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
Applications Claiming Priority (9)
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|---|---|---|---|
| IN2705/MUM/2008 | 2008-12-26 | ||
| IN2705MU2008 | 2008-12-26 | ||
| US14686509P | 2009-01-23 | 2009-01-23 | |
| US61/146,865 | 2009-01-23 | ||
| IN1732/MUM/2009 | 2009-07-29 | ||
| IN1732MU2009 | 2009-07-29 | ||
| 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 |
Publications (2)
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| JP2012514577A JP2012514577A (ja) | 2012-06-28 |
| JP2012514577A5 true JP2012514577A5 (https=) | 2013-02-14 |
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Country Status (10)
| Country | Link |
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| US (1) | US8344010B2 (https=) |
| EP (1) | EP2370425A4 (https=) |
| JP (1) | JP2012514577A (https=) |
| AU (1) | AU2009332651A1 (https=) |
| CA (1) | CA2744911A1 (https=) |
| EA (1) | EA201190086A1 (https=) |
| GE (1) | GEP20146096B (https=) |
| MX (1) | MX2011006821A (https=) |
| NZ (1) | NZ595775A (https=) |
| WO (1) | WO2010073128A2 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US9012651B2 (en) * | 2011-03-24 | 2015-04-21 | Abbvie Inc. | TRPV3 modulators |
| CN107074846B (zh) | 2014-08-12 | 2020-05-19 | 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杂环衍生物 |
| WO2017001314A1 (en) | 2015-07-01 | 2017-01-05 | Syngenta Participations Ag | Pesticidally active polycyclic derivatives with sulfur containing substituents |
| BR112018010347A2 (pt) | 2015-11-23 | 2018-12-04 | Syngenta Participations Ag | derivados heterocíclicos ativos em termos pesticidas com substituintes contendo enxofre e ciclopropila |
| 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 |
| US12612369B1 (en) | 2025-12-15 | 2026-04-28 | King Faisal University | Eco-friendly synthesis of a novel nicotinonitrile derivative (MNPN) with antibacterial and anti-inflammatory activities for preventing pressure ulcers in individuals with disabilities |
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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 |
| AU2005316739A1 (en) | 2004-12-13 | 2006-06-22 | Galileo Pharmaceuticals, Inc. | Spiro derivatives as lipoxygenase inhibitors |
| JP2009511465A (ja) | 2005-10-07 | 2009-03-19 | グレンマーク・ファーマシューティカルズ・エスエー | 置換ベンゾ縮合誘導体およびバニロイド受容体リガンドとしてのその使用 |
| US7893260B2 (en) | 2005-11-04 | 2011-02-22 | Hydra Biosciences, Inc. | Substituted quinazolin-4-one compounds for antagonizing TRPV3 function |
| WO2007059608A1 (en) * | 2005-11-23 | 2007-05-31 | Painceptor Pharma Corporation | Compositions and methods for modulating gated ion channels |
| US7998980B2 (en) | 2006-09-15 | 2011-08-16 | Hydra Biosciences, Inc. | Compounds for modulating TRPV3 function |
| WO2008140750A1 (en) | 2007-05-10 | 2008-11-20 | Hydra Biosciences Inc. | Compounds for modulating trpv3 function |
| WO2009084034A2 (en) | 2007-12-18 | 2009-07-09 | Glenmark Pharmaceuticals, S. A. | Chromane derivatives as trpv3 modulators |
| CA2724008A1 (en) * | 2008-01-11 | 2009-09-11 | Glenmark Pharmaceuticals, S.A. | Fused 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
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- 2009-12-23 AU AU2009332651A patent/AU2009332651A1/en not_active Abandoned
- 2009-12-23 MX MX2011006821A patent/MX2011006821A/es active IP Right Grant
- 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 WO PCT/IB2009/008018 patent/WO2010073128A2/en not_active Ceased
- 2009-12-23 EP EP09834200A patent/EP2370425A4/en not_active Withdrawn
- 2009-12-23 CA CA2744911A patent/CA2744911A1/en not_active Abandoned
- 2009-12-23 NZ NZ595775A patent/NZ595775A/xx not_active IP Right Cessation
- 2009-12-23 EA EA201190086A patent/EA201190086A1/ru unknown
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