LT3465B - Process for preparing deacylated 10-baccatine iii - Google Patents
Process for preparing deacylated 10-baccatine iii Download PDFInfo
- Publication number
- LT3465B LT3465B LTIP1398A LTIP1398A LT3465B LT 3465 B LT3465 B LT 3465B LT IP1398 A LTIP1398 A LT IP1398A LT IP1398 A LTIP1398 A LT IP1398A LT 3465 B LT3465 B LT 3465B
- Authority
- LT
- Lithuania
- Prior art keywords
- deacetyl
- process according
- baccatin iii
- organic solvent
- aqueous solution
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 52
- 241001116500 Taxus Species 0.000 claims abstract description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000003960 organic solvent Substances 0.000 claims abstract description 29
- 239000007864 aqueous solution Substances 0.000 claims abstract description 28
- 241001116498 Taxus baccata Species 0.000 claims abstract description 9
- 238000010956 selective crystallization Methods 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 238000003795 desorption Methods 0.000 claims abstract description 4
- 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 claims description 160
- 229930014667 baccatin III Natural products 0.000 claims description 80
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 30
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 27
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 18
- 241000196324 Embryophyta Species 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 229930012538 Paclitaxel Natural products 0.000 claims description 15
- 229960001592 paclitaxel Drugs 0.000 claims description 15
- 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 claims description 15
- 239000000284 extract Substances 0.000 claims description 13
- 238000001914 filtration Methods 0.000 claims description 10
- -1 i.e. Chemical compound 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
- 235000009065 Taxus cuspidata Nutrition 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 8
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical group COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 7
- 239000011347 resin Substances 0.000 claims description 7
- 229920005989 resin Polymers 0.000 claims description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)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 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims description 6
- 238000010908 decantation Methods 0.000 claims description 6
- 229940063683 taxotere Drugs 0.000 claims description 6
- 235000013311 vegetables Nutrition 0.000 claims description 6
- 238000007710 freezing Methods 0.000 claims description 5
- 230000008014 freezing Effects 0.000 claims description 5
- NUMQCACRALPSHD-UHFFFAOYSA-N tert-butyl ethyl ether Chemical compound CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 claims description 5
- 238000010257 thawing Methods 0.000 claims description 5
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- 241000202349 Taxus brevifolia Species 0.000 claims description 4
- 238000005119 centrifugation Methods 0.000 claims description 4
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 4
- 229940011051 isopropyl acetate Drugs 0.000 claims description 4
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 claims description 4
- 239000002594 sorbent Substances 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 3
- 241000015728 Taxus canadensis Species 0.000 claims description 3
- 241000013869 Taxus floridana Species 0.000 claims description 3
- 241001674343 Taxus x media Species 0.000 claims description 3
- 239000008346 aqueous phase Substances 0.000 claims description 3
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 241000894007 species Species 0.000 claims description 3
