AU2001273983A1 - Novel prodrugs von 6-hydroxy-2,3-dihydro-1h-indoles, 5-hydroxy-1,2-dihydro-3h-pyrrolo(3,2-e)indoles and 5-hydroxy-1,2-dihydro-3h-benzo(e)indoles as well as of 6-hydroxy-1,2,3,4-tetrahydro-benzo(f)quinoline derivatives for use in selective cancer therapy - Google Patents
Novel prodrugs von 6-hydroxy-2,3-dihydro-1h-indoles, 5-hydroxy-1,2-dihydro-3h-pyrrolo(3,2-e)indoles and 5-hydroxy-1,2-dihydro-3h-benzo(e)indoles as well as of 6-hydroxy-1,2,3,4-tetrahydro-benzo(f)quinoline derivatives for use in selective cancer therapyInfo
- Publication number
- AU2001273983A1 AU2001273983A1 AU2001273983A AU7398301A AU2001273983A1 AU 2001273983 A1 AU2001273983 A1 AU 2001273983A1 AU 2001273983 A AU2001273983 A AU 2001273983A AU 7398301 A AU7398301 A AU 7398301A AU 2001273983 A1 AU2001273983 A1 AU 2001273983A1
- Authority
- AU
- Australia
- Prior art keywords
- hydroxy
- dihydro
- indoles
- benzo
- prodrugs
- 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.)
- Abandoned
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/60—Naphtho [b] pyrroles; Hydrogenated naphtho [b] pyrroles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/02—Heterocyclic radicals containing only nitrogen as ring hetero atoms
Abstract
The chemotherapy of malignant tumours is greatly restricted by the generally slight differentiation of the available cytostatic agents between normal and malignant tissue. In order to achieve an improvement of the selectivity in cancer therapy, novel prodrugs have been developed from 6-hydroxy-2,3-dihydro-1H-indolene, 5-hydroxy-1,2-dihydro-3H-pyrrolo[3,2-e]indolene and 5-hydroxy-1,2-dihydro-3H-benzo[e]indolene as well as from 6-hydroxy-1,2,3,4-tetrahydro-benzo[f]-quinolines, that may be used within the framework of the ADEP therapy (antibody directed enzyme prodrug therapy). The new prodrugs are characterised by a high difference in toxicity between the prodrug and underlying drug and by a very high efficacy of the drug. After splitting off of the glycosidic and/or acetal group on the phenolic hydroxy groups of the prodrugs, a spirocyclopropacyclohexadiene is formed which, being a highly toxic group, effects an alkylation of the DNA or RNA.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2000121335 DE10021335A1 (en) | 2000-05-02 | 2000-05-02 | New 6-hydroxy-2,3-dihydro-1H-indole derivatives, tricyclic analogs and corresponding glycoside prodrugs, are antitumor agents for use in antibody-directed enzymatic prodrug therapy |
DE10021335 | 2000-05-02 | ||
DE10025329A DE10025329A1 (en) | 2000-05-23 | 2000-05-23 | New 6-hydroxy-2,3-dihydro-1H-indole derivatives and analogs, useful in cancer therapy, especially used in low toxicity glycoside or acetal prodrug form for antibody directed enzyme prodrug therapy |
DE10025329 | 2000-05-23 | ||
PCT/EP2001/004904 WO2001083448A2 (en) | 2000-05-02 | 2001-05-02 | Novel prodrugs von 6-hydroxy-2,3-dihydro-1h-indoles, 5-hydroxy-1,2-dihydro-3h-pyrrolo[3,2-e]indoles and 5-hydroxy-1,2-dihydro-3h-benzo(e)indoles as well as of 6-hydroxy-1,2,3,4-tetrahydro-benzo[f]quinoline derivatives for use in selective cancer therapy |
Publications (1)
Publication Number | Publication Date |
---|---|
AU2001273983A1 true AU2001273983A1 (en) | 2001-11-12 |
Family
ID=26005518
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU2001273983A Abandoned AU2001273983A1 (en) | 2000-05-02 | 2001-05-02 | Novel prodrugs von 6-hydroxy-2,3-dihydro-1h-indoles, 5-hydroxy-1,2-dihydro-3h-pyrrolo(3,2-e)indoles and 5-hydroxy-1,2-dihydro-3h-benzo(e)indoles as well as of 6-hydroxy-1,2,3,4-tetrahydro-benzo(f)quinoline derivatives for use in selective cancer therapy |
Country Status (6)
Country | Link |
---|---|
US (1) | US7214685B2 (en) |
EP (1) | EP1280771B1 (en) |
AT (1) | ATE279390T1 (en) |
AU (1) | AU2001273983A1 (en) |
DE (1) | DE50104114D1 (en) |
WO (1) | WO2001083448A2 (en) |
Families Citing this family (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20110313230A1 (en) | 2001-05-11 | 2011-12-22 | Terrance Grant Johns | Specific binding proteins and uses thereof |
US20100056762A1 (en) | 2001-05-11 | 2010-03-04 | Old Lloyd J | Specific binding proteins and uses thereof |
WO2002092771A2 (en) | 2001-05-11 | 2002-11-21 | Ludwig Institute For Cancer Research | Specific binding proteins and uses thereof |
