JP2010508292A5 - - Google Patents
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- JP2010508292A5 JP2010508292A5 JP2009534863A JP2009534863A JP2010508292A5 JP 2010508292 A5 JP2010508292 A5 JP 2010508292A5 JP 2009534863 A JP2009534863 A JP 2009534863A JP 2009534863 A JP2009534863 A JP 2009534863A JP 2010508292 A5 JP2010508292 A5 JP 2010508292A5
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- Prior art keywords
- compound
- agent
- compound according
- halogen
- therapeutic agent
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- 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.)
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- 150000001875 compounds Chemical class 0.000 claims description 80
- 239000002254 cytotoxic agent Substances 0.000 claims description 17
- 229940127089 cytotoxic agent Drugs 0.000 claims description 17
- 231100000599 cytotoxic agent Toxicity 0.000 claims description 17
- 239000003814 drug Substances 0.000 claims description 17
- 229940124597 therapeutic agent Drugs 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 11
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 9
- 206010021143 Hypoxia Diseases 0.000 claims description 9
- 229910052796 boron Inorganic materials 0.000 claims description 9
- 229910052755 nonmetal Inorganic materials 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 229920000570 polyether Polymers 0.000 claims description 6
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 5
- 238000001514 detection method Methods 0.000 claims description 5
- 230000001146 hypoxic effect Effects 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 claims description 4
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims description 4
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 230000007954 hypoxia Effects 0.000 claims description 4
- 229960003330 pentetic acid Drugs 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 239000002534 radiation-sensitizing agent Substances 0.000 claims description 4
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 3
- 229930012538 Paclitaxel Natural products 0.000 claims description 3
- 208000005017 glioblastoma Diseases 0.000 claims description 3
- 208000002409 gliosarcoma Diseases 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Chemical group 0.000 claims description 3
- 238000002595 magnetic resonance imaging Methods 0.000 claims description 3
- 201000001441 melanoma Diseases 0.000 claims description 3
- 229960001592 paclitaxel Drugs 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- -1 tubulin inhibitor Substances 0.000 claims description 3
- PAEZRCINULFAGO-OAQYLSRUSA-N (R)-homocamptothecin Chemical compound CC[C@@]1(O)CC(=O)OCC(C2=O)=C1C=C1N2CC2=CC3=CC=CC=C3N=C21 PAEZRCINULFAGO-OAQYLSRUSA-N 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- LGZKGOGODCLQHG-CYBMUJFWSA-N 5-[(2r)-2-hydroxy-2-(3,4,5-trimethoxyphenyl)ethyl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC=C1C[C@@H](O)C1=CC(OC)=C(OC)C(OC)=C1 LGZKGOGODCLQHG-CYBMUJFWSA-N 0.000 claims description 2
- 229960005532 CC-1065 Drugs 0.000 claims description 2
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 claims description 2
- 229940123780 DNA topoisomerase I inhibitor Drugs 0.000 claims description 2
- 229940124087 DNA topoisomerase II inhibitor Drugs 0.000 claims description 2
- 206010061218 Inflammation Diseases 0.000 claims description 2
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 2
- WDLRUFUQRNWCPK-UHFFFAOYSA-N Tetraxetan Chemical compound OC(=O)CN1CCN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CC1 WDLRUFUQRNWCPK-UHFFFAOYSA-N 0.000 claims description 2