- RQUBQBFVDOLUKC-UHFFFAOYSA-N 1-ethoxy-2-methylpropane Chemical compound CCOCC(C)C RQUBQBFVDOLUKC-UHFFFAOYSA-N 0.000 claims description 2
- BPIUIOXAFBGMNB-UHFFFAOYSA-N 1-hexoxyhexane Chemical compound CCCCCCOCCCCCC BPIUIOXAFBGMNB-UHFFFAOYSA-N 0.000 claims description 2
- CXBDYQVECUFKRK-UHFFFAOYSA-N 1-methoxybutane Chemical compound CCCCOC CXBDYQVECUFKRK-UHFFFAOYSA-N 0.000 claims description 2
- GPDFVOVLOXMSBT-UHFFFAOYSA-N 1-propan-2-yloxybutane Chemical compound CCCCOC(C)C GPDFVOVLOXMSBT-UHFFFAOYSA-N 0.000 claims description 2
- HFZLSTDPRQSZCQ-UHFFFAOYSA-N 1-pyrrolidin-3-ylpyrrolidine Chemical compound C1CCCN1C1CNCC1 HFZLSTDPRQSZCQ-UHFFFAOYSA-N 0.000 claims description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 2
- 241001330449 Taxus wallichiana Species 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 229940072049 amyl acetate Drugs 0.000 claims description 2
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 claims description 2
- 239000006286 aqueous extract Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000010981 drying operation Methods 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 229940093499 ethyl acetate Drugs 0.000 claims description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 claims description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 2
- 229940090181 propyl acetate Drugs 0.000 claims description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims 2
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 claims 2
- AOPDRZXCEAKHHW-UHFFFAOYSA-N 1-pentoxypentane Chemical compound CCCCCOCCCCC AOPDRZXCEAKHHW-UHFFFAOYSA-N 0.000 claims 1
- FITVQUMLGWRKKG-UHFFFAOYSA-N 2-methyl-2-propoxypropane Chemical compound CCCOC(C)(C)C FITVQUMLGWRKKG-UHFFFAOYSA-N 0.000 claims 1
- DXBOTVWRXLQVMG-UHFFFAOYSA-N methyl 3,3-dimethylbutanoate Chemical compound COC(=O)CC(C)(C)C DXBOTVWRXLQVMG-UHFFFAOYSA-N 0.000 claims 1
- 238000002604 ultrasonography Methods 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 8
- 238000000605 extraction Methods 0.000 abstract description 6
- 238000001179 sorption measurement Methods 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 2
- 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 abstract 3
- 239000000706 filtrate Substances 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 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 description 6
- 239000007787 solid Substances 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229940123237 Taxane Drugs 0.000 description 2
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000011002 quantification Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QOOQLKSEGVNYLA-UHFFFAOYSA-N 1-$l^{1}-oxidanylbutane Chemical group CCCC[O] QOOQLKSEGVNYLA-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- DBUJFULDVAZULB-UHFFFAOYSA-N 1-methoxypentane Chemical compound CCCCCOC DBUJFULDVAZULB-UHFFFAOYSA-N 0.000 description 1
- YGZQJYIITOMTMD-UHFFFAOYSA-N 1-propoxybutane Chemical compound CCCCOCCC YGZQJYIITOMTMD-UHFFFAOYSA-N 0.000 description 1
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 1
- 240000000073 Achillea millefolium Species 0.000 description 1
- 235000007754 Achillea millefolium Nutrition 0.000 description 1
