JP2006502214A5 - - Google Patents
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- Publication number
- JP2006502214A5 JP2006502214A5 JP2004542927A JP2004542927A JP2006502214A5 JP 2006502214 A5 JP2006502214 A5 JP 2006502214A5 JP 2004542927 A JP2004542927 A JP 2004542927A JP 2004542927 A JP2004542927 A JP 2004542927A JP 2006502214 A5 JP2006502214 A5 JP 2006502214A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- dinitroanilino
- bromoethyl
- carbonyl
- ethyl methanesulfonate
- 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 2-((2-bromoethyl) 5-{[(2-hydroxyethyl) amino] carbonyl} -2,4-dinitroanilino) ethyl Chemical group 0.000 claims 26
- 150000001875 compounds Chemical class 0.000 claims 16
- 238000000034 method Methods 0.000 claims 12
- 235000003351 Brassica cretica Nutrition 0.000 claims 8
- 235000003343 Brassica rupestris Nutrition 0.000 claims 8
- 235000010460 mustard Nutrition 0.000 claims 8
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical class [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 claims 8
- 102000004459 Nitroreductase Human genes 0.000 claims 7
- 108020001162 nitroreductase Proteins 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000003277 amino group Chemical group 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 150000003512 tertiary amines Chemical class 0.000 claims 6
- 210000004027 cell Anatomy 0.000 claims 5
- 239000000651 prodrug Substances 0.000 claims 5
- 229940002612 prodrug Drugs 0.000 claims 5
- 238000002560 therapeutic procedure Methods 0.000 claims 5
- 241000219198 Brassica Species 0.000 claims 4
- 241000219193 Brassicaceae Species 0.000 claims 4
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 claims 4
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 claims 4
- 239000002798 polar solvent Substances 0.000 claims 4
- 108090000623 proteins and genes Proteins 0.000 claims 4
- 239000000126 substance Substances 0.000 claims 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- 241001112696 Clostridia Species 0.000 claims 3
- 241000588724 Escherichia coli Species 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 229910001508 alkali metal halide Inorganic materials 0.000 claims 3
- 150000008045 alkali metal halides Chemical class 0.000 claims 3
- 230000001419 dependent effect Effects 0.000 claims 3
- 229940017219 methyl propionate Drugs 0.000 claims 3
- 101150091037 nfsB gene Proteins 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 230000002194 synthesizing effect Effects 0.000 claims 3
- 210000004881 tumor cell Anatomy 0.000 claims 3
- AZICEEZSDKZDHX-UHFFFAOYSA-N 2-[n-(2-bromoethyl)-2-(2-hydroxyethylcarbamoyl)-4,6-dinitroanilino]ethyl methanesulfonate Chemical compound CS(=O)(=O)OCCN(CCBr)C1=C(C(=O)NCCO)C=C([N+]([O-])=O)C=C1[N+]([O-])=O AZICEEZSDKZDHX-UHFFFAOYSA-N 0.000 claims 2
- KQNJLOZYSLLLQE-UHFFFAOYSA-N 2-[n-(2-bromoethyl)-2-(2-hydroxypropylcarbamoyl)-4,6-dinitroanilino]ethyl methanesulfonate Chemical compound CC(O)CNC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1N(CCBr)CCOS(C)(=O)=O KQNJLOZYSLLLQE-UHFFFAOYSA-N 0.000 claims 2
- BDBWGNXWWSWBBX-UHFFFAOYSA-N 2-[n-(2-bromoethyl)-2-carbamoyl-4,6-dinitroanilino]ethyl methanesulfonate Chemical compound CS(=O)(=O)OCCN(CCBr)C1=C(C(N)=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O BDBWGNXWWSWBBX-UHFFFAOYSA-N 0.000 claims 2
- LHJUHUSJGFZIGY-UHFFFAOYSA-N 2-[n-(2-bromoethyl)-5-carbamoyl-2,4-dinitroanilino]ethyl methanesulfonate Chemical compound CS(=O)(=O)OCCN(CCBr)C1=CC(C(N)=O)=C([N+]([O-])=O)C=C1[N+]([O-])=O LHJUHUSJGFZIGY-UHFFFAOYSA-N 0.000 claims 2
