FI115970B - Menetelmä 7-trialkyylisilyylibakkatiini III:n valmistamiseksi - Google Patents
Menetelmä 7-trialkyylisilyylibakkatiini III:n valmistamiseksi Download PDFInfo
- Publication number
- FI115970B FI115970B FI964001A FI964001A FI115970B FI 115970 B FI115970 B FI 115970B FI 964001 A FI964001 A FI 964001A FI 964001 A FI964001 A FI 964001A FI 115970 B FI115970 B FI 115970B
- Authority
- FI
- Finland
- Prior art keywords
- iii
- process according
- general formula
- preparation
- carbon atoms
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- YWLXLRUDGLRYDR-ZHPRIASZSA-N 5beta,20-epoxy-1,7beta,10beta,13alpha-tetrahydroxy-9-oxotax-11-ene-2alpha,4alpha-diyl 4-acetate 2-benzoate Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](O)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 YWLXLRUDGLRYDR-ZHPRIASZSA-N 0.000 claims abstract description 20
- -1 alkyl radicals Chemical class 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 3
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims abstract description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- OVMSOCFBDVBLFW-VHLOTGQHSA-N (-)-Baccatin III Natural products 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 claims description 5
- 229930014667 baccatin III Natural products 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 3
- RQMWVVBHJMUJNZ-UHFFFAOYSA-N 4-chloropyridin-2-amine Chemical group NC1=CC(Cl)=CC=N1 RQMWVVBHJMUJNZ-UHFFFAOYSA-N 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 3
- 238000006884 silylation reaction Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000021736 acetylation Effects 0.000 description 2
- 238000006640 acetylation reaction Methods 0.000 description 2
- DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229930190007 Baccatin Natural products 0.000 description 1
- 229930012538 Paclitaxel Natural products 0.000 description 1
- 229940123237 Taxane Drugs 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229960001592 paclitaxel Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical group C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 description 1
- 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 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/188—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epoxy Compounds (AREA)
- Silicon Compounds (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
- Peptides Or Proteins (AREA)
- Liquid Deposition Of Substances Of Which Semiconductor Devices Are Composed (AREA)
- Saccharide Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Magnetic Resonance Imaging Apparatus (AREA)
- Internal Circuitry In Semiconductor Integrated Circuit Devices (AREA)
- Cephalosporin Compounds (AREA)
- Steroid Compounds (AREA)
- Silicon Polymers (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9403979 | 1994-04-05 | ||
| FR9403979A FR2718137B1 (fr) | 1994-04-05 | 1994-04-05 | Procédé de préparation de trialcoylsilyl-7 baccatine III. |
| PCT/FR1995/000419 WO1995026967A1 (fr) | 1994-04-05 | 1995-04-03 | Procede de preparation de trialcoylsilyl-7 baccatine iii |
| FR9500419 | 1995-04-03 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI964001L FI964001L (fi) | 1996-10-04 |
| FI964001A0 FI964001A0 (fi) | 1996-10-04 |
| FI115970B true FI115970B (fi) | 2005-08-31 |
Family
ID=9461745
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI964001A FI115970B (fi) | 1994-04-05 | 1996-10-04 | Menetelmä 7-trialkyylisilyylibakkatiini III:n valmistamiseksi |