- 239000000365 Topoisomerase I Inhibitor Substances 0.000 claims description 2
- 239000000317 Topoisomerase II Inhibitor Substances 0.000 claims description 2
- 229940122429 Tubulin inhibitor Drugs 0.000 claims description 2
- 239000000556 agonist Substances 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 239000005557 antagonist Substances 0.000 claims description 2
- 239000003242 anti bacterial agent Substances 0.000 claims description 2
- 230000001028 anti-proliverative effect Effects 0.000 claims description 2
- 239000002256 antimetabolite Substances 0.000 claims description 2
- 229940034982 antineoplastic agent Drugs 0.000 claims description 2
- 239000002246 antineoplastic agent Substances 0.000 claims description 2
- 230000006907 apoptotic process Effects 0.000 claims description 2
- 230000003115 biocidal effect Effects 0.000 claims description 2
- 229940127093 camptothecin Drugs 0.000 claims description 2
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical group C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 claims description 2
- 239000002738 chelating agent Substances 0.000 claims description 2
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 2
- 229960004316 cisplatin Drugs 0.000 claims description 2
- 229960001338 colchicine Drugs 0.000 claims description 2
- LGZKGOGODCLQHG-UHFFFAOYSA-N combretastatin Natural products C1=C(O)C(OC)=CC=C1CC(O)C1=CC(OC)=C(OC)C(OC)=C1 LGZKGOGODCLQHG-UHFFFAOYSA-N 0.000 claims description 2
- VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 claims description 2
- 229960004679 doxorubicin Drugs 0.000 claims description 2
- YJGVMLPVUAXIQN-UHFFFAOYSA-N epipodophyllotoxin Natural products COC1=C(OC)C(OC)=CC(C2C3=CC=4OCOC=4C=C3C(O)C3C2C(OC3)=O)=C1 YJGVMLPVUAXIQN-UHFFFAOYSA-N 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 2
- 239000005556 hormone Substances 0.000 claims description 2
- 229940088597 hormone Drugs 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 239000002955 immunomodulating agent Substances 0.000 claims description 2
- 229940121354 immunomodulator Drugs 0.000 claims description 2
- 230000002584 immunomodulator Effects 0.000 claims description 2
- 230000004054 inflammatory process Effects 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- 208000028867 ischemia Diseases 0.000 claims description 2
- 229960000485 methotrexate Drugs 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 229960001237 podophyllotoxin Drugs 0.000 claims description 2
- YJGVMLPVUAXIQN-XVVDYKMHSA-N podophyllotoxin Chemical compound COC1=C(OC)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@H](O)[C@@H]3[C@@H]2C(OC3)=O)=C1 YJGVMLPVUAXIQN-XVVDYKMHSA-N 0.000 claims description 2
- YVCVYCSAAZQOJI-UHFFFAOYSA-N podophyllotoxin Natural products COC1=C(O)C(OC)=CC(C2C3=CC=4OCOC=4C=C3C(O)C3C2C(OC3)=O)=C1 YVCVYCSAAZQOJI-UHFFFAOYSA-N 0.000 claims description 2
- 238000002600 positron emission tomography Methods 0.000 claims description 2
- 230000003389 potentiating effect Effects 0.000 claims description 2
- 238000004611 spectroscopical analysis Methods 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical group [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical group [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims 2
- 239000010931 gold Substances 0.000 claims 2
- 229910052737 gold Inorganic materials 0.000 claims 2
- 239000002245 particle Substances 0.000 claims 2
