JP2000516933A - 極めて脂肪親和性のカンプトテシン誘導体 - Google Patents
極めて脂肪親和性のカンプトテシン誘導体Info
- Publication number
- JP2000516933A JP2000516933A JP10510497A JP51049798A JP2000516933A JP 2000516933 A JP2000516933 A JP 2000516933A JP 10510497 A JP10510497 A JP 10510497A JP 51049798 A JP51049798 A JP 51049798A JP 2000516933 A JP2000516933 A JP 2000516933A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- alkyl
- camptothecin
- group
- added
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Cosmetics (AREA)
- Saccharide Compounds (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.式(I): [式中、 −R1は、式−C(O)R2(ここでR2がC1-6アルキル、C2-6アルケニル、 C2-6アルキニル又はアリールを意味する)のアシルを表し、又は C2-8アルケニル若しくはC2-8アルキニルを表すが、これらのそれぞれの基は 1個以上のハロゲン原子、ヒドロキシル基、C1-6アルキル若しくはC1-6アルコ キシ基で置換されることができ、又は ハロ、オキソ(この場合1,2−及び6,7−環二重結合が1つ の2,6− 環二重結合によって置き換えられている)若しくは−S−R3(ここでR3がC1- 6 アルキル、アリール又はハロ−若しくはC1-6アルキル−置換アリールを意味す る)基を表し、又は −S(O)−C1-6アルキル、−OSO2CF3、若しくは−SiR8R9R10、 −R5−SiR8R9R10若しくは−S−R5−SiR8R9R10(ここでR5がC1-6 アルキレン、C2-6アルケニレン若しくはC2-6アルキニレンを、かつR8、R9及 びR10のそれぞれが水素若しくはC1-6アルキルを意味する)を表し、かつ −R11は水素、ヒドロキシル基若しくはヒドロキシル保護基(この保護基はヒド ロキシル基をトリフリル化から保護する)を表す]で表される遊離塩基形状化合 物又はその薬剤として受け入れられる酸添加塩 2.R1がアシル基、ハロ、置換若しくは未置換C2-8アルケニル−若しくはC2- 8 アルキニル−基、−S−R3、−S(O)−C1-6アルキル又は前記のもの又は −SiR8R9R10、−R5−SiR8R9R10又は−S−R5−SiR8R9R10基を 表し、かつ R11が水素又はヒドロキシル基を表すことを特徴とする請求項1記載の化合物 。 3.R8、R9及びR10が全てメチル基を表すことを特徴とする請求項1又は2記 載の化合物。 4.R1が−C1-6−アルキレン−Si(CH3)3又はS−C1-6−アルキレン− Si(CH3)3を表すことを特徴とする請求項3記載の化合物。 5.R1がβ−(トリメチルシリル)エチルを表すことを特徴とする請求項4記 載の化合物。 6.R1が(トリメチルシリル)メチルを表すことを特徴とする請求項4記載の 化合物。 7.R1がトリメチルシリルを表すことを特徴とする請求項4記載の化合物。 8.R1が(トリメチルシリル)エテニルを表すことを特徴とする請求項4記載 の化合物。 9.R1が(トリメチルシリル)エチニルを表すことを特徴とする請求項4記載 の化合物。 10.R1がトリフルオロメチルスルホニルオキシを表すことを特徴とする請求項 1記載の化合物。 11.請求項1乃至10いずれか記載の化合物及び1種以上の薬剤に受け入れられ るぶ形剤、担体又は稀釈剤を含むことを特徴とする薬剤。 12.癌患者治療用の請求項1乃至10いずれか記載の化合物及び請求項11記載 の薬剤。 13.癌患者治療用の薬物の処方のための請求項1乃至10いずれか記載の化合物 の使用。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US2417196P | 1996-08-19 | 1996-08-19 | |
US60/024,171 | 1996-08-19 | ||
PCT/GB1997/002205 WO1998007727A1 (en) | 1996-08-19 | 1997-08-15 | Highly lipophilic camptothecin derivatives |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2000516933A true JP2000516933A (ja) | 2000-12-19 |
JP2000516933A5 JP2000516933A5 (ja) | 2005-04-07 |
JP4364305B2 JP4364305B2 (ja) | 2009-11-18 |
Family
ID=21819224
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP51049798A Expired - Lifetime JP4364305B2 (ja) | 1996-08-19 | 1997-08-15 | 極めて脂肪親和性のカンプトテシン誘導体 |
Country Status (17)
Country | Link |
---|---|
US (3) | US5910491A (ja) |
EP (1) | EP0925301B1 (ja) |
JP (1) | JP4364305B2 (ja) |
KR (1) | KR100516593B1 (ja) |
CN (1) | CN1107678C (ja) |
AT (1) | ATE261974T1 (ja) |
AU (1) | AU718799C (ja) |
BR (1) | BR9711319B1 (ja) |
CA (1) | CA2262745C (ja) |
DE (1) | DE69728152T2 (ja) |
DK (1) | DK0925301T3 (ja) |
ES (1) | ES2214634T3 (ja) |
IL (1) | IL127800A (ja) |
NZ (1) | NZ334240A (ja) |
PT (1) | PT925301E (ja) |
WO (1) | WO1998007727A1 (ja) |
ZA (1) | ZA977437B (ja) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007514779A (ja) * | 2003-12-17 | 2007-06-07 | 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 | カンプトテシン誘導体の製造方法 |
JP2007522083A (ja) * | 2003-06-27 | 2007-08-09 | リサーチ・トライアングル・インスティチュート | 7−置換カンプトテシンおよびカンプトテシン類似体ならびにそれらの調製方法 |
JP2009534389A (ja) * | 2006-04-19 | 2009-09-24 | 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 | 新規な「反転した」ラクトン安定なe−環を有するカンプトテシン類似体並びにその製造及び使用方法 |
