NO310413B1 - Fremgangsmåte for fremstilling av 10-desacetyl-baccatin-III - Google Patents
Fremgangsmåte for fremstilling av 10-desacetyl-baccatin-III Download PDFInfo
- Publication number
- NO310413B1 NO310413B1 NO19951282A NO951282A NO310413B1 NO 310413 B1 NO310413 B1 NO 310413B1 NO 19951282 A NO19951282 A NO 19951282A NO 951282 A NO951282 A NO 951282A NO 310413 B1 NO310413 B1 NO 310413B1
- Authority
- NO
- Norway
- Prior art keywords
- baccatin
- desacetyl
- iii
- taxus
- aliphatic
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 24
- YWLXLRUDGLRYDR-SKXCCXORSA-N 10-dab iii Chemical compound O([C@H]1C2[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-SKXCCXORSA-N 0.000 title claims description 57
- 241001116500 Taxus Species 0.000 claims abstract description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 35
- 239000000243 solution Substances 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 239000012675 alcoholic extract Substances 0.000 claims description 17
- 239000003960 organic solvent Substances 0.000 claims description 17
- 238000001914 filtration Methods 0.000 claims description 16
- -1 aliphatic nitriles Chemical class 0.000 claims description 15
- 239000000284 extract Substances 0.000 claims description 14
- 238000010908 decantation Methods 0.000 claims description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 11
- 238000005119 centrifugation Methods 0.000 claims description 10
- 238000004821 distillation Methods 0.000 claims description 9
- 241001116498 Taxus baccata Species 0.000 claims description 8
- 241000202349 Taxus brevifolia Species 0.000 claims description 8
- 235000009065 Taxus cuspidata Nutrition 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- 241000015728 Taxus canadensis Species 0.000 claims description 6
- 241001330449 Taxus wallichiana Species 0.000 claims description 6
- 241001674343 Taxus x media Species 0.000 claims description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 150000002170 ethers Chemical class 0.000 claims description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 238000010790 dilution Methods 0.000 claims description 5
- 239000012895 dilution Substances 0.000 claims description 5
- 239000012074 organic phase Substances 0.000 claims description 5
- 239000012071 phase Substances 0.000 claims description 5
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000008346 aqueous phase Substances 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- 238000007865 diluting Methods 0.000 claims description 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
- 239000000401 methanolic extract Substances 0.000 abstract description 7
- 238000000605 extraction Methods 0.000 abstract description 4
- 238000010956 selective crystallization Methods 0.000 abstract description 4
- 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 2
- 235000013311 vegetables Nutrition 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 20
- 229930012538 Paclitaxel Natural products 0.000 description 13
- 229960001592 paclitaxel Drugs 0.000 description 13
- 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 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- 239000012141 concentrate Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product 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
- 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 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-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
- 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 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 229940063683 taxotere Drugs 0.000 description 4
