JP2002541201A5 - - Google Patents
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- Publication number
- JP2002541201A5 JP2002541201A5 JP2000610479A JP2000610479A JP2002541201A5 JP 2002541201 A5 JP2002541201 A5 JP 2002541201A5 JP 2000610479 A JP2000610479 A JP 2000610479A JP 2000610479 A JP2000610479 A JP 2000610479A JP 2002541201 A5 JP2002541201 A5 JP 2002541201A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- alkyl
- compound according
- compound
- alkynyl
- 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 57
- 125000000217 alkyl group Chemical group 0.000 description 25
- 125000000304 alkynyl group Chemical group 0.000 description 22
- 229910052739 hydrogen Inorganic materials 0.000 description 22
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 19
- 125000003277 amino group Chemical group 0.000 description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 18
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 16
- 125000003545 alkoxy group Chemical group 0.000 description 16
- 125000003118 aryl group Chemical group 0.000 description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 15
- 125000003342 alkenyl group Chemical group 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- 125000004093 cyano group Chemical group *C#N 0.000 description 12
- 229910052731 fluorine Inorganic materials 0.000 description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 12
- 125000005843 halogen group Chemical group 0.000 description 11
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 9
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 9
- 208000032839 leukemia Diseases 0.000 description 8
- 229910052740 iodine Inorganic materials 0.000 description 7
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 125000004450 alkenylene group Chemical group 0.000 description 6
- 125000003282 alkyl amino group Chemical group 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- 125000004419 alkynylene group Chemical group 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 125000004663 dialkyl amino group Chemical group 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 4
- 208000003174 Brain Neoplasms Diseases 0.000 description 4
- 206010006187 Breast cancer Diseases 0.000 description 4
- 208000026310 Breast neoplasm Diseases 0.000 description 4
- 206010028980 Neoplasm Diseases 0.000 description 4
- 201000011510 cancer Diseases 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- 238000007348 radical reaction Methods 0.000 description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 3
- 125000006592 (C2-C3) alkenyl group Chemical group 0.000 description 3
- 125000004423 acyloxy group Chemical group 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000004665 trialkylsilyl group Chemical group 0.000 description 3
- 0 *C(*)([C@](*C(C=C(*)N1CC#C*)=C(C*2)C1=O)O)C2=* Chemical compound *C(*)([C@](*C(C=C(*)N1CC#C*)=C(C*2)C1=O)O)C2=* 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229910017697 MgY Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000010520 demethylation reaction Methods 0.000 description 1
- 238000005828 desilylation reaction Methods 0.000 description 1
- 150000002084 enol ethers Chemical class 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 238000007248 oxidative elimination reaction Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/290,019 US6207832B1 (en) | 1999-04-09 | 1999-04-09 | Camptothecin analogs and methods of preparation thereof |
| US09/290,019 | 1999-04-09 | ||
| PCT/US2000/009401 WO2000061146A1 (en) | 1999-04-09 | 2000-04-07 | Camptothecin analogs and methods of preparation thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002541201A JP2002541201A (ja) | 2002-12-03 |
| JP2002541201A5 true JP2002541201A5 (https=) | 2011-03-03 |
| JP4866505B2 JP4866505B2 (ja) | 2012-02-01 |
Family
ID=23114196
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000610479A Expired - Fee Related JP4866505B2 (ja) | 1999-04-09 | 2000-04-07 | カンプトセシン類似体及びその調製方法 |
Country Status (13)
| Country | Link |
|---|---|
| US (7) | US6207832B1 (https=) |
| EP (1) | EP1173180B1 (https=) |
| JP (1) | JP4866505B2 (https=) |
| KR (1) | KR100717900B1 (https=) |
| CN (2) | CN1319975C (https=) |
| AT (1) | ATE399171T1 (https=) |
| AU (1) | AU781302B2 (https=) |
