DE69732421D1 - Verfahren zur hertellung von paclitaxel - Google Patents
Verfahren zur hertellung von paclitaxelInfo
- Publication number
- DE69732421D1 DE69732421D1 DE69732421T DE69732421T DE69732421D1 DE 69732421 D1 DE69732421 D1 DE 69732421D1 DE 69732421 T DE69732421 T DE 69732421T DE 69732421 T DE69732421 T DE 69732421T DE 69732421 D1 DE69732421 D1 DE 69732421D1
- Authority
- DE
- Germany
- Prior art keywords
- protecting group
- benzyl
- hydrogen
- side chain
- cbz
- 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.)
- Expired - Lifetime
Links
- 229930012538 Paclitaxel Natural products 0.000 title abstract 2
- 229960001592 paclitaxel Drugs 0.000 title abstract 2
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 title abstract 2
- 125000006239 protecting group Chemical group 0.000 abstract 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 abstract 2
- OVMSOCFBDVBLFW-VHLOTGQHSA-N 5beta,20-epoxy-1,7beta,13alpha-trihydroxy-9-oxotax-11-ene-2alpha,4alpha,10beta-triyl 4,10-diacetate 2-benzoate Chemical compound O([C@@H]1[C@@]2(C[C@H](O)C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)O)C(=O)C1=CC=CC=C1 OVMSOCFBDVBLFW-VHLOTGQHSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- RZARFIRJROUVLM-JGVFFNPUSA-N (2r,3s)-3-azaniumyl-2-hydroxy-3-phenylpropanoate Chemical group [O-]C(=O)[C@H](O)[C@@H]([NH3+])C1=CC=CC=C1 RZARFIRJROUVLM-JGVFFNPUSA-N 0.000 abstract 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229930014667 baccatin III Natural products 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 abstract 1
- -1 benzyloxymethyl Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/14—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
-
- 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)
- Epoxy Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/719,488 US5750737A (en) | 1996-09-25 | 1996-09-25 | Method for paclitaxel synthesis |
| PCT/US1997/017230 WO1998013360A1 (en) | 1996-09-25 | 1997-09-25 | Method for paclitaxel synthesis |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE69732421D1 true DE69732421D1 (de) | 2005-03-10 |
Family
ID=24890263
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69732421T Expired - Lifetime DE69732421D1 (de) | 1996-09-25 | 1997-09-25 | Verfahren zur hertellung von paclitaxel |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US5750737A (enExample) |
| EP (1) | EP0935596B1 (enExample) |
| JP (1) | JP2001501613A (enExample) |
| CN (2) | CN1097586C (enExample) |
| AT (1) | ATE288427T1 (enExample) |
| AU (1) | AU736591B2 (enExample) |
| CA (1) | CA2266892C (enExample) |
| DE (1) | DE69732421D1 (enExample) |
| IL (1) | IL129100A (enExample) |
| WO (1) | WO1998013360A1 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5973170A (en) * | 1996-09-25 | 1999-10-26 | Napro Biotherapuetics, Inc. | C-7 metal alkoxides of baccatin III |
| US6448417B1 (en) * | 1998-05-01 | 2002-09-10 | Napro Biotherapeutics, Inc. | Methods and useful intermediates for paclitaxel synthesis from C-7, C-10 di-cbz 10-deacetylbaccatin III |
| US6002025A (en) * | 1999-02-24 | 1999-12-14 | Bcm Developement Inc. | Method for the purification of taxanes |
| US6136999A (en) * | 1999-06-21 | 2000-10-24 | Napro Biotherapeutics, Inc. | C-2 hydroxyl protected-n-acyl (2R,3S)-3-phenylisoserine substituted phenyl activated esters and method for production thereof |
