JP2002532505A5 - - Google Patents
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- Publication number
- JP2002532505A5 JP2002532505A5 JP2000588183A JP2000588183A JP2002532505A5 JP 2002532505 A5 JP2002532505 A5 JP 2002532505A5 JP 2000588183 A JP2000588183 A JP 2000588183A JP 2000588183 A JP2000588183 A JP 2000588183A JP 2002532505 A5 JP2002532505 A5 JP 2002532505A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- amino
- alkyl
- hydroxy
- independently
- 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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- 150000001875 compounds Chemical class 0.000 description 38
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 26
- 238000000034 method Methods 0.000 description 21
- 125000003277 amino group Chemical group 0.000 description 20
- 125000004093 cyano group Chemical group *C#N 0.000 description 20
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 20
- 125000003545 alkoxy group Chemical group 0.000 description 18
- 125000000217 alkyl group Chemical group 0.000 description 16
- -1 aryl isonitrile Chemical class 0.000 description 13
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- 125000000304 alkynyl group Chemical group 0.000 description 11
- 125000004663 dialkyl amino group Chemical group 0.000 description 11
- 125000005843 halogen group Chemical group 0.000 description 10
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 8
- 125000003282 alkyl amino group Chemical group 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 125000004450 alkenylene group Chemical group 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 229910052736 halogen Inorganic materials 0.000 description 7
- 150000002367 halogens Chemical class 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 239000008194 pharmaceutical composition Substances 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- 125000004419 alkynylene group Chemical group 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 4
- 0 *c(cc1*)c(*)c(c(*)c2CN34)c1nc2C3=CC([C@@](C(OC1)=O)(O)I)=C1C4=O Chemical compound *c(cc1*)c(*)c(c(*)c2CN34)c1nc2C3=CC([C@@](C(OC1)=O)(O)I)=C1C4=O 0.000 description 4
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 208000032839 leukemia Diseases 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 3
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 description 3
- 125000006592 (C2-C3) alkenyl group Chemical group 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 125000004423 acyloxy group Chemical group 0.000 description 3
- 125000004103 aminoalkyl group Chemical group 0.000 description 3
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000004665 trialkylsilyl group Chemical group 0.000 description 3
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 description 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 2
- 125000006593 (C2-C3) alkynyl group Chemical group 0.000 description 2
- 208000003174 Brain Neoplasms Diseases 0.000 description 2
- 206010006187 Breast cancer Diseases 0.000 description 2
- 208000026310 Breast neoplasm Diseases 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/212,178 US6136978A (en) | 1993-06-30 | 1998-12-15 | Camptothecin analogs and methods of preparation thereof |
| US09/212,178 | 1998-12-15 | ||
| PCT/US1999/029937 WO2000035924A1 (en) | 1998-12-15 | 1999-12-15 | Camptothecin analogs and methods of preparation thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002532505A JP2002532505A (ja) | 2002-10-02 |
| JP2002532505A5 true JP2002532505A5 (enExample) | 2007-02-15 |
| JP4638987B2 JP4638987B2 (ja) | 2011-02-23 |
Family
ID=22789889
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000588183A Expired - Fee Related JP4638987B2 (ja) | 1998-12-15 | 1999-12-15 | カンプトテシン類似体及びその調製方法 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6136978A (enExample) |
| EP (1) | EP1140948A4 (enExample) |
| JP (1) | JP4638987B2 (enExample) |
| KR (1) | KR100750693B1 (enExample) |
| CN (1) | CN1177850C (enExample) |
| AU (1) | AU777786B2 (enExample) |
| CA (1) | CA2353822C (enExample) |
| HK (1) | HK1044156B (enExample) |
| NZ (1) | NZ512210A (enExample) |
| WO (1) | WO2000035924A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6150343A (en) * | 1993-06-30 | 2000-11-21 | University Of Pittsburgh | Camptothecin analogs and methods of preparation thereof |
