JP2011511806A5 - - Google Patents
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- JP2011511806A5 JP2011511806A5 JP2010546093A JP2010546093A JP2011511806A5 JP 2011511806 A5 JP2011511806 A5 JP 2011511806A5 JP 2010546093 A JP2010546093 A JP 2010546093A JP 2010546093 A JP2010546093 A JP 2010546093A JP 2011511806 A5 JP2011511806 A5 JP 2011511806A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- optionally substituted
- moiety
- atoms
- haloalkoxy
- 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.)
- Ceased
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- 125000000217 alkyl group Chemical group 0.000 claims 76
- 125000004429 atom Chemical group 0.000 claims 29
- 125000003118 aryl group Chemical group 0.000 claims 24
- 125000001072 heteroaryl group Chemical group 0.000 claims 22
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 20
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 20
- 125000003545 alkoxy group Chemical group 0.000 claims 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 20
- 239000008194 pharmaceutical composition Substances 0.000 claims 19
- 125000001475 halogen functional group Chemical group 0.000 claims 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims 14
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 11
- 239000003937 drug carrier Substances 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- 125000004043 oxo group Chemical group O=* 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 125000001188 haloalkyl group Chemical group 0.000 claims 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 210000003027 ear inner Anatomy 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- LBMUGOKSTFDDNF-UHFFFAOYSA-N 1-[2-(4-methoxyphenyl)-1-phenylethyl]benzimidazole Chemical compound COC1=CC=C(C=C1)CC(C1=CC=CC=C1)N1C=NC2=C1C=CC=C2 LBMUGOKSTFDDNF-UHFFFAOYSA-N 0.000 claims 1
- ZQMZRHDICAIAPU-UHFFFAOYSA-N 2,5-dichloro-n-[(1-methylbenzimidazol-2-yl)methyl]aniline Chemical compound N=1C2=CC=CC=C2N(C)C=1CNC1=CC(Cl)=CC=C1Cl ZQMZRHDICAIAPU-UHFFFAOYSA-N 0.000 claims 1
- MAXQKPNEYWTEHI-UHFFFAOYSA-N 2-(phenylsulfanylmethyl)-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1CSC1=CC=CC=C1 MAXQKPNEYWTEHI-UHFFFAOYSA-N 0.000 claims 1
- MWKOUPJMMYDGLH-UHFFFAOYSA-N 2-[(2-methoxyphenoxy)methyl]-1H-benzimidazole Chemical compound COC1=CC=CC=C1OCC1=NC2=CC=CC=C2N1 MWKOUPJMMYDGLH-UHFFFAOYSA-N 0.000 claims 1
- BNZRNEVZOMLBKN-UHFFFAOYSA-N 2-[(2-methylphenoxy)methyl]-1h-benzimidazole Chemical compound CC1=CC=CC=C1OCC1=NC2=CC=CC=C2N1 BNZRNEVZOMLBKN-UHFFFAOYSA-N 0.000 claims 1
- UELQPMYVOWTTFY-UHFFFAOYSA-N 2-[(4-fluorophenoxy)methyl]-1-methylbenzimidazole Chemical compound N=1C2=CC=CC=C2N(C)C=1COC1=CC=C(F)C=C1 UELQPMYVOWTTFY-UHFFFAOYSA-N 0.000 claims 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- RMHDNTKNCCMULG-UHFFFAOYSA-N 3-(6-methyl-1h-benzimidazol-2-yl)chromen-2-imine Chemical compound C1=CC=C2OC(=N)C(C3=NC4=CC=C(C=C4N3)C)=CC2=C1 RMHDNTKNCCMULG-UHFFFAOYSA-N 0.000 claims 1
- UYYUYDDKLNGZQL-UHFFFAOYSA-N 4-[2-(1-methyl-2-benzimidazolyl)ethyl]aniline Chemical compound N=1C2=CC=CC=C2N(C)C=1CCC1=CC=C(N)C=C1 UYYUYDDKLNGZQL-UHFFFAOYSA-N 0.000 claims 1
- KDIBYEXYKOOOBI-UHFFFAOYSA-N 6-chloro-1-[(2-chlorophenyl)methoxy]-2-(4-methoxyphenyl)benzimidazole Chemical compound C1=CC(OC)=CC=C1C1=NC2=CC=C(Cl)C=C2N1OCC1=CC=CC=C1Cl KDIBYEXYKOOOBI-UHFFFAOYSA-N 0.000 claims 1
- VZQOMOTXZJPWTG-UHFFFAOYSA-N 6-chloro-1-[(2-chlorophenyl)methoxy]-2-phenylbenzimidazole Chemical compound C=1C=CC=C(Cl)C=1CON1C2=CC(Cl)=CC=C2N=C1C1=CC=CC=C1 VZQOMOTXZJPWTG-UHFFFAOYSA-N 0.000 claims 1