- 102000004190 Enzymes Human genes 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- AMRJKAQTDDKMCE-UHFFFAOYSA-N dolastatin Chemical compound CC(C)C(N(C)C)C(=O)NC(C(C)C)C(=O)N(C)C(C(C)C)C(OC)CC(=O)N1CCCC1C(OC)C(C)C(=O)NC(C=1SC=CN=1)CC1=CC=CC=C1 AMRJKAQTDDKMCE-UHFFFAOYSA-N 0.000 claims 1
- 229930188854 dolastatin Natural products 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 150000002843 nonmetals Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 description 20
- 210000004027 cell Anatomy 0.000 description 8
- 201000011510 cancer Diseases 0.000 description 4
- 230000003211 malignant effect Effects 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/588,634 | 2006-10-27 | ||
| US11/588,634 US7842278B2 (en) | 2006-10-27 | 2006-10-27 | Hypoxia-selective, weakly basic 2-nitroimidazole delivery agents and methods of use thereof |
| PCT/US2007/082548 WO2008070336A2 (en) | 2006-10-27 | 2007-10-25 | Hypoxia-selective, weakly basic 2-nitroimidazole delivery agents and methods of use thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010508292A JP2010508292A (ja) | 2010-03-18 |
| JP2010508292A5 true JP2010508292A5 (https=) | 2011-01-20 |
| JP5421114B2 JP5421114B2 (ja) | 2014-02-19 |
Family
ID=39330426
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009534863A Expired - Fee Related JP5421114B2 (ja) | 2006-10-27 | 2007-10-25 | 低酸素症選択性の弱塩基性２−ニトロイミダゾール送達薬剤およびその使用方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US7842278B2 (https=) |
| EP (1) | EP2101825A4 (https=) |
| JP (1) | JP5421114B2 (https=) |
| CN (1) | CN101668547B (https=) |
| CA (1) | CA2667684C (https=) |
| WO (1) | WO2008070336A2 (https=) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9056136B2 (en) * | 2006-10-06 | 2015-06-16 | Natural Pharmacia International, Inc. | Weakly basic 2-nitroimidazoles for the non-invasive detection of tissue hypoxia |
| US7842278B2 (en) * | 2006-10-27 | 2010-11-30 | Natural Pharmacia International, Inc. | Hypoxia-selective, weakly basic 2-nitroimidazole delivery agents and methods of use thereof |
| US8344337B2 (en) * | 2010-04-21 | 2013-01-01 | Axcelis Technologies, Inc. | Silaborane implantation processes |
| JP5816896B2 (ja) * | 2011-01-26 | 2015-11-18 | ステラファーマ株式会社 | カルボラン修飾コウジ酸／シクロデキストリン包接錯体およびその製造方法 |
| US8741250B2 (en) | 2011-08-05 | 2014-06-03 | The Curators Of The University Of Missouri | Hydroxylation of icosahedral boron compounds |
| US9217002B2 (en) | 2011-09-15 | 2015-12-22 | The Curators Of The University Of Missouri | Cluster boron compounds and uses thereof |
| MD4150C1 (ro) * | 2011-10-11 | 2012-09-30 | Институт Химии Академии Наук Молдовы | Procedeu de obţinere a compuşilor coordinativi ai Co(II), Ni(II) şi Zn(II) cu 2-nitro-4,5-difenilimidazol pornind de la 4,5-difenilimidazol şi nitraţii metalelor respective |
| US9382267B2 (en) | 2011-11-30 | 2016-07-05 | The Curators Of The University Of Missouri | Small molecule inhibitors of nicotinamide phosphoribosyltransferase (NAMPT) |
| WO2013082150A1 (en) * | 2011-11-30 | 2013-06-06 | The Curators Of The University Of Missouri | Small molecule inhibitors of nicotinamide phosphoribosyltransferase (nampt) |
| US9655975B2 (en) * | 2012-02-13 | 2017-05-23 | University Of Tsukuba | Prodrug using nitroimidazole |
| MD4178C1 (ro) * | 2012-02-27 | 2013-02-28 | Институт Химии Академии Наук Молдовы | Procedeu de obţinere a 2-nitro-4,5-difenilimidazolului |
| EP2983674A4 (en) | 2013-04-08 | 2017-05-10 | Dennis M. Brown | Therapeutic benefit of suboptimally administered chemical compounds |
| CN105764501A (zh) | 2013-07-26 | 2016-07-13 | 现代化制药公司 | 改善比生群治疗效益的组合物 |
| US10076578B2 (en) * | 2014-10-01 | 2018-09-18 | Vanderbilt University | Probes for imaging of hypoxia |