- 125000005999 2-bromoethyl group Chemical group 0.000 claims 2
- 108090000790 Enzymes Proteins 0.000 claims 2
- 102000004190 Enzymes Human genes 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- 150000001204 N-oxides Chemical class 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 238000010317 ablation therapy Methods 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 claims 2
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims 2
- TVGZVOAGMXONFJ-UHFFFAOYSA-N 2-[2-(2-hydroxyethylcarbamoyl)-n-(2-iodoethyl)-4,6-dinitroanilino]ethyl methanesulfonate Chemical compound CS(=O)(=O)OCCN(CCI)C1=C(C(=O)NCCO)C=C([N+]([O-])=O)C=C1[N+]([O-])=O TVGZVOAGMXONFJ-UHFFFAOYSA-N 0.000 claims 1
- BLCMUMHBRDDXAM-UHFFFAOYSA-N 2-[2-carbamoyl-n-(2-chloroethyl)-4,6-dinitroanilino]ethyl methanesulfonate Chemical compound CS(=O)(=O)OCCN(CCCl)C1=C(C(N)=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O BLCMUMHBRDDXAM-UHFFFAOYSA-N 0.000 claims 1
- RPEHTIARZISZKN-UHFFFAOYSA-N 2-[5-carbamoyl-n-(2-iodoethyl)-2,4-dinitroanilino]ethyl methanesulfonate Chemical compound CS(=O)(=O)OCCN(CCI)C1=CC(C(N)=O)=C([N+]([O-])=O)C=C1[N+]([O-])=O RPEHTIARZISZKN-UHFFFAOYSA-N 0.000 claims 1
- YIBANNNXXGVGBK-UHFFFAOYSA-N 5-[2-bromoethyl(2-chloroethyl)amino]-2,4-dinitrobenzamide Chemical compound NC(=O)C1=CC(N(CCCl)CCBr)=C([N+]([O-])=O)C=C1[N+]([O-])=O YIBANNNXXGVGBK-UHFFFAOYSA-N 0.000 claims 1
- 101710112752 Cytotoxin Proteins 0.000 claims 1
- 206010021143 Hypoxia Diseases 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 239000012491 analyte Substances 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- MGWVXCJVOQWUQG-UHFFFAOYSA-N bromomethanesulfonic acid Chemical compound OS(=O)(=O)CBr MGWVXCJVOQWUQG-UHFFFAOYSA-N 0.000 claims 1
- 230000000981 bystander Effects 0.000 claims 1
- 231100000599 cytotoxic agent Toxicity 0.000 claims 1
- 239000002619 cytotoxin Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 230000007954 hypoxia Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 claims 1
- 230000008685 targeting Effects 0.000 claims 1
- 0 BCCN(CC*)c(cc1*)c(*)cc1[N+]([O-])=O Chemical compound BCCN(CC*)c(cc1*)c(*)cc1[N+]([O-])=O 0.000 description 3
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NZ521851A NZ521851A (en) | 2002-10-08 | 2002-10-08 | Nitroaniline-based unsymmetrical mustard alkylating agents for gene dependent enzyme prodrug therapy |
| NZ521851 | 2002-10-08 | ||
| PCT/NZ2003/000225 WO2004033415A1 (en) | 2002-10-08 | 2003-10-08 | Nitroaniline-based alkylating agents and their use as prodrugs |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010136139A Division JP2010265272A (ja) | 2002-10-08 | 2010-06-15 | ニトロアニリン系のアルキル化剤およびそれらのプロドラッグとしての使用 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| JP2006502214A JP2006502214A (ja) | 2006-01-19 |
| JP2006502214A6 JP2006502214A6 (ja) | 2006-04-06 |
| JP2006502214A5 true JP2006502214A5 (https=) | 2006-11-16 |
| JP4582519B2 JP4582519B2 (ja) | 2010-11-17 |
Family
ID=32089872
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004542927A Expired - Fee Related JP4582519B2 (ja) | 2002-10-08 | 2003-10-08 | ニトロアニリン系のアルキル化剤およびそれらのプロドラッグとしての使用 |
| JP2010136139A Withdrawn JP2010265272A (ja) | 2002-10-08 | 2010-06-15 | ニトロアニリン系のアルキル化剤およびそれらのプロドラッグとしての使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010136139A Withdrawn JP2010265272A (ja) | 2002-10-08 | 2010-06-15 | ニトロアニリン系のアルキル化剤およびそれらのプロドラッグとしての使用 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7776924B2 (https=) |
| EP (1) | EP1558568A4 (https=) |
| JP (2) | JP4582519B2 (https=) |
| CN (1) | CN100546976C (https=) |
| AU (1) | AU2003278628B2 (https=) |