- GGIZNSCZQDNNIP-UHFFFAOYSA-N 6-chloro-1-[(3,5-dimethylphenyl)methoxy]-2-(4-methoxyphenyl)benzimidazole Chemical compound C1=CC(OC)=CC=C1C1=NC2=CC=C(Cl)C=C2N1OCC1=CC(C)=CC(C)=C1 GGIZNSCZQDNNIP-UHFFFAOYSA-N 0.000 claims 1
- BFSUBYRXVTYOQI-UHFFFAOYSA-N 6-chloro-2-(4-methoxyphenyl)-1-[(4-methoxyphenyl)methoxy]benzimidazole Chemical compound C1=CC(OC)=CC=C1CON1C2=CC(Cl)=CC=C2N=C1C1=CC=C(OC)C=C1 BFSUBYRXVTYOQI-UHFFFAOYSA-N 0.000 claims 1
- MSHNCNCMADMAGG-UHFFFAOYSA-N 6-chloro-2-(4-methoxyphenyl)-1-[(4-methylphenyl)methoxy]benzimidazole Chemical compound C1=CC(OC)=CC=C1C1=NC2=CC=C(Cl)C=C2N1OCC1=CC=C(C)C=C1 MSHNCNCMADMAGG-UHFFFAOYSA-N 0.000 claims 1
- 208000012639 Balance disease Diseases 0.000 claims 1
- -1 C 1 -C 6 alkoxy Chemical group 0.000 claims 1
- 208000017897 Carcinoma of esophagus Diseases 0.000 claims 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims 1
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 208000016621 Hearing disease Diseases 0.000 claims 1
- 208000012659 Joint disease Diseases 0.000 claims 1
- 229930195725 Mannitol Natural products 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 229960005070 ascorbic acid Drugs 0.000 claims 1
- 235000010323 ascorbic acid Nutrition 0.000 claims 1
- 239000011668 ascorbic acid Substances 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- 230000010261 cell growth Effects 0.000 claims 1
- 230000002490 cerebral effect Effects 0.000 claims 1
- REOGMBVECOGANJ-UHFFFAOYSA-N chembl377740 Chemical compound C1=CC(O)=CC=C1C1=NC2=CC=CC=C2N1 REOGMBVECOGANJ-UHFFFAOYSA-N 0.000 claims 1
- 210000003477 cochlea Anatomy 0.000 claims 1
- 210000000860 cochlear nerve Anatomy 0.000 claims 1
- 210000001072 colon Anatomy 0.000 claims 1
- 230000007812 deficiency Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 210000000959 ear middle Anatomy 0.000 claims 1
- 210000000232 gallbladder Anatomy 0.000 claims 1
- 239000008187 granular material Substances 0.000 claims 1
- 210000002266 hair cells auditory Anatomy 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 210000002429 large intestine Anatomy 0.000 claims 1
- 239000002502 liposome Substances 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 239000000594 mannitol Substances 0.000 claims 1
- 235000010355 mannitol Nutrition 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 210000002569 neuron Anatomy 0.000 claims 1
- 210000004798 organs belonging to the digestive system Anatomy 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 210000000496 pancreas Anatomy 0.000 claims 1
- 150000003904 phospholipids Chemical class 0.000 claims 1
- 229920001184 polypeptide Polymers 0.000 claims 1
- 102000004196 processed proteins & peptides Human genes 0.000 claims 1
- 108090000765 processed proteins & peptides Proteins 0.000 claims 1
- 210000000664 rectum Anatomy 0.000 claims 1
- 210000001079 scala tympani Anatomy 0.000 claims 1
- 210000000813 small intestine Anatomy 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 239000000600 sorbitol Substances 0.000 claims 1
- 210000002784 stomach Anatomy 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 0 *c1nc(c(*=C)c(*)c(*)c2*)c2[n]1* Chemical compound *c1nc(c(*=C)c(*)c(*)c2*)c2[n]1* 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2703208P | 2008-02-07 | 2008-02-07 | |