JP2011500674A (ja) * | 2007-10-16 | 2011-01-06 | 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 | C10−置換カンプトテシン類似体 |
JP2011500675A (ja) * | 2007-10-16 | 2011-01-06 | 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 |
JP2021526560A (ja) * | 2018-06-12 | 2021-10-07 | マリン バイオメディカル リサーチ インスティテュート オブ チンタオ カンパニー,リミテッドMarine Biomedical Research Institute Of Qingdao Co., Ltd. | カンプトテシン誘導体およびその調製方法並びに用途 |
Families Citing this family (36)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6743917B2 (en) | 1993-06-30 | 2004-06-01 | 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 |
US6136978A (en) * | 1993-06-30 | 2000-10-24 | University Of Pittsburgh | Camptothecin analogs and methods of preparation thereof |
FR2790261B1 (fr) * | 1999-02-26 | 2004-09-10 | Sod Conseils Rech Applic | Nouveaux analogues optiquement purs de la camptothecine et leurs procedes de preparation |
US6407118B1 (en) * | 1996-01-30 | 2002-06-18 | The Stehlin Foundation For Cancer Research | Derivatives of camptothecin and methods of treating cancer using these derivatives |
US6096336A (en) * | 1996-01-30 | 2000-08-01 | The Stehlin Foundation For Cancer Research | Liposomal prodrugs comprising derivatives of camptothecin and methods of treating cancer using these prodrugs |
IT1282673B1 (it) * | 1996-02-23 | 1998-03-31 | Ist Naz Stud Cura Dei Tumori | Derivati della camptotecina e loro uso come agenti antitumorali |
EP0925301B1 (en) * | 1996-08-19 | 2004-03-17 | Bionumerik Pharmaceuticals, Inc. | Highly lipophilic camptothecin derivatives |
US6169080B1 (en) * | 1997-02-13 | 2001-01-02 | Bionumerik Pharmaceuticals, Inc. | Highly lipophilic camptothecin derivatives |
US6057303A (en) * | 1998-10-20 | 2000-05-02 | Bionumerik Pharmaceuticals, Inc. | Highly lipophilic Camptothecin derivatives |
EP1044977B1 (en) * | 1999-03-09 | 2002-05-02 | Sigma-Tau Industrie Farmaceutiche Riunite S.p.A. | Camptothecin derivatives having antitumor activity |
US7105492B2 (en) | 1999-03-09 | 2006-09-12 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. | Camptothecin derivatives having antitumor activity |
US6207832B1 (en) * | 1999-04-09 | 2001-03-27 | University Of Pittsburgh | Camptothecin analogs and methods of preparation thereof |
AU4822500A (en) * | 1999-05-04 | 2000-11-17 | Bionumerik Pharmaceuticals, Inc. | Novel highly lipophilic camptothecin analogs |
US6352996B1 (en) | 1999-08-03 | 2002-03-05 | The Stehlin Foundation For Cancer Research | Liposomal prodrugs comprising derivatives of camptothecin and methods of treating cancer using these prodrugs |
US6228855B1 (en) | 1999-08-03 | 2001-05-08 | The Stehlin Foundation For Cancer Research | Aromatic esters of camptothecins and methods to treat cancers |
EP1229934B1 (en) | 1999-10-01 | 2014-03-05 | Immunogen, Inc. | Compositions and methods for treating cancer using immunoconjugates and chemotherapeutic agents |
US7332550B2 (en) * | 2000-10-06 | 2008-02-19 | Carnegie Mellon University | Stabilization of transition metal complexes for catalysis in diverse environments |
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 |
US6653319B1 (en) | 2001-08-10 | 2003-11-25 | University Of Kentucky Research Foundation | Pharmaceutical formulation for poorly water soluble camptothecin analogues |
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 |