| CA (1) | CA2501388C (https=) |
| NZ (1) | NZ521851A (https=) |
| WO (1) | WO2004033415A1 (https=) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2004285831B2 (en) * | 2003-10-31 | 2011-09-15 | Auckland Uniservices Limited | Novel nitrophenyl mustard and nitrophenylaziridine alcohols and their corresponding phosphates and their use as targeted cytotoxic agents |
| JP4761899B2 (ja) * | 2005-09-12 | 2011-08-31 | Ｈｏｙａ株式会社 | 電子内視鏡システム |
| NZ549659A (en) * | 2006-09-04 | 2008-12-24 | Auckland Uniservices Ltd | Processes of preparing asymmetric dinitrobenzamide mustard compounds, intermediate compounds useful therein and products obtained therefrom |
| EP2350664B1 (en) | 2008-10-21 | 2021-05-19 | ImmunoGenesis, Inc. | Treatment of cancer using the hypoxia activated prodrug th-302 in combination with docetaxel or pemetrexed |
| CN101723932B (zh) * | 2008-10-31 | 2013-11-20 | 北京以岭生物工程技术有限公司 | 硝基吡啶乙烯亚胺化合物、其药物组合物及其制备方法和用途 |
| ES2877629T3 (es) | 2010-07-12 | 2021-11-17 | Immunogenesis Inc | Administración de profármacos activados por hipoxia y agentes antiangiogénicos para el tratamiento del cáncer |
| EP2793882A4 (en) | 2011-12-22 | 2015-04-29 | Threshold Pharmaceuticals Inc | ADMINISTRATION OF HYPOXIA-ACTIVATED PRODRUGS IN COMBINATION WITH CHK1 INHIBITORS FOR THE TREATMENT OF CANCER |
| EP2888227B1 (en) * | 2012-08-23 | 2020-07-29 | Convert Pharmaceuticals SA | Novel prodrugs and methods of use thereof |
| US10202408B2 (en) | 2012-08-23 | 2019-02-12 | Health Innovation Ventures B.V. | Prodrugs and methods of use thereof |
| WO2014062856A1 (en) | 2012-10-16 | 2014-04-24 | Halozyme, Inc. | Hypoxia and hyaluronan and markers thereof for diagnosis and monitoring of diseases and conditions and related methods |
| JP2016528217A (ja) | 2013-07-26 | 2016-09-15 | スレッショルド ファーマシューティカルズ，インコーポレイテッド | 低酸素活性化プロドラッグおよびタキサンの組合せを用いた膵臓癌の治療 |
| BR112017007765B1 (pt) | 2014-10-14 | 2023-10-03 | Halozyme, Inc | Composições de adenosina deaminase-2 (ada2), variantes do mesmo e métodos de usar o mesmo |
| JP7327900B2 (ja) | 2015-06-24 | 2023-08-16 | スレッシュホールド ファーマシューティカルズ， インコーポレイテッド | アジリジン含有ｄｎａアルキル化剤 |
| CN106995815B (zh) * | 2016-01-22 | 2020-09-01 | 南京农业大学 | 硝基还原酶基因pnr及其编码的蛋白和应用 |
| CN106905184B (zh) * | 2017-03-05 | 2019-03-29 | 北京化工大学 | 含有苯甲酰胺基团的氮芥类化合物及其制备方法和用途 |
| EP3774743B1 (en) * | 2018-03-29 | 2023-11-22 | Achilles Medical Limited | Prodrug compounds activated by akr1c3 and their use for treating hyperproliferative disorders |
| CN112961082B (zh) * | 2021-02-22 | 2022-09-06 | 沈阳药科大学 | 一种血管阻断剂与双载药仿生脂质体联用的给药系统 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8705477D0 (en) | 1987-03-09 | 1987-04-15 | Carlton Med Prod | Drug delivery systems |
| NZ240785A (en) * | 1991-11-28 | 1995-08-28 | Cancer Res Campaign Tech | Substituted nitro aniline derivatives and medicaments |
-
2002
- 2002-10-08 NZ NZ521851A patent/NZ521851A/en not_active IP Right Cessation
-
2003
- 2003-10-08 US US10/529,772 patent/US7776924B2/en not_active Expired - Fee Related
- 2003-10-08 AU AU2003278628A patent/AU2003278628B2/en not_active Ceased
- 2003-10-08 CA CA2501388A patent/CA2501388C/en not_active Expired - Fee Related
- 2003-10-08 WO PCT/NZ2003/000225 patent/WO2004033415A1/en not_active Ceased
- 2003-10-08 JP JP2004542927A patent/JP4582519B2/ja not_active Expired - Fee Related
- 2003-10-08 EP EP03770163A patent/EP1558568A4/en not_active Withdrawn
- 2003-10-08 CN CNB2003801028127A patent/CN100546976C/zh not_active Expired - Fee Related
-
2010
- 2010-06-15 JP JP2010136139A patent/JP2010265272A/ja not_active Withdrawn
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