Country Status (33)
| Country | Link |
|---|---|
| US (1) | US5670658A (https=) |
| EP (1) | EP0754185B1 (https=) |
| JP (1) | JP3718225B2 (https=) |
| KR (1) | KR100399246B1 (https=) |
| CN (1) | CN1058497C (https=) |
| AT (1) | ATE160351T1 (https=) |
| AU (1) | AU683560B2 (https=) |
| BG (1) | BG62735B1 (https=) |
| BR (1) | BR9507444A (https=) |
| CA (1) | CA2186916C (https=) |
| CZ (1) | CZ288397B6 (https=) |
| DE (1) | DE69501080T2 (https=) |
| DK (1) | DK0754185T3 (https=) |
| EE (1) | EE03240B1 (https=) |
| ES (1) | ES2109103T3 (https=) |
| FI (1) | FI115970B (https=) |
| FR (1) | FR2718137B1 (https=) |
| GE (1) | GEP19991537B (https=) |
| GR (1) | GR3025448T3 (https=) |
| HU (1) | HU214158B (https=) |
| LT (1) | LT4185B (https=) |
| LV (1) | LV11691B (https=) |
| MX (1) | MX9604466A (https=) |
| NO (1) | NO305839B1 (https=) |
| NZ (1) | NZ284490A (https=) |
| PL (1) | PL316588A1 (https=) |
| RO (1) | RO115631B1 (https=) |
| RU (1) | RU2127729C1 (https=) |
| SK (1) | SK280448B6 (https=) |
| TW (1) | TW284765B (https=) |
| UA (1) | UA44730C2 (https=) |
| WO (1) | WO1995026967A1 (https=) |
| ZA (1) | ZA952733B (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5973160A (en) * | 1992-12-23 | 1999-10-26 | Poss; Michael A. | Methods for the preparation of novel sidechain-bearing taxanes |
| US7288665B1 (en) * | 1997-08-18 | 2007-10-30 | Florida State University | Process for selective derivatization of taxanes |
| CA2302699A1 (en) | 1997-08-21 | 1999-02-25 | Florida State University | Method for the synthesis of taxanes |
| HUP0302599A3 (en) | 2000-09-22 | 2005-05-30 | Bristol Myers Squibb Co | Method for reducing toxicity of combined chemotherapic compositions |
| ITMI20012185A1 (it) * | 2001-10-19 | 2003-04-19 | Indena Spa | Procedimento per la preparazione della 14beta-idrossi-baccatina iii-1,14-carbonato |
| ITMI20012186A1 (it) * | 2001-10-19 | 2003-04-19 | Indena Spa | Procedimento per la preparazione della 14-beta-idrossi-baccatina iii-1,14-carbonato |
| JP2006513152A (ja) * | 2002-10-09 | 2006-04-20 | ファイトジェン ライフ サイエンシズ インコーポレイテッド | 新規タキサンならびにその使用および調製に関する方法 |
| US7202370B2 (en) * | 2003-10-27 | 2007-04-10 | Conor Medsystems, Inc. | Semi-synthesis of taxane intermediates from 9-dihydro-13-acetylbaccatin III |
| BRPI0511109A (pt) * | 2004-05-14 | 2007-11-27 | Immunogen Inc | método fácil para sintetizar compostos de baccatin iii |
| CZ298333B6 (cs) * | 2005-09-26 | 2007-08-29 | Zentiva, A. S | Zpusob prípravy 7-trialkylsilylbaccatinu III |
| KR101671537B1 (ko) | 2008-08-11 | 2016-11-01 | 넥타르 테라퓨틱스 | 다분지형 중합체 알카노에이트 컨쥬게이트 |
| WO2012088422A1 (en) | 2010-12-22 | 2012-06-28 | Nektar Therapeutics | Multi-arm polymeric prodrug conjugates of taxane-based compounds |
| US10894087B2 (en) | 2010-12-22 | 2021-01-19 | Nektar Therapeutics | Multi-arm polymeric prodrug conjugates of cabazitaxel-based compounds |
| WO2012088391A1 (en) | 2010-12-22 | 2012-06-28 | Nektar Therapeutics | Non-ring hydroxy substituted taxanes and methods for synthesizing the same |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4823167A (en) * | 1986-12-16 | 1989-04-18 | Baxter International Inc. | Catheter calibration device |
| FR2629818B1 (fr) * | 1988-04-06 | 1990-11-16 | Centre Nat Rech Scient | Procede de preparation du taxol |
| MX9102128A (es) | 1990-11-23 | 1992-07-08 | Rhone Poulenc Rorer Sa | Derivados de taxano,procedimiento para su preparacion y composicion farmaceutica que los contiene |