- 229930190007 Baccatin Natural products 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000719 anti-leukaemic effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- BAUZLFKYYIVGPM-UHFFFAOYSA-N cyclononanone Chemical compound O=C1CCCCCCCC1 BAUZLFKYYIVGPM-UHFFFAOYSA-N 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000002611 ovarian Effects 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000009210 therapy by ultrasound Methods 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epoxy Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Compounds Of Unknown Constitution (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Extraction Or Liquid Replacement (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9211745A FR2696462B1 (fr) | 1992-10-05 | 1992-10-05 | Procédé d'obtention de la désacétyl-10 baccatine III. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LTIP1398A LTIP1398A (en) | 1994-11-25 |
| LT3465B true LT3465B (en) | 1995-10-25 |
Family
ID=9434123
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LTIP1398A LT3465B (en) | 1992-10-05 | 1993-10-04 | Process for preparing deacylated 10-baccatine iii |
Country Status (30)
| Country | Link |
|---|---|
| US (2) | US5393896A (lv) |
| EP (1) | EP0663909B1 (lv) |
| JP (1) | JP3299753B2 (lv) |
| KR (1) | KR100301238B1 (lv) |
| CN (1) | CN1041310C (lv) |
| AT (1) | ATE147381T1 (lv) |
| AU (1) | AU680440B2 (lv) |
| CA (2) | CA2146248C (lv) |
| CZ (2) | CZ286452B6 (lv) |
| DE (1) | DE69307333T2 (lv) |
| DK (1) | DK0663909T3 (lv) |
| EE (1) | EE03124B1 (lv) |
| ES (1) | ES2095672T3 (lv) |
| FI (1) | FI109797B (lv) |
| FR (1) | FR2696462B1 (lv) |
| GE (1) | GEP19981433B (lv) |
| GR (1) | GR3022229T3 (lv) |
| HU (1) | HU225969B1 (lv) |
| LT (1) | LT3465B (lv) |
| LV (1) | LV10620B (lv) |
| MX (1) | MX9305770A (lv) |
| NO (1) | NO310414B1 (lv) |
| NZ (1) | NZ256449A (lv) |
| PL (1) | PL173993B1 (lv) |
| RU (1) | RU2108330C1 (lv) |
| SK (1) | SK280335B6 (lv) |
| TW (1) | TW404944B (lv) |
| UA (1) | UA40601C2 (lv) |
| WO (1) | WO1994007881A1 (lv) |
| ZA (1) | ZA937312B (lv) |
Families Citing this family (80)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69435342D1 (de) | 1993-07-19 | 2011-05-05 | Angiotech Pharm Inc | Anti-Angiogene Mittel und Verfahren zu deren Verwendung |
| FR2714053B1 (fr) * | 1993-12-22 | 1996-03-08 | Pf Medicament | Procédé d'extraction et d'isolement de la 10-désacétylbaccatine III. |
| CN1112433A (zh) * | 1994-05-24 | 1995-11-29 | 郭明 | 红豆杉属植物提取物及其应用 |
| CA2178541C (en) | 1995-06-07 | 2009-11-24 | Neal E. Fearnot | Implantable medical device |
| FR2736355B1 (fr) * | 1995-07-07 | 1997-11-07 | Pf Medicament | Procede d'extraction et d'isolement de la 10-desacetylbaccatine iii |
| US5965752A (en) * | 1996-08-23 | 1999-10-12 | Institut National De La Recherche Scientifique | Preparative scale isolation and purification of taxanes |
| AU739303B2 (en) | 1997-08-21 | 2001-10-11 | Florida State University | Method for the synthesis of taxanes |
| US6066748A (en) * | 1997-12-17 | 2000-05-23 | Han; Man Woo | Process of extracting TAXOL® from taxus cuspidata |
| EP1068192B1 (en) | 1998-01-14 | 2002-06-12 | Bristol-Myers Squibb Company | Novel crystalline complexes of baccatin iii with imidazole, 2-methylimidazole or isopropanol |
| WO2002085337A1 (en) | 2001-04-20 | 2002-10-31 | The University Of British Columbia | Micellar drug delivery systems for hydrophobic drugs |
| US6136989A (en) * | 1998-12-30 | 2000-10-24 | Phytogen Life Sciences, Incorporated | Method for high yield and large scale extraction of paclitaxel from paclitaxel-containing material |
| US5969165A (en) * | 1999-01-07 | 1999-10-19 | 508037 (Nb) Inc. | Isolation and purification of paclitaxel and other related taxanes by industrial preparative low pressure chromatography on a polymeric resin column |
| US6281368B1 (en) | 2000-03-16 | 2001-08-28 | Napro Biotherapeutics, Inc. | Simple and efficient hydrazinolysis of C-10 and C-13 ester functionalities of taxanes to obtain 10-DAB III |
| US6495705B2 (en) | 2000-03-16 | 2002-12-17 | Napro Biotherapeutics, Inc. | Efficient process for the production of 10-DAB III by selective hydrazinolysis of various taxanes |