| US6207832B1 (en) | 1999-04-09 | 2001-03-27 | University Of Pittsburgh | Camptothecin analogs and methods of preparation thereof |
| US6497896B2 (en) | 2001-02-12 | 2002-12-24 | Supergen, Inc. | Method for administering camptothecins via injection of a pharmaceutical composition comprising microdroplets containing a camptothecin |
| US6509027B2 (en) | 2001-02-12 | 2003-01-21 | Supergen, Inc. | Injectable pharmaceutical composition comprising coated particles of camptothecin |
| US6723853B2 (en) | 2001-08-27 | 2004-04-20 | University Of Pittsburgh | Intermediates and methods of preparation of intermediates in the enantiomeric synthesis of (20R)homocamptothecins and the enantiomeric synthesis of (20R)homocamptothecins |
| KR20040048995A (ko) | 2001-10-25 | 2004-06-10 | 다케다 야쿠힌 고교 가부시키가이샤 | 퀴놀린 화합물 |
| US7064206B1 (en) | 2003-05-12 | 2006-06-20 | University Of Kentucky Research Foundation | Highly lipophilic camptothecin intermediates and prodrugs and methods of preparation thereof |
| US7064202B1 (en) | 2003-05-12 | 2006-06-20 | University Of Kentucky Research Foundation | Camptothecin intermediates and prodrugs and methods of preparation thereof |
| CA2548543C (en) * | 2003-12-17 | 2012-01-03 | Bionumerik Pharmaceuticals, Inc. | Process for making camptothecin derivatives |
| US7654501B2 (en) * | 2007-06-06 | 2010-02-02 | Matthews Stewart D | Vehicle parking assistance device and method for use of same |
| US7687497B2 (en) * | 2007-10-16 | 2010-03-30 | Bionumerik Pharmaceuticals, Inc. | C10-substituted camptothecin analogs |
| HUE031374T2 (en) | 2007-10-16 | 2017-07-28 | Bionumerik Pharmaceuticals Inc | C10-substituted camptothecin analogs |
| JP5467046B2 (ja) * | 2007-10-16 | 2014-04-09 | バイオニューメリック・ファーマスーティカルズ・インコーポレイテッド | Ｃ７−置換カンプトテシン類似体 |
| US8569265B2 (en) * | 2011-05-06 | 2013-10-29 | Bionumerik Pharmaceuticals, Inc. | Deuterated analogs of (4S)-4-ethyl-4-hydroxy-11-[2- (trimethylsilyl)ethyl]-1H-pyrano[3′, 4′:6,7] indolizino [1,2-b]quinoline-3,14(4H, 12H)-dione and methods of use thereof |
| US8722886B1 (en) * | 2012-11-13 | 2014-05-13 | Bionumerik Pharmaceuticals, Inc. | Methods for the total chemical synthesis of enantiomerically-pure 7-(2′-trimethylsilyl)ethyl camptothecin |
| EP3209666B1 (en) * | 2014-10-22 | 2019-08-21 | Vivacitas Oncology Inc. | Methods and systems for camptothecin analog synthesis |
| CN107964257B (zh) * | 2016-10-20 | 2021-07-09 | 香港理工大学深圳研究院 | 喹啉鎓离子骨架结构有机染料化合物及其制备方法和应用 |
| CA3241157A1 (en) * | 2021-12-16 | 2023-06-22 | Wei Zhou | Camptothecin compound and conjugate thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5405963A (en) * | 1993-06-10 | 1995-04-11 | Smithkline Beecham Corporation | Process for asymmetric total synthesis of camptothecin analogues |
| US6150343A (en) * | 1993-06-30 | 2000-11-21 | University Of Pittsburgh | Camptothecin analogs and methods of preparation thereof |
| US5744605A (en) * | 1993-06-30 | 1998-04-28 | University Of Pittsburgh | Intermediates in the synthesis of (+) camptothecin and related compounds and synthesis thereof |
| JPH09123996A (ja) * | 1995-10-30 | 1997-05-13 | Sanshin Ind Co Ltd | 船外機のシフト駆動機構 |
| DE69728152T2 (de) * | 1996-08-19 | 2004-08-05 | Bionumerik Pharmaceuticals, Inc., San Antonio | Hoch-lipophile campothecin-derivate |
| DK1017675T3 (da) * | 1997-02-14 | 2006-10-16 | Bionumerik Pharmaceuticals Inc | Stærkt lipofile camptothecinderivater |
-
1998
- 1998-12-15 US US09/212,178 patent/US6136978A/en not_active Expired - Fee Related
-
1999
- 1999-12-15 CN CNB998157686A patent/CN1177850C/zh not_active Expired - Fee Related
- 1999-12-15 KR KR1020017007539A patent/KR100750693B1/ko not_active Expired - Fee Related
- 1999-12-15 NZ NZ51221099A patent/NZ512210A/xx not_active IP Right Cessation
- 1999-12-15 WO PCT/US1999/029937 patent/WO2000035924A1/en not_active Ceased
- 1999-12-15 AU AU31236/00A patent/AU777786B2/en not_active Ceased
- 1999-12-15 EP EP99965287A patent/EP1140948A4/en not_active Withdrawn
- 1999-12-15 HK HK02105702.6A patent/HK1044156B/zh not_active IP Right Cessation
- 1999-12-15 CA CA2353822A patent/CA2353822C/en not_active Expired - Fee Related
- 1999-12-15 JP JP2000588183A patent/JP4638987B2/ja not_active Expired - Fee Related