JP2005529920A5 - - Google Patents
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- Publication number
- JP2005529920A5 JP2005529920A5 JP2004503474A JP2004503474A JP2005529920A5 JP 2005529920 A5 JP2005529920 A5 JP 2005529920A5 JP 2004503474 A JP2004503474 A JP 2004503474A JP 2004503474 A JP2004503474 A JP 2004503474A JP 2005529920 A5 JP2005529920 A5 JP 2005529920A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- alkyl
- solvent
- camptothecin
- alkyl group
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 claims 16
- 150000001875 compounds Chemical class 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 239000002904 solvent Substances 0.000 claims 7
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 claims 6
- 206010028980 Neoplasm Diseases 0.000 claims 6
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 claims 6
- 229940127093 camptothecin Drugs 0.000 claims 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 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 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 125000003277 amino group Chemical group 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- 150000007524 organic acids Chemical class 0.000 claims 5
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 239000011230 binding agent Substances 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- -1 (CH 2 ) n NR 2 7 Chemical group 0.000 claims 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims 2
- 102000004190 Enzymes Human genes 0.000 claims 2
- 108090000790 Enzymes Proteins 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- 102000003915 DNA Topoisomerases Human genes 0.000 claims 1
- 108090000323 DNA Topoisomerases Proteins 0.000 claims 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical group C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims 1
- 229940068372 acetyl salicylate Drugs 0.000 claims 1
- 229960001138 acetylsalicylic acid Drugs 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 210000000481 breast Anatomy 0.000 claims 1
- 210000003679 cervix uteri Anatomy 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 150000002596 lactones Chemical group 0.000 claims 1
- 210000002429 large intestine Anatomy 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical group CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims 1
- 210000001672 ovary Anatomy 0.000 claims 1
- 210000000496 pancreas Anatomy 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 210000002307 prostate Anatomy 0.000 claims 1
- 210000000664 rectum Anatomy 0.000 claims 1
- 210000002784 stomach Anatomy 0.000 claims 1
- 210000000626 ureter Anatomy 0.000 claims 1
- 210000004291 uterus Anatomy 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/139,778 US6699875B2 (en) | 2002-05-06 | 2002-05-06 | Cascade esters of camptothecins and methods of treating cancer using these compounds |
| PCT/US2003/012399 WO2003095460A1 (en) | 2002-05-06 | 2003-04-22 | Cascade esters of camptothecins and methods of treating cancer using these compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005529920A JP2005529920A (ja) | 2005-10-06 |
| JP2005529920A5 true JP2005529920A5 (https=) | 2006-06-15 |
Family
ID=29418375
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004503474A Withdrawn JP2005529920A (ja) | 2002-05-06 | 2003-04-22 | カンプトテシンのカスケードエステルおよびこれらの化合物を使用する癌治療方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6699875B2 (https=) |
| EP (1) | EP1501837A1 (https=) |
| JP (1) | JP2005529920A (https=) |
| AU (1) | AU2003239157A1 (https=) |
| CA (1) | CA2484815A1 (https=) |