| CA2307393A1 (en) | 2000-05-01 | 2001-11-01 | The University Of British Columbia | Ginsenoside chemotherapy |
| US20030157170A1 (en) * | 2001-03-13 | 2003-08-21 | Richard Liggins | Micellar drug delivery vehicles and precursors thereto and uses thereof |
| CA2440935A1 (en) * | 2001-03-13 | 2002-09-19 | Richard Liggins | Micellar drug delivery vehicles and precursors thereto and uses thereof |
| US7351542B2 (en) | 2002-05-20 | 2008-04-01 | The Regents Of The University Of California | Methods of modulating tubulin deacetylase activity |
| JP2006516548A (ja) | 2002-12-30 | 2006-07-06 | アンジオテック インターナショナル アクツィエン ゲゼルシャフト | 迅速ゲル化ポリマー組成物からの薬物送達法 |
| EP1594668A4 (en) * | 2002-12-31 | 2006-06-07 | Natural Pharmaceuticals Inc | PELLETIZATION OF EIBENBIOMASSE FOR THE EXTRACTION OF TAXANES AND OTHER NATURAL PRODUCTS |
| US20070172446A1 (en) | 2003-05-16 | 2007-07-26 | Intermune, Inc. | Synthetic chemokine receptor ligands and methods of use thereof |
| CA2542532C (en) * | 2003-10-17 | 2012-08-14 | Tyco Healthcare Group, Lp | Surgical stapling device with independent tip rotation |
| US20060127510A1 (en) * | 2003-12-30 | 2006-06-15 | Natural Pharmaceuticals, Inc. | Harvesting and pelletizing yew biomass for extraction of taxanes and other natural products |
| US7846940B2 (en) | 2004-03-31 | 2010-12-07 | Cordis Corporation | Solution formulations of sirolimus and its analogs for CAD treatment |
| US8003122B2 (en) | 2004-03-31 | 2011-08-23 | Cordis Corporation | Device for local and/or regional delivery employing liquid formulations of therapeutic agents |
| US7989490B2 (en) | 2004-06-02 | 2011-08-02 | Cordis Corporation | Injectable formulations of taxanes for cad treatment |
| US20050250954A1 (en) * | 2004-05-04 | 2005-11-10 | Phytogen Life Sciences Inc. | Semi-synthesis and isolation of taxane intermediates from a mixture of taxanes |
| US20050240036A1 (en) * | 2004-04-23 | 2005-10-27 | Phytogen Life Sciences Inc. | Semi-synthesis of taxane intermediates from a mixture of taxanes |
| US20050272807A1 (en) * | 2004-06-04 | 2005-12-08 | Phytogen Life Sciences Inc. | Semi-synthesis of taxane intermediates and their conversion to paclitaxel and docetaxel |
| PL1778660T3 (pl) * | 2004-07-02 | 2009-07-31 | Ivax Pharmaceuticals Sro | Sposób rozdzielania paklitakselu i cefalomanniny |
| US7597884B2 (en) | 2004-08-09 | 2009-10-06 | Alios Biopharma, Inc. | Hyperglycosylated polypeptide variants and methods of use |
| WO2006089209A2 (en) | 2005-02-17 | 2006-08-24 | The Board Of Trustees Of The Leland Stanford Junior University | Txr1 and enhanced taxane sensitivity based on the modulation of a pathway mediated thereby |
| WO2007045093A1 (en) * | 2005-10-21 | 2007-04-26 | Her Majesty The Queen In Right Of Canada As Represented By The Minister Of Natural Resources Canada, Canadian Forest Service | Preparation of taxanes |
| RU2448697C2 (ru) | 2006-03-22 | 2012-04-27 | Медигене Аг | Лечение рака молочной железы, негативного по трем рецепторам |
| WO2008005284A2 (en) | 2006-06-30 | 2008-01-10 | Cook Incorporated | Methods of manufacturing and modifying taxane coatings for implantable medical devices |
| CN100404520C (zh) * | 2006-08-15 | 2008-07-23 | 北京诺瑞医药技术有限公司 | 从欧洲红豆杉枝叶中提取分离10－去乙酰基巴卡汀ⅲ的方法 |
| CN101230053B (zh) * | 2007-12-04 | 2010-06-02 | 北京诺瑞医药技术有限公司 | 从红豆杉枝叶中超声提取分离10-去乙酰基巴卡汀ⅲ的方法 |
| US8420110B2 (en) | 2008-03-31 | 2013-04-16 | Cordis Corporation | Drug coated expandable devices |
| US8409601B2 (en) | 2008-03-31 | 2013-04-02 | Cordis Corporation | Rapamycin coated expandable devices |
