JP2009517401A5 - - Google Patents
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- Publication number
- JP2009517401A5 JP2009517401A5 JP2008542528A JP2008542528A JP2009517401A5 JP 2009517401 A5 JP2009517401 A5 JP 2009517401A5 JP 2008542528 A JP2008542528 A JP 2008542528A JP 2008542528 A JP2008542528 A JP 2008542528A JP 2009517401 A5 JP2009517401 A5 JP 2009517401A5
- Authority
- JP
- Japan
- Prior art keywords
- butyl
- methyl
- chloro
- aldehyde
- bromo
- 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
Links
- -1 carboxyethyl Chemical group 0.000 claims 129
- 125000001309 chloro group Chemical group Cl* 0.000 claims 37
- 150000001299 aldehydes Chemical class 0.000 claims 35
- 125000001246 bromo group Chemical group Br* 0.000 claims 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 35
- 125000000217 alkyl group Chemical group 0.000 claims 34
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 33
- 125000005843 halogen group Chemical group 0.000 claims 33
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 33
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 33
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 33
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 33
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 33
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 33
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 33
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 33
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 33
- 239000008194 pharmaceutical composition Substances 0.000 claims 32
- 150000002148 esters Chemical class 0.000 claims 31
- 229910052739 hydrogen Inorganic materials 0.000 claims 30
- 239000001257 hydrogen Substances 0.000 claims 30
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 30
- 150000002576 ketones Chemical class 0.000 claims 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 6
- 230000000694 effects Effects 0.000 claims 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 6
- 125000000842 isoxazolyl group Chemical group 0.000 claims 6
- 125000004076 pyridyl group Chemical group 0.000 claims 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 6
- 230000037361 pathway Effects 0.000 claims 5
- 108010014186 ras Proteins Proteins 0.000 claims 5
- 102000016914 ras Proteins Human genes 0.000 claims 5
- LULITKYYLCRIIB-UHFFFAOYSA-N (1-methylindol-3-yl)methanol Chemical compound C1=CC=C2N(C)C=C(CO)C2=C1 LULITKYYLCRIIB-UHFFFAOYSA-N 0.000 claims 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 150000001408 amides Chemical class 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 3
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000002541 furyl group Chemical group 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- 125000001041 indolyl group Chemical group 0.000 claims 3
- 125000000468 ketone group Chemical group 0.000 claims 3
- 125000002971 oxazolyl group Chemical group 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 3
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000000335 thiazolyl group Chemical group 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- 101710113436 GTPase KRas Proteins 0.000 claims 2
- 239000004471 Glycine Substances 0.000 claims 2
- 230000005907 cancer growth Effects 0.000 claims 2
- 230000004640 cellular pathway Effects 0.000 claims 2
- 231100000433 cytotoxic Toxicity 0.000 claims 2
