JP2004522779A5 - - Google Patents
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- Publication number
- JP2004522779A5 JP2004522779A5 JP2002567297A JP2002567297A JP2004522779A5 JP 2004522779 A5 JP2004522779 A5 JP 2004522779A5 JP 2002567297 A JP2002567297 A JP 2002567297A JP 2002567297 A JP2002567297 A JP 2002567297A JP 2004522779 A5 JP2004522779 A5 JP 2004522779A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- alkyl
- aralkyl
- nhr
- cooh
- 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
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- 125000000217 alkyl group Chemical group 0.000 description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 13
- 229910052794 bromium Inorganic materials 0.000 description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 12
- 229910052801 chlorine Inorganic materials 0.000 description 12
- 125000001072 heteroaryl group Chemical group 0.000 description 10
- 229910052740 iodine Inorganic materials 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 239000003446 ligand Substances 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 125000006242 amine protecting group Chemical group 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 125000005549 heteroarylene group Chemical group 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- -1 —CONH 2 Chemical group 0.000 description 3
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical group C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
- 0 C*CCN*C Chemical compound C*CCN*C 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- ZQZDMDZWAZDAIM-UHFFFAOYSA-N [1-(chloromethyl)-1,2-dihydrobenzo[e]indol-3-yl]-(5-methoxy-1h-indol-2-yl)methanone Chemical compound C1=CC2=CC=CC=C2C(C(CCl)C2)=C1N2C(=O)C1=CC2=CC(OC)=CC=C2N1 ZQZDMDZWAZDAIM-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004404 heteroalkyl group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- LITLNICSYVUFSG-UHFFFAOYSA-N tert-butyl 1-(chloromethyl)-1,2-dihydrobenzo[e]indole-3-carboxylate Chemical compound C1=CC2=CC=CC=C2C2=C1N(C(=O)OC(C)(C)C)CC2CCl LITLNICSYVUFSG-UHFFFAOYSA-N 0.000 description 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical group CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01301634.0 | 2001-02-22 | ||
| EP01301634 | 2001-02-22 | ||
| PCT/GB2002/000801 WO2002067930A1 (en) | 2001-02-22 | 2002-02-22 | Benz-indole and benzo-quinoline derivatives as prodrugs for tumor treatment |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004522779A JP2004522779A (ja) | 2004-07-29 |
| JP2004522779A5 true JP2004522779A5 (https=) | 2006-01-05 |
| JP4862120B2 JP4862120B2 (ja) | 2012-01-25 |
Family
ID=8181736
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002567297A Expired - Fee Related JP4862120B2 (ja) | 2001-02-22 | 2002-02-22 | 腫瘍治療のためのプロドラッグとしてのベンズ−インドールおよびベンゾ−キノリン誘導体 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US7192977B2 (https=) |
| EP (1) | EP1408960B1 (https=) |
| JP (1) | JP4862120B2 (https=) |
| AT (1) | ATE327750T1 (https=) |
| DE (1) | DE60211905T2 (https=) |
| WO (1) | WO2002067930A1 (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0302094D0 (en) | 2003-01-29 | 2003-02-26 | Pharmagene Lab Ltd | EP4 receptor antagonists |
| GB0324269D0 (en) | 2003-10-16 | 2003-11-19 | Pharmagene Lab Ltd | EP4 receptor antagonists |
| NZ536107A (en) * | 2004-10-22 | 2007-06-29 | Auckland Uniservices Ltd | Nitrobenzindoles and their use in cancer therapy |
| GB0505644D0 (en) | 2005-03-18 | 2005-04-27 | Univ London Pharmacy | Analogues of the azinomycins as anti-tumour agents and as prodrugs |