- NUMQCACRALPSHD-UHFFFAOYSA-N tert-butyl ethyl ether Chemical compound CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 3
- 229940011051 isopropyl acetate Drugs 0.000 description 3
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 3
- RQUBQBFVDOLUKC-UHFFFAOYSA-N 1-ethoxy-2-methylpropane Chemical compound CCOCC(C)C RQUBQBFVDOLUKC-UHFFFAOYSA-N 0.000 description 2
- ZXHQLEQLZPJIFG-UHFFFAOYSA-N 1-ethoxyhexane Chemical compound CCCCCCOCC ZXHQLEQLZPJIFG-UHFFFAOYSA-N 0.000 description 2
- CXBDYQVECUFKRK-UHFFFAOYSA-N 1-methoxybutane Chemical compound CCCCOC CXBDYQVECUFKRK-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- HNFSPSWQNZVCTB-UHFFFAOYSA-N 2-methyl-2-propan-2-yloxypropane Chemical compound CC(C)OC(C)(C)C HNFSPSWQNZVCTB-UHFFFAOYSA-N 0.000 description 2
- FITVQUMLGWRKKG-UHFFFAOYSA-N 2-methyl-2-propoxypropane Chemical compound CCCOC(C)(C)C FITVQUMLGWRKKG-UHFFFAOYSA-N 0.000 description 2
- JCCIFDCPHCKATH-UHFFFAOYSA-N 2-methylbutan-2-yl acetate Chemical compound CCC(C)(C)OC(C)=O JCCIFDCPHCKATH-UHFFFAOYSA-N 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229930014667 baccatin III Natural products 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 229940093499 ethyl acetate Drugs 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- DXBOTVWRXLQVMG-UHFFFAOYSA-N methyl 3,3-dimethylbutanoate Chemical compound COC(=O)CC(C)(C)C DXBOTVWRXLQVMG-UHFFFAOYSA-N 0.000 description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- 238000005325 percolation Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229940090181 propyl acetate Drugs 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- JAELLLITIZHOGQ-UHFFFAOYSA-N tert-butyl propanoate Chemical compound CCC(=O)OC(C)(C)C JAELLLITIZHOGQ-UHFFFAOYSA-N 0.000 description 2
- 238000010257 thawing Methods 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- AOPDRZXCEAKHHW-UHFFFAOYSA-N 1-pentoxypentane Chemical compound CCCCCOCCCCC AOPDRZXCEAKHHW-UHFFFAOYSA-N 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- 208000008839 Kidney Neoplasms Diseases 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
- 206010028980 Neoplasm Diseases 0.000 description 1
- 206010033128 Ovarian cancer Diseases 0.000 description 1
- 206010061535 Ovarian neoplasm Diseases 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 206010038389 Renal cancer Diseases 0.000 description 1
- 208000005718 Stomach Neoplasms Diseases 0.000 description 1
- 229940123237 Taxane Drugs 0.000 description 1
- 241000013869 Taxus floridana Species 0.000 description 1
- 208000024313 Testicular Neoplasms Diseases 0.000 description 1
- 206010057644 Testis cancer Diseases 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000217 alkyl 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
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 150000001602 bicycloalkyls Chemical group 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 239000000287 crude extract Substances 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000010981 drying operation Methods 0.000 description 1
- 239000008394 flocculating agent Substances 0.000 description 1
- 206010017758 gastric cancer Diseases 0.000 description 1
- 239000011491 glass wool Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000000399 hydroalcoholic extract Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 201000010982 kidney cancer Diseases 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 201000011549 stomach cancer Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 201000003120 testicular cancer Diseases 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000005406 washing 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epoxy Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Peptides Or Proteins (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pyrane Compounds (AREA)