| CA (1) | CA2369270C (https=) |
| DE (1) | DE60039291D1 (https=) |
| ES (1) | ES2308977T3 (https=) |
| HK (1) | HK1046374B (https=) |
| NZ (1) | NZ514635A (https=) |
| WO (1) | WO2000061146A1 (https=) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2790261B1 (fr) * | 1999-02-26 | 2004-09-10 | Sod Conseils Rech Applic | Nouveaux analogues optiquement purs de la camptothecine et leurs procedes de preparation |
| US6207832B1 (en) | 1999-04-09 | 2001-03-27 | University Of Pittsburgh | Camptothecin analogs and methods of preparation thereof |
| US6629995B1 (en) * | 2000-03-31 | 2003-10-07 | Super Gen, Inc. | Camptothecin conjugates |
| US6350756B1 (en) | 2001-01-18 | 2002-02-26 | California Pacific Medical Center | Camptothecin derivatives |
| US6403604B1 (en) * | 2001-03-01 | 2002-06-11 | California Pacific Medical Center | Nitrogen-based camptothecin derivatives |
| US6855720B2 (en) * | 2001-03-01 | 2005-02-15 | California Pacific Medical Center | Nitrogen-based camptothecin derivatives |
| US6372906B1 (en) | 2001-04-12 | 2002-04-16 | University Of Pittsburgh | Synthesis of silyl camptothecins and silyl homocamptothecins |
| 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 |
| AU2003207369A1 (en) * | 2002-02-18 | 2003-09-04 | Dr. Reddy's Laboratories Limited | A process for the preparation of 10-hydroxy-9-n,n-dimethylaminomethyl-5-(2'-fluoroethoxy)-20(s)-camptothecin hydrochloride |
| WO2003099825A1 (en) * | 2002-05-22 | 2003-12-04 | University Of Pittsburgh | Synthesis of polycyclic quinolines |
| WO2003101998A1 (en) * | 2002-06-03 | 2003-12-11 | California Pacific Medical Center | Nitrogen-based homo-camptothecin derivatives |
| AU2003243397A1 (en) * | 2002-06-03 | 2003-12-19 | California Pacific Medical Center | Homo-camptothecin derivatives |
| AU2003280592B2 (en) * | 2002-10-31 | 2008-12-18 | Nippon Kayaku Kabushiki Kaisha | High-molecular weight derivatives of camptothecins |
| 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 |
| ITRM20040241A1 (it) * | 2004-05-13 | 2004-08-13 | Ist Naz Stud Cura Dei Tumori | Camptotecine coniugate in posizione 20 con antagonisti delle integrine. |
| JP4820758B2 (ja) | 2004-09-22 | 2011-11-24 | 日本化薬株式会社 | 新規ブロック共重合体、ミセル調製物及びそれを有効成分とする抗癌剤 |
| WO2006093994A2 (en) * | 2005-03-02 | 2006-09-08 | New Century Pharmaceuticals | Methods and compositions for increasing the safety and efficacy of albumin-binding drugs |
| US7875602B2 (en) * | 2005-10-21 | 2011-01-25 | Sutter West Bay Hospitals | Camptothecin derivatives as chemoradiosensitizing agents |
| US8323669B2 (en) | 2006-03-28 | 2012-12-04 | Nippon Kayaku Kabushiki Kaisha | Polymer conjugate of taxane |
| RU2447095C2 (ru) | 2006-05-18 | 2012-04-10 | Ниппон Каяку Кабусики Кайся | Высокомолекулярный конъюгат подофиллотоксинов |
| JP5548364B2 (ja) * | 2006-10-03 | 2014-07-16 | 日本化薬株式会社 | レゾルシノール誘導体の高分子結合体 |
| US8334364B2 (en) | 2006-11-06 | 2012-12-18 | Nipon Kayaku Kabushiki Kaisha | High-molecular weight derivative of nucleic acid antimetabolite |
| JP5548365B2 (ja) | 2006-11-08 | 2014-07-16 | 日本化薬株式会社 | 核酸系代謝拮抗剤の高分子誘導体 |
| JP5349318B2 (ja) | 2007-09-28 | 2013-11-20 | 日本化薬株式会社 | ステロイド類の高分子結合体 |
| CN101977631A (zh) * | 2008-03-18 | 2011-02-16 | 日本化药株式会社 | 生理活性物质的高分子量偶联物 |
| JP5366940B2 (ja) | 2008-05-08 | 2013-12-11 | 日本化薬株式会社 | 葉酸若しくは葉酸誘導体の高分子結合体 |
| JP5544357B2 (ja) | 2009-05-15 | 2014-07-09 | 日本化薬株式会社 | 水酸基を有する生理活性物質の高分子結合体 |
| KR20140024833A (ko) | 2010-11-17 | 2014-03-03 | 니폰 가야꾸 가부시끼가이샤 | 신규한 시티딘계 대사길항제의 고분자 유도체 |
| CN103874722B (zh) | 2011-09-11 | 2016-06-29 | 日本化药株式会社 | 嵌段共聚物的制造方法 |
| CA3241157A1 (en) * | 2021-12-16 | 2023-06-22 | Wei Zhou | Camptothecin compound and conjugate thereof |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5428166A (en) * | 1992-06-18 | 1995-06-27 | North Carolina State University | Method of making asymmetric de ring intermediates for the synthesis of camptothecin and camptothecin analogs |
| US5405963A (en) | 1993-06-10 | 1995-04-11 | Smithkline Beecham Corporation | Process for asymmetric total synthesis of camptothecin analogues |
| US6136978A (en) | 1993-06-30 | 2000-10-24 | University Of Pittsburgh | Camptothecin analogs and methods of preparation thereof |
| US6150343A (en) * | 1993-06-30 | 2000-11-21 | University Of Pittsburgh | Camptothecin analogs and methods of preparation thereof |