| US5229526A (en) * | 1991-09-23 | 1993-07-20 | Florida State University | Metal alkoxides |
| US5597931A (en) * | 1992-03-30 | 1997-01-28 | Sloan-Kettering Institute For Cancer Research | Total synthesis of taxol and analogues thereof |
| US5475011A (en) * | 1993-03-26 | 1995-12-12 | The Research Foundation Of State University Of New York | Anti-tumor compounds, pharmaceutical compositions, methods for preparation thereof and for treatment |
| US5405972A (en) * | 1993-07-20 | 1995-04-11 | Florida State University | Synthetic process for the preparation of taxol and other tricyclic and tetracyclic taxanes |
| US5449790A (en) * | 1994-04-06 | 1995-09-12 | Hauser Chemical Research, Inc. | Preparation of 10-deacetylbaccatin III and 7-protected-10-deacetylbaccatin III derivatives from 10-deacetyl taxol A, 10-deacetyl taxol B, and 10-deacetyl taxol C |
-
1994
- 1994-04-05 FR FR9403979A patent/FR2718137B1/fr not_active Expired - Fee Related
-
1995
- 1995-03-22 TW TW084102793A patent/TW284765B/zh not_active IP Right Cessation
- 1995-04-03 JP JP52546695A patent/JP3718225B2/ja not_active Expired - Lifetime
- 1995-04-03 AT AT95916696T patent/ATE160351T1/de active
- 1995-04-03 RU RU96120192/04A patent/RU2127729C1/ru active
- 1995-04-03 US US08/722,103 patent/US5670658A/en not_active Expired - Lifetime
- 1995-04-03 EE EE9600143A patent/EE03240B1/xx unknown
- 1995-04-03 WO PCT/FR1995/000419 patent/WO1995026967A1/fr not_active Ceased
- 1995-04-03 BR BR9507444A patent/BR9507444A/pt not_active IP Right Cessation
- 1995-04-03 KR KR1019960705642A patent/KR100399246B1/ko not_active Expired - Fee Related
- 1995-04-03 PL PL95316588A patent/PL316588A1/xx unknown
- 1995-04-03 NZ NZ284490A patent/NZ284490A/en not_active IP Right Cessation
- 1995-04-03 RO RO96-01921A patent/RO115631B1/ro unknown
- 1995-04-03 HU HU9602735A patent/HU214158B/hu unknown
- 1995-04-03 DE DE69501080T patent/DE69501080T2/de not_active Expired - Lifetime
- 1995-04-03 UA UA96093735A patent/UA44730C2/uk unknown
- 1995-04-03 AU AU23096/95A patent/AU683560B2/en not_active Expired
- 1995-04-03 SK SK1265-96A patent/SK280448B6/sk not_active IP Right Cessation
- 1995-04-03 MX MX9604466A patent/MX9604466A/es unknown
- 1995-04-03 ES ES95916696T patent/ES2109103T3/es not_active Expired - Lifetime
- 1995-04-03 GE GEAP19953433A patent/GEP19991537B/en unknown
- 1995-04-03 CZ CZ19962900A patent/CZ288397B6/cs not_active IP Right Cessation
- 1995-04-03 EP EP95916696A patent/EP0754185B1/fr not_active Expired - Lifetime
- 1995-04-03 CA CA002186916A patent/CA2186916C/fr not_active Expired - Lifetime
- 1995-04-03 ZA ZA952733A patent/ZA952733B/xx unknown
- 1995-04-03 DK DK95916696.8T patent/DK0754185T3/da active
- 1995-04-03 CN CN95192429A patent/CN1058497C/zh not_active Expired - Lifetime
-
1996
- 1996-09-24 LT LT96-137A patent/LT4185B/lt not_active IP Right Cessation
- 1996-09-27 NO NO964103A patent/NO305839B1/no not_active IP Right Cessation
- 1996-10-04 BG BG100886A patent/BG62735B1/bg unknown
- 1996-10-04 FI FI964001A patent/FI115970B/fi not_active IP Right Cessation
- 1996-10-07 LV LVP-96-392A patent/LV11691B/lv unknown
-
1997
- 1997-11-20 GR GR970401504T patent/GR3025448T3/el unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PC | Transfer of assignment of patent |
Owner name: AVENTIS PHARMA S.A. |
|
| FG | Patent granted |
Ref document number: 115970 Country of ref document: FI |
|
| MA | Patent expired |