JP2002541201A5 - - Google Patents
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- 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 (cg-RX-API-DMAC10.html) | 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 (cg-RX-API-DMAC10.html) |
| EP (1) | EP1173180B1 (cg-RX-API-DMAC10.html) |
| JP (1) | JP4866505B2 (cg-RX-API-DMAC10.html) |
| KR (1) | KR100717900B1 (cg-RX-API-DMAC10.html) |
| CN (2) | CN1319975C (cg-RX-API-DMAC10.html) |
| AT (1) | ATE399171T1 (cg-RX-API-DMAC10.html) |
| AU (1) | AU781302B2 (cg-RX-API-DMAC10.html) |
| CA (1) | CA2369270C (cg-RX-API-DMAC10.html) |
| DE (1) | DE60039291D1 (cg-RX-API-DMAC10.html) |
| ES (1) | ES2308977T3 (cg-RX-API-DMAC10.html) |
| HK (1) | HK1046374B (cg-RX-API-DMAC10.html) |
| NZ (1) | NZ514635A (cg-RX-API-DMAC10.html) |
| WO (1) | WO2000061146A1 (cg-RX-API-DMAC10.html) |
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 |
| US6855720B2 (en) * | 2001-03-01 | 2005-02-15 | California Pacific Medical Center | Nitrogen-based camptothecin derivatives |
| US6403604B1 (en) * | 2001-03-01 | 2002-06-11 | 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 |
| WO2003068778A1 (en) * | 2002-02-18 | 2003-08-21 | 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 |
| AU2003243397A1 (en) * | 2002-06-03 | 2003-12-19 | California Pacific Medical Center | Homo-camptothecin derivatives |
| US6933302B2 (en) * | 2002-06-03 | 2005-08-23 | California Pacific Medical Center | Nitrogen-based homo-camptothecin derivatives |
| CA2502870C (en) * | 2002-10-31 | 2011-07-26 | Nippon Kayaku Kabushiki Kaisha | High-molecular weight derivatives of camptothecins |
| US7064202B1 (en) | 2003-05-12 | 2006-06-20 | University Of Kentucky Research Foundation | Camptothecin intermediates and prodrugs and methods of preparation thereof |
| US7064206B1 (en) | 2003-05-12 | 2006-06-20 | University Of Kentucky Research Foundation | Highly lipophilic 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. |
| CN101023119B (zh) * | 2004-09-22 | 2010-05-05 | 日本化药株式会社 | 新型嵌段共聚物，胶束制剂以及含胶束制剂为活性组分的抗癌剂 |
| JP5030799B2 (ja) * | 2005-03-02 | 2012-09-19 | ニュー センチュリー ファーマシューティカルズ インコーポレイテッド | アルブミン結合性薬物の安全性および効力を増大させる方法および組成物 |
| US7875602B2 (en) * | 2005-10-21 | 2011-01-25 | Sutter West Bay Hospitals | Camptothecin derivatives as chemoradiosensitizing agents |
| KR20080106254A (ko) | 2006-03-28 | 2008-12-04 | 니폰 가야꾸 가부시끼가이샤 | 탁산류의 고분자 결합체 |
| CA2652656A1 (en) | 2006-05-18 | 2007-11-29 | Nippon Kayaku Kabushiki Kaisha | High-molecular weight conjugate of podophyllotoxins |
| CA2664852A1 (en) * | 2006-10-03 | 2008-04-10 | Nippon Kayaku Kabushiki Kaisha | High-molecular weight conjugate of resorcinol derivatives |
| EP2080779B1 (en) | 2006-11-06 | 2016-05-18 | Nippon Kayaku Kabushiki Kaisha | Polymeric derivative of nucleic acid metabolic antagonist |
| EP2090607B1 (en) | 2006-11-08 | 2015-05-20 | Nippon Kayaku Kabushiki Kaisha | Polymeric derivative of nucleic acid metabolic antagonist |
| US8703878B2 (en) * | 2007-09-28 | 2014-04-22 | Nippon Kayaku Kabushiki Kaisha | High-molecular weight conjugate of steroids |
| KR101589582B1 (ko) * | 2008-03-18 | 2016-01-28 | 니폰 가야꾸 가부시끼가이샤 | 생리활성물질의 고분자량 결합체 |
| 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 |
| JP5856069B2 (ja) | 2010-11-17 | 2016-02-09 | 日本化薬株式会社 | 新規なシチジン系代謝拮抗剤の高分子誘導体 |
| JP5711378B2 (ja) | 2011-09-11 | 2015-04-30 | 日本化薬株式会社 | ブロック共重合体の製造方法 |
| CN118414339A (zh) * | 2021-12-16 | 2024-07-30 | 迈威(上海)生物科技股份有限公司 | 一种喜树碱类化合物及其偶联物 |
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 |
| 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 |
| US6136978A (en) | 1993-06-30 | 2000-10-24 | 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 |
| 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 |
| GB9512670D0 (en) * | 1995-06-21 | 1995-08-23 | Sod Conseils Rech Applic | Camptothecin analogues |
| DE69635560T2 (de) | 1995-06-21 | 2006-08-17 | Société de Conseils de Recherches et D'Applications Scientifiques (S.C.R.A.S.) | Camptothecinanaloge, Verfahren zur ihrer Herstellung, ihre Verwendung als Arzneimittel und diese enthaltende pharmazeutische Zusammensetzungen |
| FR2790261B1 (fr) * | 1999-02-26 | 2004-09-10 | Sod Conseils Rech Applic | Nouveaux analogues optiquement purs de la camptothecine et leurs procedes de preparation |
| 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 |
| 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 |
| DE69728152T2 (de) | 1996-08-19 | 2004-08-05 | Bionumerik Pharmaceuticals, Inc., San Antonio | Hoch-lipophile campothecin-derivate |
| 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 |
| DE69834923T2 (de) | 1997-02-14 | 2006-10-19 | Bionumerik Pharmaceuticals, Inc., San Antonio | Hochgradig lipophile camptothecin-derivate |
| 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 AT AT00921919T patent/ATE399171T1/de active
- 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 HK HK02107997.6A patent/HK1046374B/zh not_active IP Right Cessation
- 2000-04-07 KR KR1020017012901A patent/KR100717900B1/ko not_active Expired - Fee Related
- 2000-04-07 CN CNB008086966A patent/CN1319975C/zh not_active Expired - Fee Related
- 2000-04-07 CN CNA2007101049994A patent/CN101058579A/zh active Pending
- 2000-04-07 ES ES00921919T patent/ES2308977T3/es not_active Expired - Lifetime
- 2000-04-07 JP JP2000610479A patent/JP4866505B2/ja not_active Expired - Fee Related
- 2000-04-07 CA CA2369270A patent/CA2369270C/en not_active Expired - Fee Related
- 2000-04-07 AU AU42177/00A patent/AU781302B2/en not_active Ceased
- 2000-04-07 EP EP00921919A patent/EP1173180B1/en not_active Expired - Lifetime
- 2000-04-07 DE DE60039291T patent/DE60039291D1/de not_active Expired - Lifetime
- 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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