| US8273404B2 (en) | 2008-05-19 | 2012-09-25 | Cordis Corporation | Extraction of solvents from drug containing polymer reservoirs |
| WO2009143454A2 (en) | 2008-05-22 | 2009-11-26 | Kereos, Inc. | Combination antitumor therapy |
| EP2310507A4 (en) | 2008-07-08 | 2013-03-20 | David Gladstone Inst | METHODS AND COMPOSITIONS FOR MODULATING ANGIOGENESIS |
| US8642063B2 (en) | 2008-08-22 | 2014-02-04 | Cook Medical Technologies Llc | Implantable medical device coatings with biodegradable elastomer and releasable taxane agent |
| US20120303115A1 (en) | 2011-05-25 | 2012-11-29 | Dadino Ronald C | Expandable devices coated with a rapamycin composition |
| US20120302954A1 (en) | 2011-05-25 | 2012-11-29 | Zhao Jonathon Z | Expandable devices coated with a paclitaxel composition |
| WO2013069027A1 (en) | 2011-09-26 | 2013-05-16 | Fresenius Kabi Oncology Ltd. | Processes for the preparation of cabazitaxel involving c(7) -oh and c(13) -oh silylation or just c(7) -oh silylation |
| US9956385B2 (en) | 2012-06-28 | 2018-05-01 | The Spectranetics Corporation | Post-processing of a medical device to control morphology and mechanical properties |
| EP3539563A1 (en) | 2012-07-19 | 2019-09-18 | Redwood Bioscience, Inc. | Antibody specific for cd22 and methods of use thereof |
| AU2013341711A1 (en) | 2012-11-12 | 2015-05-21 | Redwood Bioscience, Inc. | Compounds and methods for producing a conjugate |
| ES2758227T3 (es) | 2013-02-15 | 2020-05-04 | Univ California | Receptor de antígeno quimérico y métodos de uso del mismo |
| JP6410790B2 (ja) | 2013-03-14 | 2018-10-24 | ザ ボード オブ トラスティーズ オブ ザ レランド スタンフォード ジュニア ユニバーシティー | ミトコンドリアアルデヒドデヒドロゲナーゼ−２調節因子およびその使用方法 |
| CN103508984B (zh) * | 2013-10-22 | 2017-03-08 | 北京诺瑞医药技术有限公司 | 连续浸漉吸附富集法从红豆杉中提取10-dab的方法 |
| CA2927806C (en) | 2013-11-27 | 2023-01-10 | Redwood Bioscience, Inc. | Hydrazinyl-pyrrolo compounds and methods for producing a conjugate |
| US9879036B2 (en) | 2014-02-19 | 2018-01-30 | Aviv Therapeutics, Inc. | Mitochondrial aldehyde dehydrogenase-2 binding compounds and methods of use thereof |
| CN108135917B (zh) | 2015-09-25 | 2021-07-09 | Zy医疗 | 基于包含多糖-维生素缀合物的颗粒的药物制剂 |
| EP3373977A4 (en) | 2015-11-12 | 2019-07-17 | The Board of Trustees of the Leland Stanford Junior University | CELLULAR PENETRATION-RICH GUANIDINIC OLIGOPHOSPHOTRIESTERS FOR THE DELIVERY OF MEDICATION AND PROBE |
| HUP1500603A2 (en) * | 2015-12-11 | 2017-06-28 | Rotachrom Tech Kft | Process for the separation of 10-deacetyl baccatin iii |
| TWI760319B (zh) | 2015-12-30 | 2022-04-11 | 杏國新藥股份有限公司 | 乳癌治療 |
| WO2017189432A1 (en) | 2016-04-26 | 2017-11-02 | R.P. Scherer Technologies, Llc | Antibody conjugates and methods of making and using the same |
| MX2018014916A (es) | 2016-06-01 | 2019-07-18 | Servier Ip Uk Ltd | Formulaciones de oxido de polialquileno-asparaginasa y metodos de preparacion y uso del mismo. |
| CN106397371A (zh) * | 2016-08-31 | 2017-02-15 | 重庆市碚圣医药科技股份有限公司 | 一种用曼地亚红豆杉高产10‑dabⅲ的方法 |
| WO2018127082A1 (en) | 2017-01-05 | 2018-07-12 | Syncore Biotechnology Co., Ltd. | Treatment of pancreatic cancer |
| BR112019014615A2 (pt) | 2017-01-18 | 2020-06-02 | F1 Oncology, Inc. | Receptores de antígeno quimérico contra axl ou ror2 e métodos de uso dos mesmos |
| EP3388082A1 (en) | 2017-04-13 | 2018-10-17 | Galera Labs, LLC | Combination cancer immunotherapy with pentaaza macrocyclic ring complex |
| EA202091832A1 (ru) | 2018-01-31 | 2021-01-11 | ГАЛЕРА ЛЭБЗ, ЭлЭлСи | Комбинированная терапия злокачественных новообразований макроциклическим кольцевым комплексом пентаазы и противоопухолевым агентом на основе платины |
| US11660266B2 (en) | 2018-04-11 | 2023-05-30 | Ohio State Innovation Foundation | Methods and compositions for sustained release microparticles for ocular drug delivery |