| US6143902A (en) * | 1999-06-21 | 2000-11-07 | Napro Biotherapeutics, Inc. | C-2 hydroxyl protected-N-acyl (2R,3S)-3-phenylisoserine N-imido activated esters and method for production thereof |
| EP1192126A1 (en) * | 1999-06-21 | 2002-04-03 | Napro Biotherapeutics, Inc. | C-2 hydroxyl protected-n-acyl(2r,3s)-3-phenylisoserine activated esters and methods for production thereof |
| US20040115134A1 (en) * | 1999-06-22 | 2004-06-17 | Elan Pharma International Ltd. | Novel nifedipine compositions |
| US6452024B1 (en) | 2000-02-22 | 2002-09-17 | Chaichem Pharmaceuticals International | Process for extraction and purification of paclitaxel from natural sources |
| US6358996B1 (en) | 2000-06-09 | 2002-03-19 | Napro Biotherapeutics, Inc. | Stable isotope labeling of paclitaxel |
| US6825166B2 (en) * | 2001-03-23 | 2004-11-30 | Tapestry Pharmaceuticals, Inc. | Molecular conjugates for use in treatment of cancer |
| US6452025B1 (en) | 2001-04-25 | 2002-09-17 | Napro Biotherapeutics, Inc. | Three-step conversion of protected taxane ester to paclitaxel |
| US6479679B1 (en) | 2001-04-25 | 2002-11-12 | Napro Biotherapeutics, Inc. | Two-step conversion of protected taxane ester to paclitaxel |
| US6653501B2 (en) | 2001-06-27 | 2003-11-25 | Napro Biotherapeutics, Inc. | Chiral resolution method for producing compounds useful in the synthesis of taxanes |
| CA2479665C (en) * | 2002-03-20 | 2011-08-30 | Elan Pharma International Ltd. | Nanoparticulate compositions of angiogenesis inhibitors |
| US6759539B1 (en) | 2003-02-27 | 2004-07-06 | Chaichem Pharmaceuticals International | Process for isolation and purification of paclitaxel from natural sources |
| US20050272807A1 (en) * | 2004-06-04 | 2005-12-08 | Phytogen Life Sciences Inc. | Semi-synthesis of taxane intermediates and their conversion to paclitaxel and docetaxel |
| JP2009521435A (ja) * | 2005-12-21 | 2009-06-04 | タペストリー ファーマシューティカルズ インコーポレーテッド | タキサンを形成するための新規化合物および方法ならびにその使用 |
| US20090306400A1 (en) * | 2006-03-27 | 2009-12-10 | Henri John T | Convergent process for the synthesis of taxane derivatives. |
| US20100137221A1 (en) * | 2007-02-27 | 2010-06-03 | University Utah Research Foundation | Peptides that interact with topoisomerase i and methods thereof |
| TW201127384A (en) * | 2009-11-18 | 2011-08-16 | Nerviano Medical Sciences Srl | Therapeutic combination comprising a Cdc7 inhibitor and an antineoplastic agent |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US34277A (en) * | 1862-01-28 | Improvement in lamps | ||
| FR2601676B1 (fr) * | 1986-07-17 | 1988-09-23 | Rhone Poulenc Sante | Procede de preparation du taxol et du desacetyl-10 taxol |
| FR2601675B1 (fr) * | 1986-07-17 | 1988-09-23 | Rhone Poulenc Sante | Derives du taxol, leur preparation et les compositions pharmaceutiques qui les contiennent |
| USRE34277E (en) * | 1988-04-06 | 1993-06-08 | Centre National De La Recherche Scientifique | Process for preparing taxol |
| FR2629818B1 (fr) * | 1988-04-06 | 1990-11-16 | Centre Nat Rech Scient | Procede de preparation du taxol |
| FR2629819B1 (fr) * | 1988-04-06 | 1990-11-16 | Rhone Poulenc Sante | Procede de preparation de derives de la baccatine iii et de la desacetyl-10 baccatine iii |
