N1 ZKLLQRHKRXLWCF-ZRDIBKRKSA-N 0.000 claims description 2
- FZURKTJVQVVVRD-WYMLVPIESA-N 6-[2-[(e)-2-(2-cyclopentyloxy-3-methoxyphenyl)ethenyl]-5,6-dimethylbenzimidazol-1-yl]pyridine-3-carbonitrile Chemical compound C1CCCC1OC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC(C)=C(C)C=C2N1C1=CC=C(C#N)C=N1 FZURKTJVQVVVRD-WYMLVPIESA-N 0.000 claims description 2
- YSXPXRMAQMZJCT-ZRDIBKRKSA-N 6-[2-[(e)-2-(2-cyclopentyloxy-3-methoxyphenyl)ethenyl]-5,7-difluorobenzimidazol-1-yl]pyridine-3-carbonitrile Chemical compound C1CCCC1OC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC(F)=CC(F)=C2N1C1=CC=C(C#N)C=N1 YSXPXRMAQMZJCT-ZRDIBKRKSA-N 0.000 claims description 2
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- SNMXIKPSRCUZPJ-LFIBNONCSA-N 2-[(e)-2-[2-(cyclobutylmethoxy)-3-(difluoromethoxy)phenyl]ethenyl]-1-[4-(trifluoromethyl)phenyl]benzimidazole Chemical compound C1CCC1COC=1C(OC(F)F)=CC=CC=1\C=C\C1=NC2=CC=CC=C2N1C1=CC=C(C(F)(F)F)C=C1 SNMXIKPSRCUZPJ-LFIBNONCSA-N 0.000 description 1
- TVDCHJYFTLIXHI-ZHACJKMWSA-N 2-[(e)-2-[2-(cyclobutylmethoxy)-3-methoxyphenyl]ethenyl]-1h-imidazo[4,5-b]pyridine Chemical compound COC1=CC=CC(\C=C\C=2NC3=NC=CC=C3N=2)=C1OCC1CCC1 TVDCHJYFTLIXHI-ZHACJKMWSA-N 0.000 description 1
- HUZBZFIKCBVPMU-DTQAZKPQSA-N 4-[2-[(e)-2-[2-(cyclopropylmethoxy)-3-methoxyphenyl]ethenyl]benzimidazol-1-yl]benzonitrile Chemical compound C1CC1COC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC=CC=C2N1C1=CC=C(C#N)C=C1 HUZBZFIKCBVPMU-DTQAZKPQSA-N 0.000 description 1
- CSASCNRGJLQZED-ZRDIBKRKSA-N 6-[2-[(e)-2-(2-cyclopentyloxy-3-methoxyphenyl)ethenyl]imidazo[4,5-c]pyridin-1-yl]pyridine-3-carbonitrile Chemical compound C1CCCC1OC=1C(OC)=CC=CC=1\C=C\C1=NC2=CN=CC=C2N1C1=CC=C(C#N)C=N1 CSASCNRGJLQZED-ZRDIBKRKSA-N 0.000 description 1
- RUBUZRHPXAQCDX-OWBHPGMISA-N 6-[2-[(z)-2-[3-methoxy-2-(2-methylpropoxy)phenyl]ethenyl]benzimidazol-1-yl]pyridine-3-carbonitrile Chemical compound COC1=CC=CC(\C=C/C=2N(C3=CC=CC=C3N=2)C=2N=CC(=CC=2)C#N)=C1OCC(C)C RUBUZRHPXAQCDX-OWBHPGMISA-N 0.000 description 1
- CNTOVOVYPBYAQG-ZRDIBKRKSA-N 6-[4,6-difluoro-2-[(e)-2-(3-methoxy-2-pentoxyphenyl)ethenyl]benzimidazol-1-yl]pyridine-3-carbonitrile Chemical compound CCCCCOC1=C(OC)C=CC=C1\C=C\C1=NC2=C(F)C=C(F)C=C2N1C1=CC=C(C#N)C=N1 CNTOVOVYPBYAQG-ZRDIBKRKSA-N 0.000 description 1
- HZLZNVVIJXTLMF-ZRDIBKRKSA-N 6-[5-chloro-2-[(e)-2-(2-cyclopentyloxy-3-methoxyphenyl)ethenyl]-6-fluorobenzimidazol-1-yl]pyridine-3-carbonitrile Chemical compound C1CCCC1OC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC(Cl)=C(F)C=C2N1C1=CC=C(C#N)C=N1 HZLZNVVIJXTLMF-ZRDIBKRKSA-N 0.000 description 1
- MNAVQURGXCVELW-ZRDIBKRKSA-N 6-[6-chloro-2-[(e)-2-(2-cyclopentyloxy-3-methoxyphenyl)ethenyl]imidazo[4,5-b]pyridin-3-yl]pyridine-3-carbonitrile Chemical compound C1CCCC1OC=1C(OC)=CC=CC=1\C=C\C1=NC2=CC(Cl)=CN=C2N1C1=CC=C(C#N)C=N1 MNAVQURGXCVELW-ZRDIBKRKSA-N 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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| US23743409P | 2009-08-27 | 2009-08-27 | |
| US61/237,434 | 2009-08-27 | ||
| PCT/IB2009/008018 WO2010073128A2 (en) | 2008-12-26 | 2009-12-23 | Fused imidazole derivatives as trpv3 antagonist |
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| EP (1) | EP2370425A4 (enExample) |
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| WO2012129491A1 (en) * | 2011-03-24 | 2012-09-27 | Abbott Laboratories | Trpv3 modulators |
