JP2012520238A5 - - Google Patents
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- Publication number
- JP2012520238A5 JP2012520238A5 JP2011538739A JP2011538739A JP2012520238A5 JP 2012520238 A5 JP2012520238 A5 JP 2012520238A5 JP 2011538739 A JP2011538739 A JP 2011538739A JP 2011538739 A JP2011538739 A JP 2011538739A JP 2012520238 A5 JP2012520238 A5 JP 2012520238A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- alkyl
- atom
- ring
- hydrogen atom
- 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 48
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 32
- 150000001875 compounds Chemical class 0.000 claims 27
- 125000001424 substituent group Chemical group 0.000 claims 21
- 125000005843 halogen group Chemical group 0.000 claims 20
- 125000003545 alkoxy group Chemical group 0.000 claims 19
- -1 hydroxy, amino Chemical group 0.000 claims 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 12
- 125000004432 carbon atom Chemical group C* 0.000 claims 9
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 239000003814 drug Substances 0.000 claims 7
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 6
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 6
- 125000003282 alkyl amino group Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims 6
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- 150000004885 piperazines Chemical group 0.000 claims 5
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 239000000651 prodrug Substances 0.000 claims 4
- 229940002612 prodrug Drugs 0.000 claims 4
- 125000003107 substituted aryl group Chemical group 0.000 claims 4
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 3
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical group C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000004434 sulfur atom Chemical group 0.000 claims 3
- 229940124597 therapeutic agent Drugs 0.000 claims 3
- 125000006618 5- to 10-membered aromatic heterocyclic group Chemical group 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 2
- USMYLEIMHJBZIK-UHFFFAOYSA-N [5-[4-(4-methoxyphenyl)piperazin-1-yl]-2,4,6,7-tetramethyl-3h-1-benzofuran-2-yl]methanol Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C(=C(C)C=3OC(C)(CO)CC=3C=2C)C)CC1 USMYLEIMHJBZIK-UHFFFAOYSA-N 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 2
- 208000015114 central nervous system disease Diseases 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 230000003449 preventive effect Effects 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- APUZBYOMJYSTGT-UHFFFAOYSA-N (3-methyl-5-morpholin-4-yl-1-benzofuran-2-yl)methanol Chemical compound C1=C2C(C)=C(CO)OC2=CC=C1N1CCOCC1 APUZBYOMJYSTGT-UHFFFAOYSA-N 0.000 claims 1
- HOLPXUYAXOUELB-UHFFFAOYSA-N (5-piperazin-1-yl-2,3-dihydro-1-benzofuran-2-yl)methanol Chemical compound C=1C=C2OC(CO)CC2=CC=1N1CCNCC1 HOLPXUYAXOUELB-UHFFFAOYSA-N 0.000 claims 1
- CCCWDSKOVIQNOE-UHFFFAOYSA-N (6-fluoro-5-piperazin-1-yl-2,3-dihydro-1-benzofuran-2-yl)methanol Chemical compound FC=1C=C2OC(CO)CC2=CC=1N1CCNCC1 CCCWDSKOVIQNOE-UHFFFAOYSA-N 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- RWBZIVWGBQJMCL-UHFFFAOYSA-N 1-(4-ethoxyphenyl)-4-(7-methoxy-2,2,4,6-tetramethyl-3h-1-benzofuran-5-yl)piperazine Chemical compound C1=CC(OCC)=CC=C1N1CCN(C=2C(=C(OC)C=3OC(C)(C)CC=3C=2C)C)CC1 RWBZIVWGBQJMCL-UHFFFAOYSA-N 0.000 claims 1
