FI106959B - Förfarande för framställning av taxanderivat - Google Patents
Förfarande för framställning av taxanderivat Download PDFInfo
- Publication number
- FI106959B FI106959B FI943643A FI943643A FI106959B FI 106959 B FI106959 B FI 106959B FI 943643 A FI943643 A FI 943643A FI 943643 A FI943643 A FI 943643A FI 106959 B FI106959 B FI 106959B
- Authority
- FI
- Finland
- Prior art keywords
- radical
- process according
- general formula
- esterification
- hydroxy function
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 13
- DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class 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 title claims abstract description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- 230000032050 esterification Effects 0.000 claims abstract description 10
- 238000005886 esterification reaction Methods 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical group C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 claims abstract description 5
- 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 3
- 150000005840 aryl radicals Chemical class 0.000 claims abstract description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 3
- -1 tert-butoxycarbonyl radical Chemical class 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical group CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 8
- 125000006239 protecting group Chemical group 0.000 claims description 8
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 6
- RGUKYNXWOWSRET-UHFFFAOYSA-N 4-pyrrolidin-1-ylpyridine Chemical compound C1CCCN1C1=CC=NC=C1 RGUKYNXWOWSRET-UHFFFAOYSA-N 0.000 claims description 5
- 230000003213 activating effect Effects 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 4
- 150000001718 carbodiimides Chemical group 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 150000003927 aminopyridines Chemical group 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- 229930190007 Baccatin Natural products 0.000 claims 1
- OVMSOCFBDVBLFW-VHLOTGQHSA-N 5beta,20-epoxy-1,7beta,13alpha-trihydroxy-9-oxotax-11-ene-2alpha,4alpha,10beta-triyl 4,10-diacetate 2-benzoate Chemical class 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 description 3
- 230000001681 protective effect Effects 0.000 abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 125000004797 2,2,2-trichloroethoxy group Chemical group ClC(CO*)(Cl)Cl 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 229940123237 Taxane Drugs 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000006345 epimerization reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- RBANVFAOLCONSH-JQXSQYPDSA-N (2r,3s)-2-(1-ethoxyethoxy)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoic acid Chemical compound CCOC(C)O[C@@H](C(O)=O)[C@@H](NC(=O)OC(C)(C)C)C1=CC=CC=C1 RBANVFAOLCONSH-JQXSQYPDSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JPORDWFABBLCJT-OLTOQGTGSA-N (2R,3S)-2-amino-2-(1-ethoxyethoxy)-4-[(2-methylpropan-2-yl)oxy]-4-oxo-3-phenylbutanoic acid Chemical compound C1(=CC=CC=C1)[C@@H]([C@](C(=O)O)(OC(C)OCC)N)C(=O)OC(C)(C)C JPORDWFABBLCJT-OLTOQGTGSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 229930014667 baccatin III Natural products 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- BONORRGKLJBGRV-UHFFFAOYSA-N methapyrilene hydrochloride Chemical group Cl.C=1C=CC=NC=1N(CCN(C)C)CC1=CC=CS1 BONORRGKLJBGRV-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- OLRJXMHANKMLTD-UHFFFAOYSA-N silyl Chemical compound [SiH3] OLRJXMHANKMLTD-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Claims (8)
1. Förfarande för framställning av taxanderivat med den allmänna formeln:
5 R-O. 0 OH Rr=H o /—% JL OH : ÖCOCH, 10 - 5 ococ6h5 väri Ar är en arylredikal, R är en väteatom eller en acet-ylradikal och Rx är en bensoyl- eller tert-butoxikarbonyl-radikal genora förestring av ett baccatin III- eller 10-de-15 acetylbaccatin III-derivat med den allmänna formeln: G2-°v ,0 O-Gj >_M,X HO iimi/ OH 5 ÖCOCHj öcoc6h5 väri Gx är en skyddsgrupp för hydroxifunktionen säsom en t. 25 2,2,2-trikloretoxikarbonylradikal eller trialkylsilylra- dikal, väri varje alkyldel innehäller 1-4 kolatomer och G2 är en acetylradikal eller en skyddsgrupp för hydroxifunktionen säsom en 2,2,2-trikloretoxikarbonylradikal med hjälp av en syra med den allmänna formeln:
30 R.-NH A·*- ö-r2 · ,, 106959 väri Ar och är säsom tidigare definierats och R2 är en skyddsgrupp för hydroxifunktionen säsom en metoximetyl-, 1-etoxietyl-, bentsyloximetyl-, (B-trimetylsilyletoxi)met-yl-, tetrahydropyranyl-, 2,2,2-trikloretoximetyl- eller 5 2,2,2-trikloretoxikarbonylradikal, varefter man ersätter skyddsgrupperna G2, G2 och R2 i den erhällna föreningen med väteatomer, kännetecknat av, att förestringen utgörs vid en temperatur mellan -10 och 60 °C (60 °C icke inkluderad). 10 2. Förfarande enligt patentkrav 1, känne tecknat av, att förestringen utförs i ett organiskt lösningsmedel, valt bland etrar, ketoner, estrar, nitri-ler, alifatiska kolväten, klorerade alifatiska kolväten och aromatiska kolväten. 15 3. Förfarande enligt patentkrav 2, känne tecknat av, att lösningsmedlet valts bland estrar och aromatiska kolväten.