- 230000001472 cytotoxic effect Effects 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 239000000651 prodrug Substances 0.000 claims 2
- 229940002612 prodrug Drugs 0.000 claims 2
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
- 102100033479 RAF proto-oncogene serine/threonine-protein kinase Human genes 0.000 claims 1
- 101710141955 RAF proto-oncogene serine/threonine-protein kinase Proteins 0.000 claims 1
- LPIARNOLFFSUSO-UHFFFAOYSA-N [1-[(3-chlorophenyl)methyl]indol-3-yl]methanol Chemical compound C12=CC=CC=C2C(CO)=CN1CC1=CC=CC(Cl)=C1 LPIARNOLFFSUSO-UHFFFAOYSA-N 0.000 claims 1
- RTMZRUNHLPXWPD-UHFFFAOYSA-N [1-[[3-(trifluoromethyl)phenyl]methyl]indol-3-yl]methanol Chemical compound C12=CC=CC=C2C(CO)=CN1CC1=CC=CC(C(F)(F)F)=C1 RTMZRUNHLPXWPD-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 238000011319 anticancer therapy Methods 0.000 claims 1
- 238000011394 anticancer treatment Methods 0.000 claims 1
- 230000006907 apoptotic process Effects 0.000 claims 1
- 210000004369 blood Anatomy 0.000 claims 1
- 239000008280 blood Substances 0.000 claims 1
- 210000000988 bone and bone Anatomy 0.000 claims 1
- 210000001185 bone marrow Anatomy 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 210000000481 breast Anatomy 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 210000003679 cervix uteri Anatomy 0.000 claims 1
- 238000002512 chemotherapy Methods 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 210000003238 esophagus Anatomy 0.000 claims 1
- 210000001035 gastrointestinal tract Anatomy 0.000 claims 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims 1
- 210000003128 head Anatomy 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 238000009169 immunotherapy Methods 0.000 claims 1
- 230000001939 inductive effect Effects 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- 230000004060 metabolic process Effects 0.000 claims 1
- 239000002207 metabolite Substances 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N methylquinoline Natural products C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 210000001989 nasopharynx Anatomy 0.000 claims 1
- ZDRQMXCSSAPUMM-UHFFFAOYSA-N oncrasin-1 Chemical compound C1=CC(Cl)=CC=C1CN1C2=CC=CC=C2C(C=O)=C1 ZDRQMXCSSAPUMM-UHFFFAOYSA-N 0.000 claims 1
- 210000001672 ovary Anatomy 0.000 claims 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 1
- 210000000496 pancreas Anatomy 0.000 claims 1
- 230000034190 positive regulation of NF-kappaB transcription factor activity Effects 0.000 claims 1
- 210000002307 prostate Anatomy 0.000 claims 1
- 238000001959 radiotherapy Methods 0.000 claims 1
- 210000003491 skin Anatomy 0.000 claims 1
- 210000002784 stomach Anatomy 0.000 claims 1
- 238000001356 surgical procedure Methods 0.000 claims 1
- 210000001550 testis Anatomy 0.000 claims 1
- 230000035897 transcription Effects 0.000 claims 1
- 238000013518 transcription Methods 0.000 claims 1
- 238000011282 treatment Methods 0.000 claims 1
- 210000003932 urinary bladder Anatomy 0.000 claims 1
- 230000029812 viral genome replication Effects 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73986505P | 2005-11-23 | 2005-11-23 | |
| US60/739,865 | 2005-11-23 | ||
| PCT/US2006/061219 WO2007062399A2 (en) | 2005-11-23 | 2006-11-22 | Oncogenic ras-specific cytotoxic compound and methods of use thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009517401A JP2009517401A (ja) | 2009-04-30 |