WO2003101998A1 (en) * | 2002-06-03 | 2003-12-11 | California Pacific Medical Center | Nitrogen-based homo-camptothecin derivatives |
US20040034050A1 (en) * | 2002-06-03 | 2004-02-19 | Yang Li-Xi | Homo-camptothecin derivatives |
US6723849B1 (en) * | 2002-10-25 | 2004-04-20 | Bionumerik Pharmaceuticals, Inc. | Process for making camptothecin derivatives |
CN1893892B (zh) * | 2003-12-17 | 2012-03-28 | 比奥纽默里克药物公司 | 喜树碱的药物制剂和制备它们的方法 |
US7030243B1 (en) | 2004-10-28 | 2006-04-18 | Bionumerik Pharmaceuticals, Inc. | Process for making camptothecin derivatives |
US20060094692A1 (en) * | 2004-10-28 | 2006-05-04 | Bionumerik Pharmaceuticals, Inc. | Pharmaceutical formulations of camptothecins and process for making same |
US7875602B2 (en) * | 2005-10-21 | 2011-01-25 | Sutter West Bay Hospitals | Camptothecin derivatives as chemoradiosensitizing agents |
US20110028536A1 (en) * | 2006-08-18 | 2011-02-03 | Gjerset Ruth A | Methods and compositions for topoisomerase i modulated tumor suppression |
JP2010511427A (ja) * | 2006-12-01 | 2010-04-15 | ウェイク・フォレスト・ユニヴァーシティ・ヘルス・サイエンシズ | コラーゲン阻害剤を含む医療デバイス |
US7687496B2 (en) | 2007-10-16 | 2010-03-30 | Bionumerik Pharmaceuticals, Inc. | C7-substituted camptothecin analogs |
US7687497B2 (en) | 2007-10-16 | 2010-03-30 | Bionumerik Pharmaceuticals, Inc. | C10-substituted camptothecin analogs |
US20140073793A1 (en) * | 2012-09-07 | 2014-03-13 | BioNumeric Pharmaceuticals, Inc. | Germanium-containing camptothecin analogues |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3894029A (en) * | 1971-08-26 | 1975-07-08 | Basf Ag | Production of camptothecin and camptothecin-like compounds |
DE2150234A1 (de) * | 1971-10-08 | 1973-04-12 | Basf Ag | Verfahren zur herstellung von camptothecin und camptothecin-derivaten |
DE2534601A1 (de) * | 1975-08-02 | 1977-02-17 | Basf Ag | Verfahren zur herstellung von camptothecin-aehnlichen verbindungen |
US4399282A (en) * | 1979-07-10 | 1983-08-16 | Kabushiki Kaisha Yakult Honsha | Camptothecin derivatives |
US4399276A (en) * | 1981-01-09 | 1983-08-16 | Kabushiki Kaisha Yakult Honsha | 7-Substituted camptothecin derivatives |
US4473692A (en) * | 1981-09-04 | 1984-09-25 | Kabushiki Kaisha Yakult Honsha | Camptothecin derivatives and process for preparing same |
JPS6019790A (ja) * | 1983-07-14 | 1985-01-31 | Yakult Honsha Co Ltd | 新規なカンプトテシン誘導体 |
US5004758A (en) * | 1987-12-01 | 1991-04-02 | Smithkline Beecham Corporation | Water soluble camptothecin analogs useful for inhibiting the growth of animal tumor cells |
JPH0615547B2 (ja) * | 1988-01-20 | 1994-03-02 | 株式会社ヤクルト本社 | 新規なカンプトテシン誘導体 |
US5405963A (en) * | 1993-06-10 | 1995-04-11 | Smithkline Beecham Corporation | Process for asymmetric total synthesis of camptothecin analogues |
US5468754A (en) * | 1994-04-19 | 1995-11-21 | Bionumerik Pharmaceuticals, Inc. | 11,7 substituted camptothecin derivatives and formulations of 11,7 substituted camptothecin derivatives and methods for uses thereof |
US5726181A (en) * | 1995-06-05 | 1998-03-10 | Bionumerik Pharmaceuticals, Inc. | Formulations and compositions of poorly water soluble camptothecin derivatives |
EP0925301B1 (en) * | 1996-08-19 | 2004-03-17 | Bionumerik Pharmaceuticals, Inc. | Highly lipophilic camptothecin derivatives |
-
1997
- 1997-08-15 EP EP97937656A patent/EP0925301B1/en not_active Expired - Lifetime
- 1997-08-15 WO PCT/GB1997/002205 patent/WO1998007727A1/en not_active Application Discontinuation