| US20180185522A1 (en) * | 2014-12-12 | 2018-07-05 | Oxford University Innovation Limited | Contrast agent for imaging hypoxia |
| US10695446B2 (en) * | 2015-05-01 | 2020-06-30 | Vanderbilt University | Composition and method for detecting hypoxia |
| CN106928265B (zh) * | 2015-09-23 | 2019-01-15 | 苏州大学 | 一种碳硼烷基高氯酸铵的制备方法 |
| WO2017181790A1 (zh) * | 2016-04-19 | 2017-10-26 | 南京中硼联康医疗科技有限公司 | 用于消除β淀粉样蛋白沉积斑块的中子捕获治疗系统 |
| CN106977501A (zh) * | 2017-03-20 | 2017-07-25 | 华东师范大学 | 一种基于2‑硝基咪唑‑1‑烷基醇的低氧激活前药 |
| CN109959612A (zh) * | 2017-12-14 | 2019-07-02 | 深圳先进技术研究院 | 一种光声探针在制备ntr光声检测试剂中的应用 |
| CN109956932A (zh) * | 2017-12-14 | 2019-07-02 | 深圳先进技术研究院 | 一种可激活型光敏剂在制备肿瘤光热治疗试剂中的应用 |
| US20240424011A1 (en) * | 2021-12-21 | 2024-12-26 | University Of Tsukuba | Combination therapy of hypoxia-responsive prodrug of an anticancer drug and radiotherapy, and novel hypoxia-responsive prodrug |
| CN115581780A (zh) * | 2022-11-03 | 2023-01-10 | 北京大学深圳研究生院 | 诊疗一体化核素药物、应用、药物制剂及其制备方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE47132B1 (en) * | 1977-08-19 | 1983-12-28 | Roche Products Ltd | Novel nitroimidazoles and pharmaceutical preparations containing these as well as their manufacture |
| US4282232A (en) | 1979-04-26 | 1981-08-04 | Research Corporation | Nitroimidazole radiosensitizers for hypoxic tumor cells and compositions thereof |
| US4631289A (en) * | 1982-05-27 | 1986-12-23 | National Research Development Corporation | Useful in radiotherapy of chemotherapy 4-aziridino-1-nitroimidazol-1-yl-2,3-butanediols |
| US4797397A (en) | 1987-07-31 | 1989-01-10 | Warner-Lambert Company | 2-nitroimidazole derivatives useful as radiosensitizers for hypoxic tumor cells |
| CA1332738C (en) * | 1987-12-04 | 1994-10-25 | Gerald Edward Adams | Nitro-substituted aromatic or hetero-aromatic compounds for use in cancer treatment |
| US5086068A (en) * | 1988-02-26 | 1992-02-04 | Alberta Cancer Board | Immunochemical detection of hypoxia in normal and tumor tissue |
| GB9113487D0 (en) * | 1991-06-21 | 1991-08-07 | Amersham Int Plc | Agents for hypoxic cells |
| GB9219565D0 (en) * | 1992-09-16 | 1992-10-28 | Adams Gerald E | Novel bioreductive compounds |
| US5674693A (en) * | 1994-03-18 | 1997-10-07 | Natural Pharmacia International Inc. | Derivatives of 2-nitro-imidazoles as hypoxic cell markers |
| WO2000043004A1 (en) * | 1999-01-26 | 2000-07-27 | Fox Chase Cancer Center | 1,4,8,11-tetraazacyclotetradecane derivatives as radiodiganostic agents and their use in determining hypoxia and radioresistance of tumors |
| US9056136B2 (en) | 2006-10-06 | 2015-06-16 | Natural Pharmacia International, Inc. | Weakly basic 2-nitroimidazoles for the non-invasive detection of tissue hypoxia |
| US7842278B2 (en) * | 2006-10-27 | 2010-11-30 | Natural Pharmacia International, Inc. | Hypoxia-selective, weakly basic 2-nitroimidazole delivery agents and methods of use thereof |
-
2006
- 2006-10-27 US US11/588,634 patent/US7842278B2/en not_active Expired - Fee Related
-
2007
- 2007-10-25 JP JP2009534863A patent/JP5421114B2/ja not_active Expired - Fee Related
- 2007-10-25 EP EP07871243A patent/EP2101825A4/en not_active Withdrawn
- 2007-10-25 WO PCT/US2007/082548 patent/WO2008070336A2/en not_active Ceased
- 2007-10-25 CA CA2667684A patent/CA2667684C/en not_active Expired - Fee Related
- 2007-10-25 CN CN200780048105.2A patent/CN101668547B/zh not_active Expired - Fee Related
-
2010
- 2010-11-29 US US12/955,720 patent/US8518371B2/en not_active Expired - Fee Related
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