JP2007538031A5 - - Google Patents
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- JP2007538031A5 JP2007538031A5 JP2007517059A JP2007517059A JP2007538031A5 JP 2007538031 A5 JP2007538031 A5 JP 2007538031A5 JP 2007517059 A JP2007517059 A JP 2007517059A JP 2007517059 A JP2007517059 A JP 2007517059A JP 2007538031 A5 JP2007538031 A5 JP 2007538031A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- hydrogen
- amino
- ethoxy
- alkylamino
- 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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- 229910052739 hydrogen Inorganic materials 0.000 claims description 115
- 239000001257 hydrogen Substances 0.000 claims description 115
- 150000002431 hydrogen Chemical class 0.000 claims description 72
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 66
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 58
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 54
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims description 50
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 43
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 42
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 42
- 229910052736 halogen Inorganic materials 0.000 claims description 39
- 150000002367 halogens Chemical group 0.000 claims description 39
- 125000000623 heterocyclic group Chemical group 0.000 claims description 38
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 38
- -1 benzyloxy, ethoxy, n-propoxy Chemical group 0.000 claims description 37
- 239000012453 solvate Substances 0.000 claims description 34
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 33
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 32
- 125000003282 alkyl amino group Chemical group 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 28
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 23
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 20
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 14
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 13
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 15
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 12
- 125000004432 carbon atom Chemical group C* 0.000 claims 12
- 229910052801 chlorine Inorganic materials 0.000 claims 12
- 239000000460 chlorine Substances 0.000 claims 12
- 229910052731 fluorine Inorganic materials 0.000 claims 12
- 239000011737 fluorine Substances 0.000 claims 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 8
- 229910052794 bromium Inorganic materials 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 4
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000002883 imidazolyl group Chemical group 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 4
- 125000001425 triazolyl group Chemical group 0.000 claims 4
- 208000023275 Autoimmune disease Diseases 0.000 claims 3
- 230000003463 hyperproliferative effect Effects 0.000 claims 3
- 239000012442 inert solvent Substances 0.000 claims 3
- 208000027866 inflammatory disease Diseases 0.000 claims 3
- 230000002757 inflammatory effect Effects 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 230000004770 neurodegeneration Effects 0.000 claims 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims 3
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 238000007796 conventional method Methods 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 1
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 1
- 239000002841 Lewis acid Substances 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- 238000005903 acid hydrolysis reaction Methods 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 229960001716 benzalkonium Drugs 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 150000007517 lewis acids Chemical class 0.000 claims 1
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 claims 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 1
- GHPODDMCSOYWNE-UHFFFAOYSA-N Cc(cc1)cc2c1OCO2 Chemical compound Cc(cc1)cc2c1OCO2 GHPODDMCSOYWNE-UHFFFAOYSA-N 0.000 description 15
- 0 C*1C=CC(C(C(C2*)C3=CC=C*(*)C=C3)(C3(*)[C@]2(*)I=*)Oc2c3c(*)cc(C)c2)=CCC1N* Chemical compound C*1C=CC(C(C(C2*)C3=CC=C*(*)C=C3)(C3(*)[C@]2(*)I=*)Oc2c3c(*)cc(C)c2)=CCC1N* 0.000 description 6
- 150000001721 carbon Chemical group 0.000 description 2
- JHUBNQSPUZXGKI-UHFFFAOYSA-N CC(C)c(cc1)cc2c1OCO2 Chemical compound CC(C)c(cc1)cc2c1OCO2 JHUBNQSPUZXGKI-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004024504A DE102004024504A1 (de) | 2004-05-18 | 2004-05-18 | Neue Cylopenta[b]benzofuran-Derivate und ihre Verwendung |
| PCT/EP2005/005298 WO2005113529A2 (de) | 2004-05-18 | 2005-05-14 | Neue cylopenta[b]benzofuran-derivate und ihre verwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007538031A JP2007538031A (ja) | 2007-12-27 |
| JP2007538031A5 true JP2007538031A5 (https=) | 2011-12-08 |
Family
ID=35207782