- BBLZNCBOMKSSDU-UHFFFAOYSA-N 1-(4-methoxyphenyl)-4-(2,2,4,6,7-pentamethyl-3h-1-benzofuran-5-yl)piperazine Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C(=C(C)C=3OC(C)(C)CC=3C=2C)C)CC1 BBLZNCBOMKSSDU-UHFFFAOYSA-N 0.000 claims 1
- WRPMWTPZEKOJIH-UHFFFAOYSA-N 1-(4-methoxyphenyl)-4-(7-methoxy-2,2,4,6-tetramethyl-3h-1-benzofuran-5-yl)piperazine Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C(=C(OC)C=3OC(C)(C)CC=3C=2C)C)CC1 WRPMWTPZEKOJIH-UHFFFAOYSA-N 0.000 claims 1
- YVBZPAWLIVCPHA-OAHLLOKOSA-N 1-(4-methoxyphenyl)-4-[(2r)-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-5-yl]piperazine Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C(=C(C)C=3O[C@H](C)CC=3C=2C)C)CC1 YVBZPAWLIVCPHA-OAHLLOKOSA-N 0.000 claims 1
- YVBZPAWLIVCPHA-HNNXBMFYSA-N 1-(4-methoxyphenyl)-4-[(2s)-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-5-yl]piperazine Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C(=C(C)C=3O[C@@H](C)CC=3C=2C)C)CC1 YVBZPAWLIVCPHA-HNNXBMFYSA-N 0.000 claims 1
- HXXWQGPFTCUMRG-UHFFFAOYSA-N 1-[2-(methoxymethyl)-2,3-dihydro-1-benzofuran-5-yl]piperazine Chemical compound C=1C=C2OC(COC)CC2=CC=1N1CCNCC1 HXXWQGPFTCUMRG-UHFFFAOYSA-N 0.000 claims 1
- LYIXHSHLRKNUDJ-UHFFFAOYSA-N 1-[6-fluoro-2-(methoxymethyl)-2,3-dihydro-1-benzofuran-5-yl]piperazine Chemical compound FC=1C=C2OC(COC)CC2=CC=1N1CCNCC1 LYIXHSHLRKNUDJ-UHFFFAOYSA-N 0.000 claims 1
- BNHNDMCOCCMSLO-UHFFFAOYSA-N 2-[4-(6-amino-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]acetamide Chemical compound C1CN(CC(=O)N)CCN1C(C(=C1)N)=CC2=C1OCC2 BNHNDMCOCCMSLO-UHFFFAOYSA-N 0.000 claims 1
- DUSDRDVPZZFQHC-UHFFFAOYSA-N 3-[[4-[[cyclohexyl-(3-methyl-5-morpholin-4-yl-1-benzofuran-2-yl)methyl]amino]benzoyl]-methylamino]propanoic acid Chemical compound C1=CC(C(=O)N(CCC(O)=O)C)=CC=C1NC(C1=C(C2=CC(=CC=C2O1)N1CCOCC1)C)C1CCCCC1 DUSDRDVPZZFQHC-UHFFFAOYSA-N 0.000 claims 1
- VGOCTMNMAFRJJN-UHFFFAOYSA-N 4-(2,3,4,7-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)morpholine Chemical compound CC1C(C)OC(C(=C2)C)=C1C(C)=C2N1CCOCC1 VGOCTMNMAFRJJN-UHFFFAOYSA-N 0.000 claims 1
- 108090000723 Insulin-Like Growth Factor I Proteins 0.000 claims 1
- 102000004218 Insulin-Like Growth Factor I Human genes 0.000 claims 1
- 108091008611 Protein Kinase B Proteins 0.000 claims 1
- 102000005765 Proto-Oncogene Proteins c-akt Human genes 0.000 claims 1
- 239000012190 activator Substances 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- JNZOEWQIUBLZQU-UHFFFAOYSA-N cyclohexyl-(3-methyl-5-morpholin-4-yl-1-benzofuran-2-yl)methanol Chemical compound C1=C2C(C)=C(C(O)C3CCCCC3)OC2=CC=C1N1CCOCC1 JNZOEWQIUBLZQU-UHFFFAOYSA-N 0.000 claims 1
- RKTGGAKUVNUVGY-UHFFFAOYSA-N ethyl 3-[[4-[[cyclohexyl-(3-methyl-5-morpholin-4-yl-1-benzofuran-2-yl)methyl]amino]benzoyl]-methylamino]propanoate Chemical compound C1=CC(C(=O)N(C)CCC(=O)OCC)=CC=C1NC(C1=C(C2=CC(=CC=C2O1)N1CCOCC1)C)C1CCCCC1 RKTGGAKUVNUVGY-UHFFFAOYSA-N 0.000 claims 1
- 150000004050 homopiperazines Chemical group 0.000 claims 1
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 230000000069 prophylactic effect Effects 0.000 claims 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2011538739A JP5746631B2 (ja) | 2009-03-10 | 2010-03-09 | ベンゾフラン誘導体 |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2009056719 | 2009-03-10 | ||