WO2004035571A1 (en) * | 2002-10-15 | 2004-04-29 | Rigel Pharmaceuticals, Inc. | Substituted indoles and their use as hcv inhibitors |
US20050239864A1 (en) * | 2004-04-23 | 2005-10-27 | Yuqiang Wang | Novel tumor-selective chemotherapeutic agents |
RU2489423C2 (en) * | 2006-02-02 | 2013-08-10 | Синтарга Б.В. | Water-soluble analogues cc-1065 and their conjugates |
MX2009007987A (en) | 2007-01-25 | 2010-03-01 | Dana Farber Cancer Inst Inc | Use of anti-egfr antibodies in treatment of egfr mutant mediated disease. |
US9023356B2 (en) | 2007-03-15 | 2015-05-05 | Ludwig Institute For Cancer Research Ltd | Treatment method using EGFR antibodies and SRC inhibitors and related formulations |
US9901567B2 (en) | 2007-08-01 | 2018-02-27 | Syntarga B.V. | Substituted CC-1065 analogs and their conjugates |
EP2173739B1 (en) * | 2007-08-01 | 2013-07-31 | Syntarga B.V. | Substituted cc-1065 analogs and their conjugates |
JP5532486B2 (en) | 2007-08-14 | 2014-06-25 | ルードヴィッヒ インスティテュート フォー キャンサー リサーチ | Monoclonal antibody 175 targeting EGF receptor and derivatives and uses thereof |
US8144909B2 (en) | 2008-08-12 | 2012-03-27 | Cochlear Limited | Customization of bone conduction hearing devices |
MX2011004625A (en) | 2008-11-03 | 2011-07-20 | Syntarga Bv | Novel cc-1065 analogs and their conjugates. |
WO2010096394A2 (en) | 2009-02-17 | 2010-08-26 | Redwood Biosciences, Inc. | Aldehyde-tagged protein-based drug carriers and methods of use |
US20110076232A1 (en) | 2009-09-29 | 2011-03-31 | Ludwig Institute For Cancer Research | Specific binding proteins and uses thereof |
DE102009051438A1 (en) | 2009-10-30 | 2011-05-05 | Georg-August-Universität Göttingen Stiftung Öffentlichen Rechts | fluorescent dyes |
DE102009051799B4 (en) | 2009-11-03 | 2021-07-01 | Georg-August-Universität Göttingen Stiftung Öffentlichen Rechts | Bifunctional Prodrugs and Drugs |
PL2560645T3 (en) | 2010-04-21 | 2017-01-31 | Syntarga B.V. | Conjugates of cc-1065 analogs and bifunctional linkers |
CN101857617A (en) * | 2010-04-28 | 2010-10-13 | 中国海洋大学 | Quinazoline sugar derivative and preparation method and application thereof |
AU2012205301B2 (en) | 2011-01-14 | 2017-01-05 | Redwood Bioscience, Inc. | Aldehyde-tagged immunoglobulin polypeptides and method of use thereof |
CN103503484B (en) | 2011-03-23 | 2017-07-21 | 耳蜗有限公司 | The allotment of hearing device |
SI2820009T1 (en) | 2012-03-01 | 2018-05-31 | Array Biopharma, Inc. | Serine/threonine kinase inhibitors |
MY177390A (en) | 2014-01-10 | 2020-09-14 | Byondis Bv | Method for purifying cys-linked antibody-drug conjugates |
MX368234B (en) | 2014-01-10 | 2019-09-25 | Synthon Biopharmaceuticals Bv | Duocarmycin adcs for use in treatment of endometrial cancer. |
SG10201911860VA (en) | 2014-01-10 | 2020-02-27 | Synthon Biopharmaceuticals Bv | Duocarmycin adcs showing improved in vivo antitumor activity |
ES2785551T3 (en) | 2014-06-30 | 2020-10-07 | Glykos Finland Oy | Saccharide derivative of a toxic payload and its conjugates with antibodies |
AU2017257504A1 (en) | 2016-04-26 | 2018-10-25 | R.P. Scherer Technologies, Llc | Antibody conjugates and methods of making and using the same |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5646298A (en) | 1995-06-07 | 1997-07-08 | Procoron, Inc. | Cyclopropylindole prodrugs |
US5843937A (en) | 1996-05-23 | 1998-12-01 | Panorama Research, Inc. | DNA-binding indole derivatives, their prodrugs and immunoconjugates as anticancer agents |
JP4155598B2 (en) | 1996-09-12 | 2008-09-24 | オークランド ユニサーヴィシズ リミテッド | Condensed N-acylindoles as anticancer agents |
-
2001
- 2001-05-02 EP EP01940388A patent/EP1280771B1/en not_active Expired - Lifetime
- 2001-05-02 DE DE2001504114 patent/DE50104114D1/en not_active Expired - Lifetime
- 2001-05-02 AU AU2001273983A patent/AU2001273983A1/en not_active Abandoned
- 2001-05-02 WO PCT/EP2001/004904 patent/WO2001083448A2/en active IP Right Grant
- 2001-05-02 AT AT01940388T patent/ATE279390T1/en not_active IP Right Cessation
- 2001-05-02 US US10/275,415 patent/US7214685B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
US7214685B2 (en) | 2007-05-08 |
EP1280771A2 (en) | 2003-02-05 |
EP1280771B1 (en) | 2004-10-13 |
WO2001083448A3 (en) | 2002-06-20 |
DE50104114D1 (en) | 2004-11-18 |
US20040033962A1 (en) | 2004-02-19 |
ATE279390T1 (en) | 2004-10-15 |
WO2001083448A2 (en) | 2001-11-08 |
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