| MX2021000644A (es) | 2018-07-18 | 2021-08-19 | Manzanita Pharmaceuticals Inc | Conjugados para suministrar un agente contra el cancer a las celulas nerviosas, metodos de uso y metodos para la elaboracion de los mismos. |
| WO2020148612A1 (en) | 2019-01-14 | 2020-07-23 | Ignite Immunotherapy, Inc. | Recombinant vaccinia virus and methods of use thereof |
| US11685904B2 (en) | 2019-02-14 | 2023-06-27 | Ignite Immunotherapy, Inc. | Recombinant vaccinia virus and methods of use thereof |
| EP3946626A1 (en) | 2019-04-02 | 2022-02-09 | Kenjockety Biotechnology, Inc. | Efflux pump-cancer antigen multi-specific antibodies and compositions, reagents, kits and methods related thereto |
| WO2021116943A1 (en) | 2019-12-12 | 2021-06-17 | Ignite Immunotherapy, Inc. | Variant oncolytic vaccinia virus and methods of use thereof |
| MX2022009355A (es) | 2020-01-29 | 2022-09-02 | Kenjockety Biotechnology Inc | Anticuerpo anti-mdr1 y uso del mismo. |
| EP4161564A1 (en) | 2020-06-04 | 2023-04-12 | Kenjockety Biotechnology, Inc. | Abcg2 efflux pump-cancer antigen multi-specific antibodies and compositions, reagents, kits and methods related thereto |
| US20230212305A1 (en) | 2020-06-04 | 2023-07-06 | Kenjockety Biotechnology, Inc. | Anti-abcg2 antibodies and uses thereof |
| EP4182335A2 (en) | 2020-07-14 | 2023-05-24 | Pfizer Inc. | Recombinant vaccinia virus |
| CA3193588A1 (en) | 2020-09-02 | 2022-03-10 | Kenjockety Biotechnology, Inc. | Anti-abcc1 antibodies and uses thereof |
| CA3203652A1 (en) | 2020-11-13 | 2022-05-19 | William Robert ARATHOON | Anti-mrp4 (encoded by abcc4 gene) antibodies and uses thereof |
| CN112694458A (zh) * | 2020-12-29 | 2021-04-23 | 重庆臻源红豆杉发展有限公司 | 一种10-去乙酰基巴卡亭ⅲ提取纯化方法 |
| AU2022413942A1 (en) | 2021-12-13 | 2024-05-30 | William Robert Arathoon Living Trust Dated August 29, 2016 | Anti-abcb1 antibodies |
| WO2023159220A1 (en) | 2022-02-18 | 2023-08-24 | Kenjockety Biotechnology, Inc. | Anti-cd47 antibodies |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4814470A (en) | 1986-07-17 | 1989-03-21 | Rhone-Poulenc Sante | Taxol derivatives, their preparation and pharmaceutical compositions containing them |
| US4857653A (en) | 1986-07-17 | 1989-08-15 | Rhone-Poulenc Sante | Process for the preparation of taxol and 10-deacetyltaxol |
| US4924012A (en) | 1988-04-06 | 1990-05-08 | Rhone-Poulenc Sante | Process for preparing derivatives of baccatine III and of 10-deacetyl baccatine III |
| EP0400971A2 (en) | 1989-05-31 | 1990-12-05 | Florida State University | Method for preparation of taxol |
| EP0428376A1 (en) | 1989-11-14 | 1991-05-22 | Florida State University | Method for preparation of taxol using an oxazinone |
| WO1992007842A1 (en) | 1990-11-02 | 1992-05-14 | University Of Florida | Method for the isolation and purification of taxane derivatives |
| WO1992009589A1 (fr) | 1990-11-23 | 1992-06-11 | Rhone-Poulenc Rorer S.A. | Procede de preparation de derives du taxane, nouveaux derives obtenus et compositions pharmaceutiques qui les contiennent |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2629818B1 (fr) * | 1988-04-06 | 1990-11-16 | Centre Nat Rech Scient | Procede de preparation du taxol |
| US5019504A (en) * | 1989-03-23 | 1991-05-28 | The United States Of America As Represented By The Secretary Of Agriculture | Production of taxol or taxol-like compounds in cell culture |
| US5279953A (en) * | 1992-06-24 | 1994-01-18 | Esca Genetics Corporation | In vivo production of taxanes |
| FR2696463B1 (fr) * | 1992-10-05 | 1994-11-25 | Rhone Poulenc Rorer Sa | Procédé d'obtention de la désacétyl-10 baccatine III. |
| FR2703049B1 (fr) * | 1993-03-22 | 1995-04-21 | Rhone Poulenc Rorer Sa | Procédé de purification des taxoïdes. |