| WO (1) | WO2003095460A1 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040204435A1 (en) * | 2003-04-09 | 2004-10-14 | Joachim Liehr | Alternating treatment with topoisomerase I and topoisomerase II inhibitors |
| WO2007075492A1 (en) * | 2005-12-16 | 2007-07-05 | Sonus Pharmaceuticals, Inc. | Lipophilic anticancer drug compounds |
| TW200731991A (en) * | 2005-12-20 | 2007-09-01 | Sonus Pharma Inc | Lipophilic di(anticancer drug) compounds, compositions and related methods |
| CN101522686A (zh) * | 2006-08-11 | 2009-09-02 | 克里斯特斯斯特林癌症研究基金会 | 制备喜树碱酯的方法 |
| US7572803B2 (en) * | 2007-10-25 | 2009-08-11 | The Christus Stehlin Foundation For Cancer Research | Hydrated crystalline esters of camptothecin |
| US20130121921A1 (en) | 2011-11-11 | 2013-05-16 | The Christus Stehlin Foundation For Cancer Research | Rodent Therapeutic Model And Methods |
| CN103864811A (zh) * | 2012-12-13 | 2014-06-18 | 天津科技大学 | 一种新颖的10-羟基喜树碱20位衍生物制备方法及其在抗肿瘤药物中的应用 |
| CN106588945B (zh) * | 2016-11-16 | 2019-02-12 | 浙江大学 | 阿司匹林抗癌药物偶联物、合成方法及其应用 |
| CN110862403A (zh) * | 2018-08-27 | 2020-03-06 | 遵义医学院 | 喜树碱-羟基乙酸-去甲斑蝥素结合物及其应用 |
| CN115073483B (zh) * | 2022-07-27 | 2022-10-25 | 泽升科技(广州)有限公司 | 一种伊立替康的对映体的制备方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4399282A (en) | 1979-07-10 | 1983-08-16 | Kabushiki Kaisha Yakult Honsha | Camptothecin derivatives |
| US5552154A (en) | 1989-11-06 | 1996-09-03 | The Stehlin Foundation For Cancer Research | Method for treating cancer with water-insoluble s-camptothecin of the closed lactone ring form and derivatives thereof |
| US6080751A (en) | 1992-01-14 | 2000-06-27 | The Stehlin Foundation For Cancer Research | Method for treating pancreatic cancer in humans with water-insoluble S-camptothecin of the closed lactone ring form and derivatives thereof |
| US5880131A (en) | 1993-10-20 | 1999-03-09 | Enzon, Inc. | High molecular weight polymer-based prodrugs |
| US5965566A (en) | 1993-10-20 | 1999-10-12 | Enzon, Inc. | High molecular weight polymer-based prodrugs |
| US5646159A (en) | 1994-07-20 | 1997-07-08 | Research Triangle Institute | Water-soluble esters of camptothecin compounds |
| US5731316A (en) | 1996-01-30 | 1998-03-24 | The Stehlin Foundation For Cancer Research | Derivatives of camptothecin and methods of treating cancer using these derivatives |
| US6407118B1 (en) | 1996-01-30 | 2002-06-18 | The Stehlin Foundation For Cancer Research | Derivatives of camptothecin and methods of treating cancer using these derivatives |
| US6096336A (en) | 1996-01-30 | 2000-08-01 | The Stehlin Foundation For Cancer Research | Liposomal prodrugs comprising derivatives of camptothecin and methods of treating cancer using these prodrugs |
| US5922877A (en) | 1997-08-05 | 1999-07-13 | The Stehlin Foundation For Cancer Research | Methods of preparing and purifying 9-nitro-20-camptothecin |
| US6228855B1 (en) | 1999-08-03 | 2001-05-08 | The Stehlin Foundation For Cancer Research | Aromatic esters of camptothecins and methods to treat cancers |
| US6350756B1 (en) | 2001-01-18 | 2002-02-26 | California Pacific Medical Center | Camptothecin derivatives |
| GB0119578D0 (en) | 2001-08-10 | 2001-10-03 | Pharmacia & Upjohn Spa | Fluoro linkers |
-
2002
- 2002-05-06 US US10/139,778 patent/US6699875B2/en not_active Expired - Lifetime
-
2003
- 2003-04-22 WO PCT/US2003/012399 patent/WO2003095460A1/en not_active Ceased
- 2003-04-22 JP JP2004503474A patent/JP2005529920A/ja not_active Withdrawn
- 2003-04-22 CA CA002484815A patent/CA2484815A1/en not_active Abandoned
- 2003-04-22 AU AU2003239157A patent/AU2003239157A1/en not_active Abandoned
- 2003-04-22 EP EP03733873A patent/EP1501837A1/en not_active Ceased
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