DE102007016046A1 - Verfahren zur Herstellung von Epothilonderivaten durch selektive katalytische Epoxidierung - Google Patents
Verfahren zur Herstellung von Epothilonderivaten durch selektive katalytische Epoxidierung Download PDFInfo
- Publication number
- DE102007016046A1 DE102007016046A1 DE102007016046A DE102007016046A DE102007016046A1 DE 102007016046 A1 DE102007016046 A1 DE 102007016046A1 DE 102007016046 A DE102007016046 A DE 102007016046A DE 102007016046 A DE102007016046 A DE 102007016046A DE 102007016046 A1 DE102007016046 A1 DE 102007016046A1
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- 238000000034 method Methods 0.000 title claims abstract description 52
- 150000003883 epothilone derivatives Chemical class 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 238000006735 epoxidation reaction Methods 0.000 title description 11
- 230000003197 catalytic effect Effects 0.000 title description 2
- VZSXFJPZOCRDPW-UHFFFAOYSA-N carbanide;trioxorhenium Chemical class [CH3-].O=[Re](=O)=O VZSXFJPZOCRDPW-UHFFFAOYSA-N 0.000 claims abstract description 19
- 150000003222 pyridines Chemical class 0.000 claims abstract description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 26
- 239000002904 solvent Substances 0.000 claims description 19
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 18
- 229910052702 rhenium Inorganic materials 0.000 claims description 18
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 15
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 10
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- GPHQHTOMRSGBNZ-UHFFFAOYSA-N pyridine-4-carbonitrile Chemical group N#CC1=CC=NC=C1 GPHQHTOMRSGBNZ-UHFFFAOYSA-N 0.000 claims description 8
- 230000035484 reaction time Effects 0.000 claims description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 5
- 239000000010 aprotic solvent Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 3
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 229930013356 epothilone Natural products 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- HESCAJZNRMSMJG-KKQRBIROSA-N epothilone A Chemical compound C/C([C@@H]1C[C@@H]2O[C@@H]2CCC[C@@H]([C@@H]([C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1)O)C)=C\C1=CSC(C)=N1 HESCAJZNRMSMJG-KKQRBIROSA-N 0.000 description 5
- 150000002118 epoxides Chemical class 0.000 description 5
- 239000012467 final product Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 229930012538 Paclitaxel Natural products 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 229960001592 paclitaxel Drugs 0.000 description 4
- 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 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 150000001541 aziridines Chemical class 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- FFHWGQQFANVOHV-UHFFFAOYSA-N dimethyldioxirane Chemical compound CC1(C)OO1 FFHWGQQFANVOHV-UHFFFAOYSA-N 0.000 description 3
- HESCAJZNRMSMJG-HGYUPSKWSA-N epothilone A Natural products O=C1[C@H](C)[C@H](O)[C@H](C)CCC[C@H]2O[C@H]2C[C@@H](/C(=C\c2nc(C)sc2)/C)OC(=O)C[C@H](O)C1(C)C HESCAJZNRMSMJG-HGYUPSKWSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- QXRSDHAAWVKZLJ-OXZHEXMSSA-N Epothilone B Natural products O=C1[C@H](C)[C@H](O)[C@@H](C)CCC[C@@]2(C)O[C@H]2C[C@@H](/C(=C\c2nc(C)sc2)/C)OC(=O)C[C@H](O)C1(C)C QXRSDHAAWVKZLJ-OXZHEXMSSA-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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000021615 conjugation Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- QXRSDHAAWVKZLJ-PVYNADRNSA-N epothilone B Chemical compound C/C([C@@H]1C[C@@H]2O[C@]2(C)CCC[C@@H]([C@@H]([C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1)O)C)=C\C1=CSC(C)=N1 QXRSDHAAWVKZLJ-PVYNADRNSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 2