4. Förfarande enligt nägot av patentkraven 1, 2 eller 3, kännetecknat av, att omsättningen 20 sker i närvaro av ett kondenseringsmedel och ett aktive-ringsmedel.
5. Förfarande enligt patentkrav 4, kännetecknat av, att kondenseringsmedlet är en karbodi-imid. 25 6. Förfarande enligt patentkrav 4, känne tecknat av, att aktiveringsmedlet är ett aminopy-ridin.
7. Förfarande enligt patentkrav 5, kännetecknat av, att karbodi-imiden är dicyklohexyl- 30 karbodi-imid.
8. Förfarande enligt patentkrav 6, k ä n n e -t e c k n a t av, att aminopyridinet är 4-dimetylamino-pyridin eller 4-pyrrolidinopyridin. • * »
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9201379A FR2687150B1 (fr) | 1992-02-07 | 1992-02-07 | Procede de preparation de derives du taxane. |
| FR9201379 | 1992-02-07 | ||
| FR9300110 | 1993-02-04 | ||
| PCT/FR1993/000110 WO1993016059A1 (fr) | 1992-02-07 | 1993-02-04 | Procede de preparation de derives du taxane |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI943643A0 FI943643A0 (sv) | 1994-08-05 |
| FI943643A7 FI943643A7 (sv) | 1994-08-05 |
| FI106959B true FI106959B (sv) | 2001-05-15 |
Family
ID=9426424
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI943643A FI106959B (sv) | 1992-02-07 | 1994-08-05 | Förfarande för framställning av taxanderivat |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US6596880B1 (sv) |
| EP (1) | EP0625147B1 (sv) |
| JP (1) | JP3295879B2 (sv) |
| KR (1) | KR100254167B1 (sv) |
| AT (1) | ATE141920T1 (sv) |
| AU (1) | AU686095B2 (sv) |
| CA (1) | CA2126462C (sv) |
| CZ (1) | CZ283377B6 (sv) |
| DE (1) | DE69304309T2 (sv) |
| DK (1) | DK0625147T3 (sv) |
| ES (1) | ES2090970T3 (sv) |
| FI (1) | FI106959B (sv) |
| FR (1) | FR2687150B1 (sv) |
| GR (1) | GR3020894T3 (sv) |
| HU (1) | HU212577B (sv) |
| MX (1) | MX9300622A (sv) |
| NO (1) | NO305863B1 (sv) |
| NZ (1) | NZ249162A (sv) |
| PL (1) | PL175106B1 (sv) |
| RU (1) | RU2103266C1 (sv) |
| SK (1) | SK280012B6 (sv) |
| TW (1) | TW234122B (sv) |
| WO (1) | WO1993016059A1 (sv) |
| ZA (1) | ZA93823B (sv) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6794523B2 (en) | 1991-09-23 | 2004-09-21 | Florida State University | Taxanes having t-butoxycarbonyl substituted side-chains and pharmaceutical compositions containing them |
| CA2100808A1 (en) * | 1992-10-01 | 1994-04-02 | Vittorio Farina | Deoxy paclitaxels |
| BR9405687C1 (pt) * | 1993-02-05 | 2001-08-07 | Bryn Mawr College | Processo quìmico utilizável na produção de análogos de taxol e, composto quìmico |
| US5684175A (en) * | 1993-02-05 | 1997-11-04 | Napro Biotherapeutics, Inc. | C-2' hydroxyl-benzyl protected, N-carbamate protected (2R, 3S)- 3-phenylisoserine and production process therefor |
| US5948919A (en) * | 1993-02-05 | 1999-09-07 | Napro Biotherapeutics, Inc. | Paclitaxel synthesis from precursor compounds and methods of producing the same |
| EP0700910A1 (en) * | 1994-09-06 | 1996-03-13 | Shionogi & Co., Ltd. | Process for isolation of taxol from Taxus sumatrana |
| US5580899A (en) * | 1995-01-09 | 1996-12-03 | The Liposome Company, Inc. | Hydrophobic taxane derivatives |
| US5675025A (en) * | 1995-06-07 | 1997-10-07 | Napro Biotherapeutics, Inc. | Paclitaxel synthesis from precursor compounds and methods of producing the same |