- Fats And Perfumes (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)
- Compounds Of Unknown Constitution (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9211746A FR2696463B1 (fr) | 1992-10-05 | 1992-10-05 | Procédé d'obtention de la désacétyl-10 baccatine III. |
PCT/FR1993/000972 WO1994007882A1 (fr) | 1992-10-05 | 1993-10-04 | Procede d'obtention de la desacetyl-10 baccatine iii |
Publications (3)
Publication Number | Publication Date |
---|---|
NO951282D0 NO951282D0 (no) | 1995-04-03 |
NO951282L NO951282L (no) | 1995-04-03 |
NO310413B1 true NO310413B1 (no) | 2001-07-02 |
Family
ID=9434124
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO19951282A NO310413B1 (no) | 1992-10-05 | 1995-04-03 | Fremgangsmåte for fremstilling av 10-desacetyl-baccatin-III |
Country Status (30)
Country | Link |
---|---|
US (1) | US5393895A (sk) |
EP (1) | EP0663910B1 (sk) |
JP (1) | JP3299754B2 (sk) |
KR (1) | KR100301236B1 (sk) |
CN (1) | CN1043530C (sk) |
AT (1) | ATE148883T1 (sk) |
AU (1) | AU680629B2 (sk) |
CA (1) | CA2146373C (sk) |
CZ (2) | CZ284615B6 (sk) |
DE (1) | DE69308155T2 (sk) |
DK (1) | DK0663910T3 (sk) |
EE (1) | EE03126B1 (sk) |
ES (1) | ES2098061T3 (sk) |
FI (1) | FI109794B (sk) |
FR (1) | FR2696463B1 (sk) |
GE (1) | GEP20001937B (sk) |
GR (1) | GR3022617T3 (sk) |
HU (1) | HU226862B1 (sk) |
LT (1) | LT3398B (sk) |
LV (1) | LV10621B (sk) |
MX (1) | MX9305771A (sk) |
NO (1) | NO310413B1 (sk) |
NZ (1) | NZ256450A (sk) |
PL (1) | PL177316B1 (sk) |
RU (1) | RU2107065C1 (sk) |
SK (1) | SK280949B6 (sk) |
TW (1) | TW255890B (sk) |
UA (1) | UA44227C2 (sk) |
WO (1) | WO1994007882A1 (sk) |
ZA (1) | ZA937313B (sk) |
Families Citing this family (74)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2696462B1 (fr) * | 1992-10-05 | 1994-11-25 | Rhone Poulenc Rorer Sa | Procédé d'obtention de la désacétyl-10 baccatine III. |
DE69435141D1 (de) | 1993-07-19 | 2008-10-30 | Angiotech Pharm Inc | Anti-angiogene Mittel und Verfahren zu deren Verwendung |
ES2144533T3 (es) * | 1993-11-02 | 2000-06-16 | Rhone Poulenc Rorer Gmbh | Procedimiento para la separacion de una mezcla. |
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 |
AU716005B2 (en) | 1995-06-07 | 2000-02-17 | Cook Medical Technologies Llc | Implantable medical device |
FR2736355B1 (fr) * | 1995-07-07 | 1997-11-07 | Pf Medicament | Procede d'extraction et d'isolement de la 10-desacetylbaccatine iii |
US5750736A (en) * | 1996-07-11 | 1998-05-12 | Napro Biotherapeutics, Inc. | Method for acylating 10-deacetylbaccatin III selectively at the c-10 position |
US5965752A (en) * | 1996-08-23 | 1999-10-12 | Institut National De La Recherche Scientifique | Preparative scale isolation and purification of taxanes |
EP1019347B1 (en) | 1997-08-21 | 2003-03-19 | Florida State University | Method for the synthesis of taxanes |
US6002024A (en) * | 1998-07-27 | 1999-12-14 | Dabur Research Foundation | Process for the isolation of 14β-hydroxy-10-deacetyl baccatin-III |
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 |
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 |
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 |
CA2307393A1 (en) | 2000-05-01 | 2001-11-01 | The University Of British Columbia | Ginsenoside chemotherapy |