| US6211371B1 (en) * | 1993-06-30 | 2001-04-03 | University Of Pittsburgh | Intermediates in the synthesis of camptothecin and related compounds and synthesis thereof |
| US5744605A (en) * | 1993-06-30 | 1998-04-28 | University Of Pittsburgh | Intermediates in the synthesis of (+) camptothecin and related compounds and synthesis thereof |
| US5491237A (en) * | 1994-05-03 | 1996-02-13 | Glaxo Wellcome Inc. | Intermediates in pharmaceutical camptothecin preparation |
| US5935967A (en) | 1995-06-05 | 1999-08-10 | Bionumerik Pharmaceuticals, Inc. | Pharmaceutical formulations of highly lipophilic camptothecin derivatives |
| FR2790261B1 (fr) * | 1999-02-26 | 2004-09-10 | Sod Conseils Rech Applic | Nouveaux analogues optiquement purs de la camptothecine et leurs procedes de preparation |
| FR2757514B1 (fr) | 1996-12-20 | 1999-02-12 | Sod Conseils Rech Applic | Nouveaux analogues de la camptothecine, des procedes de preparation, leur application comme medicaments et les compositions pharmaceutiques les contenant |
| DE69623961T2 (de) | 1995-06-21 | 2003-05-08 | Societe De Conseils De Recherches Et D'applications Scientifiques (S.C.R.A.S.), Paris | Camptothecinanaloge, verfahren zur ihrer herstellung, ihre verwendungals arzneimittel und diese enthaltende pharmazeutische zusammenfassungen |
| GB9512670D0 (en) * | 1995-06-21 | 1995-08-23 | Sod Conseils Rech Applic | Camptothecin analogues |
| FR2768431B1 (fr) | 1997-08-29 | 2000-03-24 | Sod Conseils Rech Applic | Nouveaux analogues optiquement purs de la camptothecine, nouvel intermediaire de synthese optiquement pur et son procede de preparation |
| KR100516593B1 (ko) | 1996-08-19 | 2005-09-22 | 바이오누머릭 파마슈티칼스, 인코포레이티드 | 고 친유성 캠프토테신 유도체 |
| UA57757C2 (uk) * | 1996-12-20 | 2003-07-15 | Сос'Єте Де Консей Де Решерш Е Даплікасьон С'Єнтіфік (С.К.Р.А.С.) | Аналоги камптотецину, спосіб їх отримання (варіанти) і фармацевтична композиція |
| ES2262223T3 (es) | 1997-02-14 | 2006-11-16 | Bionumerik Pharmaceuticals, Inc. | Derivados de camptotecina altamente lipofilos. |
| WO1999006310A2 (en) * | 1997-08-04 | 1999-02-11 | Abb Power T & D Company Inc. | Method and apparatus for manufacturing a variable insulated helically wound electrical coil |
| US6057303A (en) | 1998-10-20 | 2000-05-02 | Bionumerik Pharmaceuticals, Inc. | Highly lipophilic Camptothecin derivatives |
| US6207832B1 (en) * | 1999-04-09 | 2001-03-27 | University Of Pittsburgh | Camptothecin analogs and methods of preparation thereof |
| US6250342B1 (en) * | 1999-09-02 | 2001-06-26 | David Lonardelli | Cv joint boot clamp tightening tool |
-
1999
- 1999-04-09 US US09/290,019 patent/US6207832B1/en not_active Expired - Fee Related
-
2000
- 2000-04-07 WO PCT/US2000/009401 patent/WO2000061146A1/en not_active Ceased
- 2000-04-07 NZ NZ514635A patent/NZ514635A/xx not_active IP Right Cessation
- 2000-04-07 CN CNB008086966A patent/CN1319975C/zh not_active Expired - Fee Related
- 2000-04-07 JP JP2000610479A patent/JP4866505B2/ja not_active Expired - Fee Related
- 2000-04-07 EP EP00921919A patent/EP1173180B1/en not_active Expired - Lifetime
- 2000-04-07 AU AU42177/00A patent/AU781302B2/en not_active Ceased
- 2000-04-07 ES ES00921919T patent/ES2308977T3/es not_active Expired - Lifetime
- 2000-04-07 CA CA2369270A patent/CA2369270C/en not_active Expired - Fee Related
- 2000-04-07 CN CNA2007101049994A patent/CN101058579A/zh active Pending
- 2000-04-07 KR KR1020017012901A patent/KR100717900B1/ko not_active Expired - Fee Related
- 2000-04-07 DE DE60039291T patent/DE60039291D1/de not_active Expired - Lifetime
- 2000-04-07 AT AT00921919T patent/ATE399171T1/de active
- 2000-04-07 HK HK02107997.6A patent/HK1046374B/zh not_active IP Right Cessation
- 2000-11-30 US US09/728,031 patent/US6410731B2/en not_active Expired - Fee Related
-
2002
- 2002-06-06 US US10/164,326 patent/US6809103B2/en not_active Expired - Fee Related
-
2004
- 2004-08-16 US US10/919,068 patent/US7220860B2/en not_active Expired - Fee Related
-
2007
- 2007-05-22 US US11/805,169 patent/US7538220B2/en not_active Expired - Fee Related
-
2009
- 2009-04-16 US US12/425,364 patent/US7982041B2/en not_active Expired - Fee Related
-
2011
- 2011-07-05 US US13/176,259 patent/US20120136153A1/en not_active Abandoned
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