- 1997-08-15 KR KR10-1999-7001185A patent/KR100516593B1/ko active IP Right Grant
- 1997-08-15 CN CN97197194A patent/CN1107678C/zh not_active Expired - Lifetime
- 1997-08-15 DE DE69728152T patent/DE69728152T2/de not_active Expired - Lifetime
- 1997-08-15 IL IL12780097A patent/IL127800A/xx not_active IP Right Cessation
- 1997-08-15 AU AU40204/97A patent/AU718799C/en not_active Expired
- 1997-08-15 DK DK97937656T patent/DK0925301T3/da active
- 1997-08-15 JP JP51049798A patent/JP4364305B2/ja not_active Expired - Lifetime
- 1997-08-15 BR BRPI9711319-0A patent/BR9711319B1/pt not_active IP Right Cessation
- 1997-08-15 AT AT97937656T patent/ATE261974T1/de active
- 1997-08-15 NZ NZ334240A patent/NZ334240A/xx not_active IP Right Cessation
- 1997-08-15 ES ES97937656T patent/ES2214634T3/es not_active Expired - Lifetime
- 1997-08-15 PT PT97937656T patent/PT925301E/pt unknown
- 1997-08-15 CA CA002262745A patent/CA2262745C/en not_active Expired - Lifetime
- 1997-08-19 ZA ZA977437A patent/ZA977437B/xx unknown
- 1997-08-19 US US08/914,207 patent/US5910491A/en not_active Expired - Lifetime
-
1998
- 1998-10-26 US US09/178,780 patent/US6028078A/en not_active Expired - Lifetime
-
1999
- 1999-12-23 US US09/470,773 patent/US6194579B1/en not_active Expired - Lifetime
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007522083A (ja) * | 2003-06-27 | 2007-08-09 | リサーチ・トライアングル・インスティチュート | 7−置換カンプトテシンおよびカンプトテシン類似体ならびにそれらの調製方法 |
JP2007514779A (ja) * | 2003-12-17 | 2007-06-07 | 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 | カンプトテシン誘導体の製造方法 |
JP4701185B2 (ja) * | 2003-12-17 | 2011-06-15 | 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 | カンプトテシン誘導体の製造方法 |
JP2009534389A (ja) * | 2006-04-19 | 2009-09-24 | 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 | 新規な「反転した」ラクトン安定なe−環を有するカンプトテシン類似体並びにその製造及び使用方法 |
JP2011500674A (ja) * | 2007-10-16 | 2011-01-06 | 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 | C10−置換カンプトテシン類似体 |
JP2011500675A (ja) * | 2007-10-16 | 2011-01-06 | 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 |
JP2021526560A (ja) * | 2018-06-12 | 2021-10-07 | マリン バイオメディカル リサーチ インスティテュート オブ チンタオ カンパニー,リミテッドMarine Biomedical Research Institute Of Qingdao Co., Ltd. | カンプトテシン誘導体およびその調製方法並びに用途 |
JP7485661B2 (ja) | 2018-06-12 | 2024-05-16 | マリン バイオメディカル リサーチ インスティテュート オブ チンタオ カンパニー,リミテッド | カンプトテシン誘導体およびその調製方法並びに用途 |
Also Published As
Publication number | Publication date |
---|---|
JP4364305B2 (ja) | 2009-11-18 |
ZA977437B (en) | 1999-02-19 |
PT925301E (pt) | 2004-08-31 |
DK0925301T3 (da) | 2004-07-12 |
BR9711319A (pt) | 2000-01-18 |
KR20000068135A (ko) | 2000-11-25 |
WO1998007727A1 (en) | 1998-02-26 |
EP0925301A1 (en) | 1999-06-30 |
US5910491A (en) | 1999-06-08 |
US6028078A (en) | 2000-02-22 |
AU718799B2 (en) | 2000-04-20 |
DE69728152D1 (en) | 2004-04-22 |
AU718799C (en) | 2004-02-12 |
IL127800A0 (en) | 1999-10-28 |
ATE261974T1 (de) | 2004-04-15 |
BR9711319B1 (pt) | 2009-08-11 |
ES2214634T3 (es) | 2004-09-16 |
KR100516593B1 (ko) | 2005-09-22 |
NZ334240A (en) | 2000-01-28 |
CN1227559A (zh) | 1999-09-01 |
DE69728152T2 (de) | 2004-08-05 |
CA2262745C (en) | 2006-04-04 |
EP0925301B1 (en) | 2004-03-17 |
AU4020497A (en) | 1998-03-06 |
IL127800A (en) | 2005-11-20 |
US6194579B1 (en) | 2001-02-27 |
CN1107678C (zh) | 2003-05-07 |
CA2262745A1 (en) | 1998-02-26 |
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