| US4960790A (en) * | 1989-03-09 | 1990-10-02 | University Of Kansas | Derivatives of taxol, pharmaceutical compositions thereof and methods for the preparation thereof |
| US5175315A (en) * | 1989-05-31 | 1992-12-29 | Florida State University | Method for preparation of taxol using β-lactam |
| US5136060A (en) * | 1989-11-14 | 1992-08-04 | Florida State University | Method for preparation of taxol using an oxazinone |
| US5015744A (en) * | 1989-11-14 | 1991-05-14 | Florida State University | Method for preparation of taxol using an oxazinone |
| FR2658513B1 (fr) * | 1990-02-21 | 1994-02-04 | Rhone Poulenc Sante | Procede de preparation de l'acide cis-beta-phenylglycidique-(2r,3r). |
| FR2680506B1 (fr) * | 1991-08-19 | 1994-09-02 | Rhone Poulenc Rorer Sa | Procede de preparation de derives de la beta-phenylisoserine et leur utilisation. |
| US5229526A (en) * | 1991-09-23 | 1993-07-20 | Florida State University | Metal alkoxides |
| US5399726A (en) * | 1993-01-29 | 1995-03-21 | Florida State University | Process for the preparation of baccatin III analogs bearing new C2 and C4 functional groups |
| FR2687150B1 (fr) * | 1992-02-07 | 1995-04-28 | Rhone Poulenc Rorer Sa | Procede de preparation de derives du taxane. |
| FR2687151B1 (fr) * | 1992-02-07 | 1994-03-25 | Rhone Poulenc Rorer Sa | Nouveaux derives de la baccatine iii et de la desacetyl-10 baccatine iii, leur preparation et les compositions pharmaceutiques qui les contiennent. |
| US5948919A (en) * | 1993-02-05 | 1999-09-07 | Napro Biotherapeutics, Inc. | Paclitaxel synthesis from precursor compounds and methods of producing the same |
| JP3031715B2 (ja) * | 1993-02-05 | 2000-04-10 | ブリン モーアー カレッジ | 様々なａ環側鎖を有するタキソール、類似体及び中間体の合成 |
-
1996
- 1996-09-25 US US08/719,488 patent/US5750737A/en not_active Expired - Lifetime
-
1997
- 1997-09-02 US US08/922,684 patent/US6133462A/en not_active Expired - Fee Related
- 1997-09-25 CA CA002266892A patent/CA2266892C/en not_active Expired - Fee Related
- 1997-09-25 DE DE69732421T patent/DE69732421D1/de not_active Expired - Lifetime
- 1997-09-25 IL IL12910097A patent/IL129100A/en not_active IP Right Cessation
- 1997-09-25 AU AU45021/97A patent/AU736591B2/en not_active Expired
- 1997-09-25 WO PCT/US1997/017230 patent/WO1998013360A1/en not_active Ceased
- 1997-09-25 EP EP97943583A patent/EP0935596B1/en not_active Expired - Lifetime
- 1997-09-25 JP JP10515906A patent/JP2001501613A/ja not_active Ceased
- 1997-09-25 AT AT97943583T patent/ATE288427T1/de not_active IP Right Cessation
- 1997-09-25 CN CN97198130A patent/CN1097586C/zh not_active Expired - Lifetime
-
2002
- 2002-08-16 CN CN02130213A patent/CN1440967A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ATE288427T1 (de) | 2005-02-15 |
| JP2001501613A (ja) | 2001-02-06 |
| CN1230953A (zh) | 1999-10-06 |
| AU4502197A (en) | 1998-04-17 |
| EP0935596A1 (en) | 1999-08-18 |
| EP0935596B1 (en) | 2005-02-02 |
| WO1998013360A1 (en) | 1998-04-02 |
| EP0935596A4 (en) | 1999-10-27 |
| CA2266892A1 (en) | 1998-04-02 |
| IL129100A (en) | 2004-03-28 |
| IL129100A0 (en) | 2000-02-17 |
| US6133462A (en) | 2000-10-17 |
| AU736591B2 (en) | 2001-08-02 |
| CA2266892C (en) | 2005-12-06 |
| US5750737A (en) | 1998-05-12 |
| CN1440967A (zh) | 2003-09-10 |
| CN1097586C (zh) | 2003-01-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8332 | No legal effect for de |