| JP2009517401A5 true JP2009517401A5 (enExample) | 2010-07-29 |
| JP5460054B2 JP5460054B2 (ja) | 2014-04-02 |
Family
ID=38068056
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008542528A Expired - Fee Related JP5460054B2 (ja) | 2005-11-23 | 2006-11-22 | 腫瘍形成性ｒａｓ特異的細胞障害性化合物およびその使用法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8883841B2 (enExample) |
| EP (1) | EP1956910B1 (enExample) |
| JP (1) | JP5460054B2 (enExample) |
| CN (1) | CN101360422B (enExample) |
| AU (1) | AU2006318212C1 (enExample) |
| CA (1) | CA2631082C (enExample) |
| RU (1) | RU2448703C2 (enExample) |
| WO (1) | WO2007062399A2 (enExample) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
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| PL212489B1 (pl) * | 2008-01-22 | 2012-10-31 | Univ Jagiellonski | Pochodne fenoksyalkiloaminoalkanoli i ich zastosowania |
| CN101983188A (zh) * | 2008-04-01 | 2011-03-02 | 安斯泰来制药有限公司 | 吲哚啉酮化合物 |
| WO2010001325A2 (en) * | 2008-06-30 | 2010-01-07 | Silenseed Ltd | Methods, compositions and systems for local delivery of drugs |
| US8304421B2 (en) | 2008-09-30 | 2012-11-06 | Vanderbilt University | Indole compounds and their use as radiation sensitizing agents and chemotherapeutic agents |
| US9962368B2 (en) | 2009-01-09 | 2018-05-08 | Board Of Regents Of The University Of Texas System | Pro-neurogenic compounds |
| US8362277B2 (en) | 2009-01-09 | 2013-01-29 | Board Of Regents Of The University Of Texas System | Pro-neurogenic compounds |
| US9162980B2 (en) | 2009-01-09 | 2015-10-20 | Board Of Regents Of The University Of Texas System | Anti-depression compounds |
| CN102405043B (zh) | 2009-01-09 | 2017-08-22 | 得克萨斯州大学系统董事会 | 前神经原性化合物 |
| WO2011060976A1 (en) * | 2009-11-20 | 2011-05-26 | Universite De Liege | Tryptamine-derived compounds as antibacterial agents |
| EP2513174B1 (en) * | 2009-12-16 | 2014-06-25 | University Of New Hampshire | Emulsion polymerization of esters of itaconic acid |
| CA2804161A1 (en) | 2010-07-07 | 2012-01-12 | Board Of Regents Of The University Of Texas System | Pro-neurogenic compounds |
| WO2012138739A2 (en) | 2011-04-06 | 2012-10-11 | Chemo-Enhanced Llc | Compositions and methods for treating cancer |
| US9474730B2 (en) * | 2012-04-30 | 2016-10-25 | Board Of Regents Of The University Of Texas System | Methods and compositions for use with K-ras mediated disorders |
| US9701676B2 (en) | 2012-08-24 | 2017-07-11 | Board Of Regents Of The University Of Texas System | Pro-neurogenic compounds |
| CA2895237C (en) | 2013-01-10 | 2021-10-05 | Merck Patent Gmbh | Piperidinylcarbazole as antimalarial |
| WO2014110555A1 (en) * | 2013-01-14 | 2014-07-17 | Chemo-Enchanced Llc | Compositions and methods for treating cancer |
| WO2014145576A2 (en) | 2013-03-15 | 2014-09-18 | Northwestern University | Substituted pyrrolo(2,3-d)pyrimidines for the treatment of cancer |
| EP3068388A4 (en) | 2013-11-11 | 2017-04-12 | Board of Regents of the University of Texas System | Neuroprotective compounds and use thereof |
| WO2015070237A1 (en) | 2013-11-11 | 2015-05-14 | Board Of Regents Of The University Of Texas System | Neuroprotective chemicals and methods for identifying and using same |
| CA2950581A1 (en) * | 2014-05-30 | 2015-12-03 | The Trustees Of Columbia University In The City Of New York | Multivalent ras binding compounds |