CA2440935A1 (en) | 2001-03-13 | 2002-09-19 | Richard Liggins | Micellar drug delivery vehicles and precursors thereto and uses thereof |
US20030157170A1 (en) * | 2001-03-13 | 2003-08-21 | 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 |
AU2003300076C1 (en) | 2002-12-30 | 2010-03-04 | Angiotech International Ag | Drug delivery from rapid gelling polymer composition |
EP2390262A1 (en) | 2003-05-16 | 2011-11-30 | Intermune, Inc. | Synthetic chemokine receptor ligands and methods of use thereof |
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 |
US7846940B2 (en) | 2004-03-31 | 2010-12-07 | Cordis Corporation | Solution formulations of sirolimus and its analogs for CAD treatment |
WO2006014345A1 (en) * | 2004-07-02 | 2006-02-09 | Ivax Pharmaceuticals S.R.O. | Process for the separation of paclitaxel and cephalomannin |
US7597884B2 (en) | 2004-08-09 | 2009-10-06 | Alios Biopharma, Inc. | Hyperglycosylated polypeptide variants and methods of use |
US8691780B2 (en) | 2005-02-17 | 2014-04-08 | The Board Of Trustees Of The Leland Stanford Junior University | Txr1 and enhanced taxane sensitivity based on the modulation of a pathway mediated thereby |
WO2007062036A2 (en) | 2005-11-21 | 2007-05-31 | Med Institute, Inc. | Implantable medical device coatings with biodegradable elastomer and releasable therapeutic agent |
CA2922029C (en) | 2006-03-22 | 2017-11-28 | Medigene Ag | A combination of a cationic liposomal preparation comprising an antimitotic agent and a non-liposomal preparation comprising an antimitotic agent |
ATE519511T1 (de) | 2006-06-30 | 2011-08-15 | Cook Inc | Verfahren zur herstellung und modifizierung von taxan-beschichtungen für implantierbare medizinische vorrichtungen |
US8409601B2 (en) | 2008-03-31 | 2013-04-02 | Cordis Corporation | Rapamycin coated expandable devices |
US8420110B2 (en) | 2008-03-31 | 2013-04-16 | Cordis Corporation | Drug coated expandable devices |
US8273404B2 (en) | 2008-05-19 | 2012-09-25 | Cordis Corporation | Extraction of solvents from drug containing polymer reservoirs |
ES2530462T3 (es) | 2008-05-22 | 2015-03-03 | Galera Therapeutics Llc | Combinación terapia antitumoral |
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 |
CN104039771B (zh) | 2011-09-26 | 2017-10-27 | Kabi费森尤斯肿瘤学有限公司 | 包括c(7)‑oh和c(13)‑oh甲硅烷基化或仅c(7)‑oh甲硅烷基化的用于制备卡巴他赛的方法 |
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 |
EP2916835A4 (en) | 2012-11-12 | 2016-07-27 | Redwood Bioscience Inc | COMPOUNDS AND METHOD FOR PRODUCING A CONJUGATE |
CN103804326A (zh) * | 2012-11-15 | 2014-05-21 | 刘胜远 | 一种从含10-去乙酰基巴卡亭ⅲ的浸膏分离和提纯10-去乙酰基巴卡亭ⅲ的方法 |
PL2956175T3 (pl) | 2013-02-15 | 2018-05-30 | The Regents Of The University Of California | Chimeryczny receptor antygenowy i sposoby jego zastosowania |
CN103145652B (zh) * | 2013-03-05 | 2015-09-30 | 无锡尔云科技有限公司 | 一种从红豆杉属植物中提取紫杉醇及其衍生物的方法 |
EP2970124B1 (en) | 2013-03-14 | 2019-05-22 | The Board of Trustees of the Leland Stanford Junior University | Mitochondrial aldehyde dehydrogenase-2 modulators and methods of use thereof |
WO2015081282A1 (en) | 2013-11-27 | 2015-06-04 | Redwood Bioscience, Inc. | Hydrazinyl-pyrrolo compounds and methods for producing a conjugate |
EP3107899B1 (en) | 2014-02-19 | 2020-08-12 | Aviv Therapeutics, Inc. | Mitochondrial aldehyde dehydrogenase 2 (aldh2) binding polycyclic amides and their use for the treatment of cancer |
AU2016326747A1 (en) | 2015-09-25 | 2018-03-01 | Zy Therapeutics Inc. | Drug formulation based on particulates comprising polysaccharide-vitamin conjugate |