| JP2009056719 | 2009-03-10 | ||
| JP2011538739A JP5746631B2 (ja) | 2009-03-10 | 2010-03-09 | ベンゾフラン誘導体 |
| PCT/JP2010/054286 WO2010104194A1 (en) | 2009-03-10 | 2010-03-09 | Benzofuran derivatives |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014226377A Division JP5841651B2 (ja) | 2009-03-10 | 2014-11-06 | ベンゾフラン誘導体 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012520238A JP2012520238A (ja) | 2012-09-06 |
| JP2012520238A5 true JP2012520238A5 (enExample) | 2013-04-18 |
| JP5746631B2 JP5746631B2 (ja) | 2015-07-08 |
Family
ID=42224778
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011538739A Expired - Fee Related JP5746631B2 (ja) | 2009-03-10 | 2010-03-09 | ベンゾフラン誘導体 |
| JP2014226377A Expired - Fee Related JP5841651B2 (ja) | 2009-03-10 | 2014-11-06 | ベンゾフラン誘導体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014226377A Expired - Fee Related JP5841651B2 (ja) | 2009-03-10 | 2014-11-06 | ベンゾフラン誘導体 |
Country Status (37)
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8288390B2 (en) * | 2009-03-10 | 2012-10-16 | Takeda Pharmaceutical Company Limited | Benzofuran derivatives |
| EP2502909A4 (en) | 2009-11-18 | 2013-04-03 | Takeda Pharmaceutical | aminopyridine derivative |
| EP2817353B1 (en) | 2012-02-20 | 2021-01-13 | Basf Se | Enhancing the antimicrobial activity of biocides with polymers |
| US9908680B2 (en) | 2012-09-28 | 2018-03-06 | Kimberly-Clark Worldwide, Inc. | Tree-free fiber compositions and uses in containerboard packaging |
| US9816233B2 (en) * | 2012-09-28 | 2017-11-14 | Kimberly-Clark Worldwide, Inc. | Hybrid fiber compositions and uses in containerboard packaging |
| EP2903980B1 (en) * | 2012-10-01 | 2017-07-19 | F. Hoffmann-La Roche AG | Benzimidazoles as cns active agents |
| KR101716099B1 (ko) * | 2013-09-12 | 2017-03-13 | 에프. 호프만-라 로슈 아게 | 인돌-카복스아마이드 유도체 |
| CN110770211B (zh) | 2017-06-23 | 2023-09-19 | 协和麒麟株式会社 | α,β不饱和酰胺化合物 |
| CN109580790A (zh) * | 2017-09-28 | 2019-04-05 | 安徽省庆云医药股份有限公司 | 一种液相色谱法分离测定西洛多辛及其光学异构体的方法 |
| CN108530405A (zh) * | 2018-05-08 | 2018-09-14 | 南京晓庄学院 | 非金属路易斯酸催化烯烃分子内加成c-o键合成苯并呋喃衍生物的方法 |
| CN109879839B (zh) * | 2019-03-12 | 2023-04-25 | 沈阳大学 | 6-哌嗪甲基-7-羟基苯并呋喃类化合物及其医药用途 |
| CN113045523B (zh) * | 2019-12-27 | 2022-09-23 | 上海泓博智源医药股份有限公司 | 一种咪唑啉吡啶化合物中间体的制备方法 |
| TWI894229B (zh) * | 2020-03-16 | 2025-08-21 | 瑞士商諾華公司 | 作為yap/taz-tead蛋白-蛋白相互作用抑制劑之聯芳基衍生物 |
| CN111362965B (zh) * | 2020-04-27 | 2022-05-03 | 梯尔希（南京）药物研发有限公司 | 一种莫西菌素杂质的制备方法 |
| CN113219085B (zh) * | 2021-03-31 | 2022-05-13 | 河北国龙制药有限公司 | 一种2,3-二甲基溴苯有关物质的检测方法 |
| CN113214205B (zh) * | 2021-04-09 | 2022-06-10 | 南方海洋科学与工程广东省实验室(湛江) | 一种色原酮衍生物的制备方法 |
| CN115260136B (zh) * | 2022-08-09 | 2023-08-15 | 嘉兴学院 | 一种苯酞类化合物及其制备方法 |
| CN115724721A (zh) * | 2022-12-19 | 2023-03-03 | 山东京博石油化工有限公司 | 一种2-取代基-4-溴苯酚的制备方法 |
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-
2010
- 2010-03-09 US US12/659,447 patent/US8288390B2/en not_active Expired - Fee Related
- 2010-03-09 WO PCT/JP2010/054286 patent/WO2010104194A1/en not_active Ceased
- 2010-03-09 EP EP10710111.5A patent/EP2406243B1/en active Active
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