| WO2016023954A2 (en) | 2014-08-12 | 2016-02-18 | Syngenta Participations Ag | Pesticidally active heterocyclic derivatives with sulphur containing substituents |
| CN107735396B (zh) | 2015-07-01 | 2021-03-02 | 先正达参股股份有限公司 | 具有含硫取代基的杀有害生物活性多环衍生物 |
| CN108290885A (zh) | 2015-11-23 | 2018-07-17 | 先正达参股股份有限公司 | 具有含硫和含环丙基的取代基的杀有害生物活性杂环衍生物 |
| CN105503737B (zh) * | 2016-01-25 | 2018-06-19 | 大连理工大学 | 一种无催化剂制备苯并咪唑类或苯并噻唑类化合物的方法 |
| WO2017134066A1 (en) | 2016-02-05 | 2017-08-10 | Syngenta Participations Ag | Pesticidally active heterocyclic derivatives with sulphur containing substituents |
| CN109414430B (zh) * | 2016-06-17 | 2022-11-01 | 药物递送解决方案私人有限责任公司 | 用于治疗尿毒性瘙痒症的制剂 |
| AR118243A1 (es) | 2019-03-07 | 2021-09-22 | Pi Industries Ltd | Compuestos heterocíclicos fusionados y su uso como agentes de control de plagas |
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| JPS625966A (ja) * | 1985-07-03 | 1987-01-12 | Nippon Shinyaku Co Ltd | ベンズイミダゾ−ル誘導体 |
| US20040009537A1 (en) | 2002-01-11 | 2004-01-15 | Jack Roos | Methods of modulating and of identifying agents that modulate intracellular calcium |
| JP4448170B2 (ja) | 2004-08-18 | 2010-04-07 | ベッチャー・ローベルト | エノサル歯科インプラント |
| WO2006065686A2 (en) | 2004-12-13 | 2006-06-22 | Galileo Pharmaceuticals, Inc. | Spiro derivatives as lipoxygenase inhibitors |
| US7842703B2 (en) | 2005-10-07 | 2010-11-30 | Glenmark Pharmaceuticals S.A. | Substituted benzofused derivatives and their use as vanilloid receptor ligands |
| AU2006311883A1 (en) | 2005-11-04 | 2007-05-18 | Hydra Biosciences, Inc. | Compounds for modulating TRPV3 function |
| EP1957486A4 (en) * | 2005-11-23 | 2009-11-11 | Painceptor Pharma Corp | COMPOSITIONS AND METHODS FOR MODULATION OF IONIC CHANNELS |
| WO2008033564A1 (en) | 2006-09-15 | 2008-03-20 | Hydra Biosciences Inc. | Compounds for modulating trpv3 function |
| WO2008140750A1 (en) * | 2007-05-10 | 2008-11-20 | Hydra Biosciences Inc. | Compounds for modulating trpv3 function |
| NZ595776A (en) | 2007-12-18 | 2013-08-30 | Glenmark Pharmaceuticals Sa | Chromane derivatives as trpv3 modulators |
| EP2229388A4 (en) | 2008-01-11 | 2012-03-07 | Glenmark Pharmaceuticals Sa | CONDENSED PYRIMIDINE DERIVATIVES AS TRPV3 MODULATORS |
| US8119647B2 (en) * | 2008-04-23 | 2012-02-21 | Glenmark Pharmaceuticals S.A. | Fused pyrimidineone compounds as TRPV3 modulators |
| US8318928B2 (en) * | 2008-12-15 | 2012-11-27 | Glenmark Pharmaceuticals, S.A. | Fused imidazole carboxamides as TRPV3 modulators |
-
2009
- 2009-12-23 CA CA2744911A patent/CA2744911A1/en not_active Abandoned
- 2009-12-23 MX MX2011006821A patent/MX2011006821A/es active IP Right Grant
- 2009-12-23 NZ NZ595775A patent/NZ595775A/xx not_active IP Right Cessation
- 2009-12-23 JP JP2011542926A patent/JP2012514577A/ja active Pending
- 2009-12-23 AU AU2009332651A patent/AU2009332651A1/en not_active Abandoned
- 2009-12-23 WO PCT/IB2009/008018 patent/WO2010073128A2/en not_active Ceased
- 2009-12-23 US US13/141,199 patent/US8344010B2/en not_active Expired - Fee Related
- 2009-12-23 GE GEAP200912274A patent/GEP20146096B/en unknown
- 2009-12-23 EA EA201190086A patent/EA201190086A1/ru unknown
- 2009-12-23 EP EP09834200A patent/EP2370425A4/en not_active Withdrawn
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