| WO2015192343A1 (en) * | 2014-06-18 | 2015-12-23 | Guangzhou Institutes Of Biomedicine And Health, Chinese Academy Of Sciences | P53 activator small molecules |
| CN106573918B (zh) | 2014-07-04 | 2020-06-16 | 默克专利股份有限公司 | 具有抗寄生虫活性的氮杂环庚烷基衍生物和包含它们的药物组合物 |
| AU2016381509A1 (en) * | 2015-12-31 | 2018-07-19 | Syracuse University | Tryptamine-based SHIP inhibitors for the treatment of cancer |
| CA3010615C (en) | 2016-01-14 | 2024-02-20 | Beth Israel Deaconess Medical Center, Inc. | Mast-cell modulators and uses thereof |
| US10918650B2 (en) * | 2016-06-02 | 2021-02-16 | University Of South Florida | Method of treating melanoma using an inhibitor of an atypical protein kinase C |
| EP3515449B1 (en) | 2016-09-26 | 2023-07-12 | Dana-Farber Cancer Institute, Inc. | Quinoline derivatives as chromobox (cbx) protein inhibitors for treating cancer |
| JOP20190086A1 (ar) | 2016-10-21 | 2019-04-18 | Novartis Ag | مشتقات نافثيريدينون جديدة واستخدامها في معالجة عدم انتظام ضربات القلب |
| CN110291084A (zh) | 2016-12-15 | 2019-09-27 | 加利福尼亚大学董事会 | 用于治疗癌症的组合物和方法 |
| CN108251377B (zh) * | 2018-01-16 | 2021-08-27 | 内蒙古大学 | 利用携带Xist Tale抑制性转录因子R6的R6-MEF制备饲养层细胞的方法 |
| US10738139B2 (en) | 2018-12-18 | 2020-08-11 | Itaconix Corporation | Decarboxylation and amidation of polyitaconic acid polymers |
| KR102620902B1 (ko) * | 2020-04-24 | 2024-01-04 | 가천대학교 산학협력단 | 신규 알파-시누클레인 방사성 리간드 및 이를 포함하는 신경퇴행성 질환 진단용 조성물 |
| KR102428024B1 (ko) * | 2020-06-11 | 2022-08-03 | 충북대학교 산학협력단 | 프로카스파제-3의 활성화제로서 신규한 (e)-n-아릴리덴-1-(4-클로로벤질)-1h-인돌-3-카보하이드라지드 및 이를 유효성분으로 포함하는 항암제 조성물 |
| KR102617885B1 (ko) * | 2021-05-07 | 2023-12-27 | 충북대학교 산학협력단 | 신규한 (e)-n'-((1-(4-클로로벤질)-1h-인돌-3-일)메틸렌)-2-(4-옥소퀴나졸린-3(4h)-일)아세토히드라지드 화합물 및 이를 유효성분으로 포함하는 항암제 조성물 |
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| US6436965B1 (en) | 2000-03-02 | 2002-08-20 | Merck Frosst Canada & Co. | PDE IV inhibiting amides, compositions and methods of treatment |
| AU2001251445A1 (en) * | 2000-04-10 | 2001-10-23 | Merck And Co., Inc. | Inhibitors of prenyl-protein transferase |
| US6787651B2 (en) | 2000-10-10 | 2004-09-07 | Smithkline Beecham Corporation | Substituted indoles, pharmaceutical compounds containing such indoles and their use as PPAR-γ binding agents |
| WO2003022274A2 (en) * | 2001-09-13 | 2003-03-20 | Synta Pharmaceuticals Corp. | 2-aroylimidazole compounds for treating cancer |
| NZ543853A (en) * | 2003-06-05 | 2009-09-25 | Zentaris Gmbh | Indole derivatives with apoptosis-inducing effect |
| EP1484329A1 (de) * | 2003-06-06 | 2004-12-08 | Zentaris GmbH | Indolderivate mit Apoptose induzierender Wirkung |
| US7371875B2 (en) * | 2004-03-12 | 2008-05-13 | Miikana Therapeutics, Inc. | Cytotoxic agents and methods of use |
-
2006
- 2006-11-22 AU AU2006318212A patent/AU2006318212C1/en not_active Ceased
- 2006-11-22 US US12/094,739 patent/US8883841B2/en active Active
- 2006-11-22 JP JP2008542528A patent/JP5460054B2/ja not_active Expired - Fee Related
- 2006-11-22 EP EP06840010.0A patent/EP1956910B1/en not_active Not-in-force
- 2006-11-22 WO PCT/US2006/061219 patent/WO2007062399A2/en not_active Ceased
- 2006-11-22 RU RU2008125065/15A patent/RU2448703C2/ru not_active IP Right Cessation
- 2006-11-22 CA CA2631082A patent/CA2631082C/en not_active Expired - Fee Related
- 2006-11-22 CN CN2006800516184A patent/CN101360422B/zh not_active Expired - Fee Related
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