-
1992
- 1992-10-05 FR FR9211745A patent/FR2696462B1/fr not_active Expired - Lifetime
-
1993
- 1993-01-27 US US08/010,084 patent/US5393896A/en not_active Expired - Lifetime
- 1993-04-21 CN CN93104617A patent/CN1041310C/zh not_active Expired - Lifetime
- 1993-09-21 MX MX9305770A patent/MX9305770A/es unknown
- 1993-10-01 ZA ZA937312A patent/ZA937312B/xx unknown
- 1993-10-02 TW TW082108097A patent/TW404944B/zh not_active IP Right Cessation
- 1993-10-04 DK DK93921986.1T patent/DK0663909T3/da active
- 1993-10-04 CA CA002146248A patent/CA2146248C/fr not_active Expired - Lifetime
- 1993-10-04 DE DE69307333T patent/DE69307333T2/de not_active Expired - Lifetime
- 1993-10-04 WO PCT/FR1993/000971 patent/WO1994007881A1/fr active IP Right Grant
- 1993-10-04 RU RU95110662/04A patent/RU2108330C1/ru active
- 1993-10-04 SK SK431-95A patent/SK280335B6/sk not_active IP Right Cessation
- 1993-10-04 HU HU9500969A patent/HU225969B1/hu unknown
- 1993-10-04 LV LVP-93-1119A patent/LV10620B/xx unknown
- 1993-10-04 JP JP50879194A patent/JP3299753B2/ja not_active Expired - Lifetime
- 1993-10-04 ES ES93921986T patent/ES2095672T3/es not_active Expired - Lifetime
- 1993-10-04 CA CA002470124A patent/CA2470124C/fr not_active Expired - Lifetime
- 1993-10-04 NZ NZ256449A patent/NZ256449A/en not_active IP Right Cessation
- 1993-10-04 PL PL93308243A patent/PL173993B1/pl unknown
- 1993-10-04 LT LTIP1398A patent/LT3465B/lt not_active IP Right Cessation
- 1993-10-04 UA UA95038243A patent/UA40601C2/uk unknown
- 1993-10-04 AU AU51154/93A patent/AU680440B2/en not_active Expired
- 1993-10-04 GE GEAP19932496A patent/GEP19981433B/en unknown
- 1993-10-04 EP EP93921986A patent/EP0663909B1/fr not_active Expired - Lifetime
- 1993-10-04 CZ CZ1995844A patent/CZ286452B6/cs not_active IP Right Cessation
- 1993-10-04 KR KR1019950701305A patent/KR100301238B1/ko not_active IP Right Cessation
- 1993-10-04 AT AT93921986T patent/ATE147381T1/de active
-
1994
- 1994-11-18 EE EE9400336A patent/EE03124B1/xx unknown
-
1995
- 1995-04-03 NO NO19951281A patent/NO310414B1/no not_active IP Right Cessation
- 1995-04-04 FI FI951590A patent/FI109797B/fi not_active IP Right Cessation
- 1995-06-07 US US08/481,208 patent/US5736366A/en not_active Expired - Lifetime
-
1997
- 1997-01-09 GR GR960402652T patent/GR3022229T3/el unknown
- 1997-12-15 CZ CZ19974038A patent/CZ286593B6/cs not_active IP Right Cessation
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4814470A (en) | 1986-07-17 | 1989-03-21 | Rhone-Poulenc Sante | Taxol derivatives, their preparation and pharmaceutical compositions containing them |
| US4857653A (en) | 1986-07-17 | 1989-08-15 | Rhone-Poulenc Sante | Process for the preparation of taxol and 10-deacetyltaxol |
| US4924012A (en) | 1988-04-06 | 1990-05-08 | Rhone-Poulenc Sante | Process for preparing derivatives of baccatine III and of 10-deacetyl baccatine III |
| EP0400971A2 (en) | 1989-05-31 | 1990-12-05 | Florida State University | Method for preparation of taxol |
| EP0428376A1 (en) | 1989-11-14 | 1991-05-22 | Florida State University | Method for preparation of taxol using an oxazinone |
| WO1992007842A1 (en) | 1990-11-02 | 1992-05-14 | University Of Florida | Method for the isolation and purification of taxane derivatives |
| WO1992009589A1 (fr) | 1990-11-23 | 1992-06-11 | Rhone-Poulenc Rorer S.A. | Procede de preparation de derives du taxane, nouveaux derives obtenus et compositions pharmaceutiques qui les contiennent |
Non-Patent Citations (1)
| Title |
|---|
| HUANG CH ET AL.: "New taxanes from Taxus brevifolia, 2.", J NAT PROD., 1986, pages 665 - 669 |
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