| US6107332A (en) | 1995-09-12 | 2000-08-22 | The Liposome Company, Inc. | Hydrolysis-promoting hydrophobic taxane derivatives |
| US6051600A (en) * | 1995-09-12 | 2000-04-18 | Mayhew; Eric | Liposomal hydrolysis-promoting hydrophobic taxane derivatives |
| FR2740451B1 (fr) * | 1995-10-27 | 1998-01-16 | Seripharm | Nouveaux intermediaires pour l'hemisynthese de taxanes, leurs procedes de preparation et leur utilisation dans la synthese generale des taxanes |
| US5688977A (en) * | 1996-02-29 | 1997-11-18 | Napro Biotherapeutics, Inc. | Method for docetaxel synthesis |
| US5750737A (en) * | 1996-09-25 | 1998-05-12 | Sisti; Nicholas J. | Method for paclitaxel synthesis |
| HK1042302B (en) * | 1999-05-17 | 2004-10-08 | Bristol-Myers Squibb Company | Novel reaction conditions for the cleavage of silyl ethers in the preparation of paclitaxel (taxol) and paclitaxel analogues |
| AU776765B2 (en) | 2000-02-02 | 2004-09-23 | Florida State University Research Foundation, Inc. | C7 heterosubstituted acetate taxanes as antitumor agents |
| AU776122B2 (en) | 2000-02-02 | 2004-08-26 | Florida State University Research Foundation, Inc. | C7 carbonate substituted taxanes as antitumor agents |
| IT1319168B1 (it) * | 2000-03-17 | 2003-09-26 | Indena Spa | Derivati di condensazione ad attivita' antitumorale, loro metodo dipreparazione e formulazioni che li contengono. |
| US6452025B1 (en) | 2001-04-25 | 2002-09-17 | Napro Biotherapeutics, Inc. | Three-step conversion of protected taxane ester to paclitaxel |
| WO2005095959A2 (en) * | 2004-03-29 | 2005-10-13 | Howard Murad | Methods for treating dermatological conditions in a patient |
| CN100586940C (zh) * | 2007-01-26 | 2010-02-03 | 上海百灵医药科技有限公司 | 紫杉醇和多烯紫杉醇的半合成方法 |
| KR101014438B1 (ko) * | 2008-09-26 | 2011-02-14 | 동아제약주식회사 | 탁산 유도체의 제조방법 |
| PL388144A1 (pl) | 2009-05-29 | 2010-12-06 | Przedsiębiorstwo Produkcyjno-Wdrożeniowe Ifotam Spółka Z Ograniczoną Odpowiedzialnością | Solwaty (2R,3S)-3-tert-butoksykarbonylamino-2-hydroksy-3-fenylopropionianu 4-acetoksy-2α-benzoiloksy -5β,20-epoksy-1,7β,10β-trihydroksy-9-okso-taks-11-en-13α-ylu, sposób ich otrzymywania i zastosowanie |
| US8829210B2 (en) * | 2011-04-01 | 2014-09-09 | Shilpa Medicare Limited | Process for preparing docetaxel and its hydrate |
| KR101626703B1 (ko) | 2012-04-04 | 2016-06-02 | 할로자임, 아이엔씨 | 항-히알루로난 제제 및 종양-표적 탁산을 이용한 병용 치료 |
| BR112014031421A2 (pt) | 2012-06-15 | 2017-06-27 | Brigham & Womens Hospital Inc | composições para tratamento de câncer e métodos para produção das mesmas |
| AU2015241198A1 (en) | 2014-04-03 | 2016-11-17 | Invictus Oncology Pvt. Ltd. | Supramolecular combinatorial therapeutics |
| US20190351031A1 (en) | 2018-05-16 | 2019-11-21 | Halozyme, Inc. | Methods of selecting subjects for combination cancer therapy with a polymer-conjugated soluble ph20 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR336841A (fr) | 1903-10-29 | 1904-03-18 | James William Mander | Perfectionnements apportés aux instruments employés pour le dessin |
| FR336840A (fr) | 1903-10-29 | 1904-03-18 | Emmanuel Saura | Machine à piston diviseur |
| 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 |
| FR2629818B1 (fr) | 1988-04-06 | 1990-11-16 | Centre Nat Rech Scient | Procede de preparation du taxol |