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007517059A Pending JP2007538031A (ja) | 2004-05-18 | 2005-05-14 | 新規なシクロペンタ［ｂ］ベンゾフラン誘導体およびその使用 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US8030347B2 (https=) |
| EP (1) | EP1751127B1 (https=) |
| JP (1) | JP2007538031A (https=) |
| KR (1) | KR101215164B1 (https=) |
| CN (1) | CN1989122B (https=) |
| AU (1) | AU2005245104B2 (https=) |
| BR (1) | BRPI0510403A (https=) |
| CA (1) | CA2567404C (https=) |
| DE (1) | DE102004024504A1 (https=) |
| IL (1) | IL179257A (https=) |
| MX (1) | MXPA06013182A (https=) |
| RU (1) | RU2415847C9 (https=) |
| WO (1) | WO2005113529A2 (https=) |
| ZA (1) | ZA200609444B (https=) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1771169A1 (en) | 2004-07-14 | 2007-04-11 | PTC Therapeutics, Inc. | Methods for treating hepatitis c |
| US7781478B2 (en) | 2004-07-14 | 2010-08-24 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| EP1693059A1 (en) * | 2005-02-22 | 2006-08-23 | Deutsches Krebsforschungszentrum | Use of rocaglamide derivatives as NF-AT-specific inhibitors for the treatment of certain inflammatory diseases |
| EP2189453A1 (en) * | 2008-11-25 | 2010-05-26 | Université Louis Pasteur | Rocaglaol derivatives as cardioprotectant agents |
| EP2457907A1 (en) * | 2010-11-16 | 2012-05-30 | Université de Strasbourg | Flavagline derivatives as neuroprotective agents |
| US20140255432A1 (en) * | 2011-07-27 | 2014-09-11 | Ohio State Innovation Foundation | Silvestrol, silvestrol analogs and uses thereof |
| FR3023290B1 (fr) * | 2014-07-04 | 2016-08-19 | Pf Medicament | Derives de flavaglines |
| EP3888658B1 (en) | 2015-11-25 | 2023-12-27 | Effector Therapeutics, Inc. | Eif4-a-inhibiting compounds and methods related thereto |
| EP3755693B1 (en) | 2018-02-19 | 2024-06-12 | Memorial Sloan-Kettering Cancer Center | Agents and methods for treating dysproliferative diseases |
| EP3639820A1 (en) | 2018-10-16 | 2020-04-22 | Universitätsmedizin der Johannes Gutenberg-Universität Mainz | Flavagline derivatives for inhibition of kras oncogene activation |
| CN110646616B (zh) * | 2019-09-05 | 2023-05-30 | 桂林理工大学 | 一种检测血清中人cTnI的超敏荧光猝灭免疫传感器及检测方法 |
| CN110776486B (zh) * | 2019-10-23 | 2022-05-20 | 中国药科大学 | 一种苯并呋喃类小分子p2y14受体抑制剂，及其制备和应用 |
| CA3230542A1 (en) | 2021-09-01 | 2023-03-09 | Krishnaraj Rajalingam | Novel ras inhibitors |
| CN116077483A (zh) * | 2021-11-05 | 2023-05-09 | 上海中医药大学 | 楝酰胺及其类似物的药物用途 |
| CN115385924B (zh) * | 2022-10-06 | 2023-10-13 | 贵州省中国科学院天然产物化学重点实验室(贵州医科大学天然产物化学重点实验室) | 一种具有抗肿瘤活性的环戊烷苯并呋喃类化合物及其应用 |
| WO2024175662A1 (en) | 2023-02-23 | 2024-08-29 | KHR Biotec GmbH | Flavagline derivatives as ras inhibitors |
| JP2026508161A (ja) | 2023-02-23 | 2026-03-10 | エスジェーピー バイオテック ゲーエムベーハー | 新規ＲＡＳ阻害剤３ａＨ－シクロペンタ［ｂ］ベンゾフラン－３ａ－イル |
| WO2025092976A1 (zh) * | 2023-11-03 | 2025-05-08 | 映恩生物制药（苏州）有限公司 | 蛋白翻译抑制剂 |
| TW202545938A (zh) * | 2024-01-16 | 2025-12-01 | 大陸商映恩生物製藥（蘇州）有限公司 | 一種蛋白轉譯抑制劑的偶聯物及其用途 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU191264B (en) * | 1984-01-13 | 1987-01-28 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt,Hu | Process for production of derivatives of 7-oxo-prostacyclin with selective biological effect |
| KR100381584B1 (ko) * | 1994-07-22 | 2003-08-21 | 알타나 파마 아게 | 디히드로벤조푸란 |
| DE19934952A1 (de) * | 1998-07-30 | 2000-02-03 | Novartis Ag | Cyclopentabenzofuran-Derivate |
| DE19835325A1 (de) * | 1998-08-05 | 2000-02-10 | Bayer Ag | Verwendung von Cyclopentabenzofuran-Derivaten zur Bekämpfung von NF-kB abhängigen Krankheiten |
| DE19835324A1 (de) * | 1998-08-05 | 2000-02-10 | Bayer Ag | Cyclopentabenzofuran-Derivate und ihre Verwendung |
| DE10158561A1 (de) * | 2001-11-29 | 2003-06-12 | Bayer Ag | Neue Verwendung von Cyclopentabenzofuranen |
-
2004
- 2004-05-18 DE DE102004024504A patent/DE102004024504A1/de not_active Withdrawn
-
2005
- 2005-05-14 US US11/596,907 patent/US8030347B2/en not_active Expired - Fee Related
- 2005-05-14 EP EP05747405A patent/EP1751127B1/de not_active Expired - Lifetime
- 2005-05-14 BR BRPI0510403-3A patent/BRPI0510403A/pt not_active IP Right Cessation
- 2005-05-14 JP JP2007517059A patent/JP2007538031A/ja active Pending
- 2005-05-14 CN CN2005800241153A patent/CN1989122B/zh not_active Expired - Fee Related
- 2005-05-14 CA CA2567404A patent/CA2567404C/en not_active Expired - Fee Related
- 2005-05-14 MX MXPA06013182A patent/MXPA06013182A/es active IP Right Grant
- 2005-05-14 RU RU2006144710/04A patent/RU2415847C9/ru not_active IP Right Cessation
- 2005-05-14 AU AU2005245104A patent/AU2005245104B2/en not_active Ceased
- 2005-05-14 WO PCT/EP2005/005298 patent/WO2005113529A2/de not_active Ceased
-
2006
- 2006-11-14 IL IL179257A patent/IL179257A/en not_active IP Right Cessation
- 2006-11-14 ZA ZA200609444A patent/ZA200609444B/en unknown
- 2006-11-17 KR KR1020067024170A patent/KR101215164B1/ko not_active Expired - Fee Related