WO2017083637A1 (en) | 2015-11-12 | 2017-05-18 | The Board Of Trustees Of The Leland Stanford Junior University | Cell-penetrating, guanidinium-rich oligophosphotriesters for drug and probe delivery |
TWI760319B (zh) | 2015-12-30 | 2022-04-11 | 杏國新藥股份有限公司 | 乳癌治療 |
CN109071634A (zh) | 2016-04-26 | 2018-12-21 | R.P.谢勒技术有限责任公司 | 抗体偶联物及其制备和使用方法 |
EP3463308B1 (en) | 2016-06-01 | 2021-12-01 | Servier IP UK Limited | Formulations of polyalkylene oxide-asparaginase and methods of making and using the same |
TW201825087A (zh) | 2017-01-05 | 2018-07-16 | 杏國新藥股份有限公司 | 胰臟癌治療 |
AU2018211081A1 (en) | 2017-01-18 | 2019-07-18 | Bioatla, Inc. | Chimeric antigen receptors against Axl or Ror2 and methods of use thereof |
EP3388082A1 (en) | 2017-04-13 | 2018-10-17 | Galera Labs, LLC | Combination cancer immunotherapy with pentaaza macrocyclic ring complex |
CA3090129A1 (en) | 2018-01-31 | 2019-08-08 | Galera Labs, Llc | Combination cancer therapy with pentaaza macrocyclic ring complex and platinum-based anticancer agent |
US11660266B2 (en) | 2018-04-11 | 2023-05-30 | Ohio State Innovation Foundation | Methods and compositions for sustained release microparticles for ocular drug delivery |
CN108904137A (zh) * | 2018-05-27 | 2018-11-30 | 肖军威 | 一种卫生巾芯片的制备方法及卫生巾芯片的加工设备 |
EP3823674A4 (en) | 2018-07-18 | 2022-12-28 | Manzanita Pharmaceuticals, Inc. | CONJUGATES FOR DELIVERING AN ANTI-CANCER AGENT TO NERVE CELLS, METHODS OF USE AND METHODS OF PRODUCTION THEREOF |
US11529402B2 (en) | 2019-01-14 | 2022-12-20 | 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 |
CN113692413A (zh) | 2019-04-02 | 2021-11-23 | 肯乔克蒂生物技术股份有限公司 | 外排泵-癌症抗原多特异性抗体以及与其相关的组合物、试剂、试剂盒和方法 |
CN110317183B (zh) * | 2019-08-08 | 2021-03-12 | 无锡紫杉药业有限公司 | 一种红豆杉天然提取产物的纯化方法 |
CA3163805A1 (en) | 2019-12-12 | 2021-06-17 | Ignite Immunotherapy, Inc. | Variant oncolytic vaccinia virus and methods of use thereof |
JP2023512196A (ja) | 2020-01-29 | 2023-03-24 | ケンジョッケティ バイオテクノロジー,インク. | 抗mdr1抗体およびその使用 |
AU2021283080A1 (en) | 2020-06-04 | 2022-12-15 | Kenjockety Biotechnology, Inc. | ABCG2 efflux pump-cancer antigen multi-specific antibodies and compositions, reagents, kits and methods related thereto |
WO2021247426A1 (en) | 2020-06-04 | 2021-12-09 | Kenjockety Biotechnology, Inc. | Anti-abcg2 antibodies and uses thereof |
BR112023000650A2 (pt) | 2020-07-14 | 2023-01-31 | Pfizer | Vírus vaccinia recombinante |
CN116490522A (zh) | 2020-09-02 | 2023-07-25 | 肯乔克蒂生物技术股份有限公司 | 抗abcc1抗体及其应用 |
AU2021380659A1 (en) | 2020-11-13 | 2023-06-01 | Kenjockety Biotechnology, Inc. | 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 |
WO2023114658A1 (en) | 2021-12-13 | 2023-06-22 | Kenjockety Biotechnology, Inc. | Anti-abcb1 antibodies |
WO2023159220A1 (en) | 2022-02-18 | 2023-08-24 | Kenjockety Biotechnology, Inc. | Anti-cd47 antibodies |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2601675B1 (fr) * | 1986-07-17 | 1988-09-23 | Rhone Poulenc Sante | Derives du taxol, leur preparation et les compositions pharmaceutiques qui les contiennent |
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 |
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 |
US5380916A (en) | 1990-11-02 | 1995-01-10 | University Of Florida | Method for the isolation and purification of taxane derivatives |
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 |
ATE180477T1 (de) * | 1991-04-19 | 1999-06-15 | Univ Mississippi | Verfahren und zubereitungen zur isolierung von taxanen |
IT1258838B (it) | 1992-01-31 | 1996-02-29 | Indena Spa | Processo per l'estrazione di tassolo e derivati da cultivar del genere taxus |
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