-
1992
- 1992-02-07 FR FR9201379A patent/FR2687150B1/fr not_active Expired - Fee Related
-
1993
- 1993-02-04 KR KR1019940702713A patent/KR100254167B1/ko not_active Expired - Lifetime
- 1993-02-04 AT AT93904150T patent/ATE141920T1/de active
- 1993-02-04 AU AU35048/93A patent/AU686095B2/en not_active Expired
- 1993-02-04 EP EP93904150A patent/EP0625147B1/fr not_active Expired - Lifetime
- 1993-02-04 NZ NZ249162A patent/NZ249162A/en not_active IP Right Cessation
- 1993-02-04 ES ES93904150T patent/ES2090970T3/es not_active Expired - Lifetime
- 1993-02-04 SK SK930-94A patent/SK280012B6/sk not_active IP Right Cessation
- 1993-02-04 DE DE69304309T patent/DE69304309T2/de not_active Expired - Lifetime
- 1993-02-04 PL PL93304721A patent/PL175106B1/pl unknown
- 1993-02-04 MX MX9300622A patent/MX9300622A/es unknown
- 1993-02-04 CA CA002126462A patent/CA2126462C/fr not_active Expired - Lifetime
- 1993-02-04 DK DK93904150.5T patent/DK0625147T3/da active
- 1993-02-04 US US08/256,736 patent/US6596880B1/en not_active Expired - Lifetime
- 1993-02-04 JP JP51356393A patent/JP3295879B2/ja not_active Expired - Fee Related
- 1993-02-04 TW TW082100755A patent/TW234122B/zh not_active IP Right Cessation
- 1993-02-04 CZ CZ941870A patent/CZ283377B6/cs not_active IP Right Cessation
- 1993-02-04 HU HU9402289A patent/HU212577B/hu unknown
- 1993-02-04 RU RU94040356A patent/RU2103266C1/ru active
- 1993-02-04 WO PCT/FR1993/000110 patent/WO1993016059A1/fr not_active Ceased
- 1993-02-05 ZA ZA93823A patent/ZA93823B/xx unknown
-
1994
- 1994-08-04 NO NO942895A patent/NO305863B1/no not_active IP Right Cessation
- 1994-08-05 FI FI943643A patent/FI106959B/sv not_active IP Right Cessation
-
1996
- 1996-08-29 GR GR960401046T patent/GR3020894T3/el unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI106959B (sv) | Förfarande för framställning av taxanderivat | |
| KR100290663B1 (ko) | 박카틴iii및10-데아세틸박카틴iii의신규한에스테르화방법 | |
| EP0663908B1 (fr) | Procede de preparation de derives du taxane | |
| CZ283362B6 (cs) | Způsob přípravy derivátů taxanu | |
| AU9095098A (en) | Novel taxane derivatives | |
| EP1562927B1 (en) | Thio-analogues of paclitaxel and intermediates thereof | |
| US5686623A (en) | Method for preparing taxane derivatives | |
| IL95436A (en) | Method for the preparation of phenzlisoserine derivatives | |
| KR100545436B1 (ko) | 파크리탁셀과 그 동족체의 반합성에 유용한 중간체와 그제조방법 | |
| US5304670A (en) | Process for the enantioselective preparation of phenylisoserine derivatives | |
| US5049689A (en) | Process for the selective n-acylation of aminohydroxamic acid derivatives and starting materials used therein | |
| KR100290664B1 (ko) | 베타-페닐이소세린유도체의입체선택적제조및탁산유도체의제조시이의사용을위한방법 | |
| RU2104274C1 (ru) | Ангидриды кислот, способ их получения, способы получения таксола или таксотера | |
| US6583292B2 (en) | Method for the esterification of alcohols and compounds useful therefor as potential anticancer agents | |
| SK126496A3 (en) | Process for the preparation of 7-hydroxy taxanes | |
| WO2002012216A1 (en) | An improved process for the preparation of docetaxel | |
| FR2745809A1 (fr) | Procede de preparation d'isoserines utiles dans la synthese de taxoides therapeutiquement actifs |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MA | Patent expired |