| PCT/US2009/033569 WO2009100438A2 (en) | 2008-02-07 | 2009-02-09 | Compounds that enhance atoh-1 expression |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014087579A Division JP5749829B2 (ja) | 2008-02-07 | 2014-04-21 | Ａｔｏｈ１発現を増強する化合物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011511806A JP2011511806A (ja) | 2011-04-14 |
| JP2011511806A5 true JP2011511806A5 (enExample) | 2012-03-29 |
Family
ID=40408118
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010546093A Ceased JP2011511806A (ja) | 2008-02-07 | 2009-02-09 | Ａｔｏｈ１発現を増強する化合物 |
| JP2014087579A Expired - Fee Related JP5749829B2 (ja) | 2008-02-07 | 2014-04-21 | Ａｔｏｈ１発現を増強する化合物 |
| JP2015099316A Expired - Fee Related JP6199340B2 (ja) | 2008-02-07 | 2015-05-14 | Ａｔｏｈ１発現を増強する化合物 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014087579A Expired - Fee Related JP5749829B2 (ja) | 2008-02-07 | 2014-04-21 | Ａｔｏｈ１発現を増強する化合物 |
| JP2015099316A Expired - Fee Related JP6199340B2 (ja) | 2008-02-07 | 2015-05-14 | Ａｔｏｈ１発現を増強する化合物 |
Country Status (7)
| Country | Link |
|---|---|
| US (5) | US8188131B2 (enExample) |
| EP (2) | EP2732819B1 (enExample) |
| JP (3) | JP2011511806A (enExample) |
| CN (1) | CN101990433B (enExample) |
| AU (1) | AU2009212135B2 (enExample) |
| CA (1) | CA2714370C (enExample) |
| WO (1) | WO2009100438A2 (enExample) |
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| JP2010509919A (ja) | 2006-11-15 | 2010-04-02 | マサチューセッツ・アイ・アンド・イア・インファーマリー | 内耳細胞の生成 |
| ES2542849T3 (es) * | 2007-08-13 | 2015-08-12 | Monsanto Technology Llc | Composiciones y procedimientos de control de nematodos |
| AU2009212135B2 (en) | 2008-02-07 | 2014-08-21 | Massachusetts Eye & Ear Infirmary | Compounds that enhance Atoh-1 expression |
| EP3587413A1 (en) | 2009-02-10 | 2020-01-01 | Monsanto Technology LLC | Compositions and methods for controlling nematodes comprising oxadiazoles |
| US20100222381A1 (en) * | 2009-02-27 | 2010-09-02 | Hariprasad Vankayalapati | Cyclopentathiophene/cyclohexathiophene DNA methyltransferase inhibitors |
| EP2518066B1 (en) | 2009-12-18 | 2016-05-18 | Mitsubishi Tanabe Pharma Corporation | Novel anti-platelet agent |
| CA2829790C (en) | 2010-03-30 | 2018-06-05 | Verseon Corporation | Multisubstituted aromatic compounds as inhibitors of thrombin |
| JP5973996B2 (ja) | 2010-05-26 | 2016-08-23 | カッパーアールエヌエー，インコーポレイテッド | Ａｔｏｈ１に対する天然アンチセンス転写物の阻害による無調ホモログ１（ａｔｏｈ１）関連疾患の治療 |
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-
2009
- 2009-02-09 AU AU2009212135A patent/AU2009212135B2/en not_active Ceased
- 2009-02-09 EP EP13182379.1A patent/EP2732819B1/en active Active
- 2009-02-09 JP JP2010546093A patent/JP2011511806A/ja not_active Ceased
- 2009-02-09 EP EP09708566.6A patent/EP2254572B1/en not_active Not-in-force
- 2009-02-09 US US12/368,173 patent/US8188131B2/en not_active Expired - Fee Related
- 2009-02-09 CA CA2714370A patent/CA2714370C/en active Active
- 2009-02-09 WO PCT/US2009/033569 patent/WO2009100438A2/en not_active Ceased
- 2009-02-09 CN CN200980112358.0A patent/CN101990433B/zh not_active Expired - Fee Related
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2012
- 2012-04-24 US US13/454,702 patent/US8859597B2/en active Active
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2014
- 2014-04-21 JP JP2014087579A patent/JP5749829B2/ja not_active Expired - Fee Related
- 2014-10-10 US US14/511,911 patent/US9433610B2/en not_active Expired - Fee Related
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2015
- 2015-05-14 JP JP2015099316A patent/JP6199340B2/ja not_active Expired - Fee Related
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