| US9901567B2 (en) | 2007-08-01 | 2018-02-27 | Syntarga B.V. | Substituted CC-1065 analogs and their conjugates |
| ES2647317T3 (es) * | 2008-11-03 | 2017-12-20 | Syntarga B.V. | Análogos de CC-1065 y sus conjugados |
| PT3056203T (pt) | 2010-04-21 | 2018-02-15 | Syntarga Bv | Conjugados de análogos de cc-1065 e ligantes bifuncionais |
| RU2680404C2 (ru) | 2014-01-10 | 2019-02-21 | Синтон Байофармасьютикалс Б. В. | Способ очистки cys-связанных конъюгатов антитело-лекарственное средство |
| RU2686085C2 (ru) | 2014-01-10 | 2019-04-24 | Синтон Байофармасьютикалс Б. В. | Конъюгаты антитело-лекарственное средство (adc) с дуокармицином, применяемые для лечения рака эндометрия |
| CA2935433C (en) | 2014-01-10 | 2019-04-02 | Synthon Biopharmaceuticals B.V. | Duocarmycin anti-her2 antibody drug conjucates with activity against her2 expressing malignancies |
| CN109020820B (zh) * | 2017-06-08 | 2021-06-25 | 杭州惠诺医药科技有限公司 | 一种6-溴-2-氨基萘的制备方法 |
| JPWO2019004413A1 (ja) * | 2017-06-30 | 2020-05-07 | 東レ株式会社 | インドリン誘導体及びそれを含む細胞毒性剤 |
| CN113292554A (zh) * | 2021-06-25 | 2021-08-24 | 守恒(厦门)医疗科技有限公司 | 二氢萘并[2,1-d]异噁唑酰胺类衍生物及其在抗肿瘤药物的应用 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4413132A (en) | 1980-11-18 | 1983-11-01 | The Upjohn Company | Antibiotic CC-1065 indoline intermediates |
| GB9519490D0 (en) | 1995-09-25 | 1995-11-29 | Melvin William T | Use of a cytochrome P450 enzyme in tumour cells as a marker and target |
| AU727608B2 (en) * | 1995-10-03 | 2000-12-14 | Scripps Research Institute, The | CBI analogs of CC-1065 and the duocarmycins |
| EP0888301B1 (en) * | 1996-03-08 | 2005-08-10 | The Scripps Research Institute | Mcbi analogs of cc-1065 and the duocarmycins |
| US5843937A (en) * | 1996-05-23 | 1998-12-01 | Panorama Research, Inc. | DNA-binding indole derivatives, their prodrugs and immunoconjugates as anticancer agents |
| EP0934269A4 (en) * | 1996-05-31 | 2000-01-12 | Scripps Research Inst | ANALOGS OF CC-1065 AND DUOCARMYCINE |
| AU721037B2 (en) * | 1996-09-12 | 2000-06-22 | Auckland Uniservices Limited | Condensed N-acylindoles as antitumor agents |
| JP4642226B2 (ja) | 1998-02-06 | 2011-03-02 | デ モントフォート ユニヴァーシティ | ヒドロキシル化により活性化されたプロドラッグ |
| US7179921B2 (en) * | 2001-02-22 | 2007-02-20 | School Of Pharmacy, University Of London | Indoline and tetrahydro-quinolines as prodrugs for tumour treatment |
| ES2299560T3 (es) * | 2001-02-22 | 2008-06-01 | University Of Bradford | Derivados de pirrolindol y de pirroloquinolina como profarmacos para el tratamiento de tumores. |
| US6989452B2 (en) * | 2001-05-31 | 2006-01-24 | Medarex, Inc. | Disulfide prodrugs and linkers and stabilizers useful therefor |
| WO2004101767A2 (en) * | 2003-05-13 | 2004-11-25 | The Scripps Research Institute | Cbi analogues of the duocarmycins and cc-1065 |
| JP4806680B2 (ja) * | 2004-05-19 | 2011-11-02 | メダレックス インコーポレイテッド | 自己犠牲リンカー及び薬剤複合体 |
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2002
- 2002-02-22 EP EP02701418A patent/EP1408960B1/en not_active Expired - Lifetime
- 2002-02-22 AT AT02701418T patent/ATE327750T1/de not_active IP Right Cessation
- 2002-02-22 JP JP2002567297A patent/JP4862120B2/ja not_active Expired - Fee Related
- 2002-02-22 WO PCT/GB2002/000801 patent/WO2002067930A1/en not_active Ceased
- 2002-02-22 DE DE60211905T patent/DE60211905T2/de not_active Expired - Lifetime
- 2002-02-22 US US10/468,744 patent/US7192977B2/en not_active Expired - Lifetime
-
2007
- 2007-02-27 US US11/710,899 patent/US8017640B2/en not_active Expired - Fee Related