- BUHVIAUBTBOHAG-FOYDDCNASA-N (2r,3r,4s,5r)-2-[6-[[2-(3,5-dimethoxyphenyl)-2-(2-methylphenyl)ethyl]amino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound COC1=CC(OC)=CC(C(CNC=2C=3N=CN(C=3N=CN=2)[C@H]2[C@@H]([C@H](O)[C@@H](CO)O2)O)C=2C(=CC=CC=2)C)=C1 BUHVIAUBTBOHAG-FOYDDCNASA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical class C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- ZHGNHOOVYPHPNJ-UHFFFAOYSA-N Amigdalin Chemical compound FC(F)(F)C(=O)OCC1OC(OCC2OC(OC(C#N)C3=CC=CC=C3)C(OC(=O)C(F)(F)F)C(OC(=O)C(F)(F)F)C2OC(=O)C(F)(F)F)C(OC(=O)C(F)(F)F)C(OC(=O)C(F)(F)F)C1OC(=O)C(F)(F)F ZHGNHOOVYPHPNJ-UHFFFAOYSA-N 0.000 description 1
- BMZPYCYOLYELTH-SRFOJHRASA-M CC(CCC[C@H](C)C[C@@H](CC=C)C(C(C)(C)[C@H](CC([O-])=O)O)=O)CCCc(cc1)cc2c1[s]c(C)n2 Chemical compound CC(CCC[C@H](C)C[C@@H](CC=C)C(C(C)(C)[C@H](CC([O-])=O)O)=O)CCCc(cc1)cc2c1[s]c(C)n2 BMZPYCYOLYELTH-SRFOJHRASA-M 0.000 description 1
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- BFZKMNSQCNVFGM-UCEYFQQTSA-N Sagopilone Chemical compound O1C(=O)C[C@H](O)C(C)(C)C(=O)[C@H](CC=C)[C@@H](O)[C@@H](C)CCC[C@@]2(C)O[C@H]2C[C@H]1C1=CC=C(SC(C)=N2)C2=C1 BFZKMNSQCNVFGM-UCEYFQQTSA-N 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
- 229940123237 Taxane Drugs 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- -1 and aqueous Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000007321 biological mechanism Effects 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000002354 inductively-coupled plasma atomic emission spectroscopy Methods 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000011020 pilot scale process Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007016046A DE102007016046A1 (de) | 2007-03-30 | 2007-03-30 | Verfahren zur Herstellung von Epothilonderivaten durch selektive katalytische Epoxidierung |
| KR1020097020329A KR20090125259A (ko) | 2007-03-30 | 2008-03-27 | 선택적 촉매 에폭시화에 의한 에포틸론 유도체의 제조 방법 |
| UY30985A UY30985A1 (es) | 2007-03-30 | 2008-03-27 | Procedimiento para la preparacion de derivados de epotilona por epoxidacion catalitica selectiva. |
| PCT/EP2008/002652 WO2008119563A2 (de) | 2007-03-30 | 2008-03-27 | Verfahren zur herstellung von epothilonderivaten durch selektive katalytische epoxidierung |
| US12/056,393 US20080242868A1 (en) | 2007-03-30 | 2008-03-27 | Process for preparing epothilone derivatives by selective catalytic epoxidation |
| CA002681806A CA2681806A1 (en) | 2007-03-30 | 2008-03-27 | Process for preparing epothilone derivatives by selective catalytic epoxidation |
| EP08734992A EP2142539A2 (de) | 2007-03-30 | 2008-03-27 | Verfahren zur herstellung von epothilonderivaten durch selektive katalytische epoxidierung |
| JP2010500148A JP2010523481A (ja) | 2007-03-30 | 2008-03-27 | 選択的触媒的エポキシ化によるエポチロン誘導体の製造方法 |
| CN2008800103886A CN101652362B (zh) | 2007-03-30 | 2008-03-27 | 通过选择性催化环氧化反应制备埃坡霉素衍生物的方法 |
| CL200800901A CL2008000901A1 (es) | 2007-03-30 | 2008-03-28 | Procedimiento para preparar un derivado de epotilona, usando piridinas sustituidas y metiltrioxorenio como catalizador; y un derivado de epotilona que contiene renio. |
| PA20088773901A PA8773901A1 (es) | 2007-03-30 | 2008-03-28 | Procedimiento para la preparación de derivados de epotilona por epoxidación catalítica selectiva |
| ARP080101279A AR066692A1 (es) | 2007-03-30 | 2008-03-28 | Procedimiento para la preparacion de derivados de epotilona por eepoxidacion catalitica selectiva |
| TW097111589A TW200902538A (en) | 2007-03-30 | 2008-03-28 | Process for preparing epothilone derivatives by selective catalytic epoxidation |
| US13/308,046 US8314248B2 (en) | 2007-03-30 | 2011-11-30 | Process for preparing epothilone derivatives by selective catalytic epoxidation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007016046A DE102007016046A1 (de) | 2007-03-30 | 2007-03-30 | Verfahren zur Herstellung von Epothilonderivaten durch selektive katalytische Epoxidierung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE102007016046A1 true DE102007016046A1 (de) | 2008-10-23 |
Family
ID=39551678
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE102007016046A Withdrawn DE102007016046A1 (de) | 2007-03-30 | 2007-03-30 | Verfahren zur Herstellung von Epothilonderivaten durch selektive katalytische Epoxidierung |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US20080242868A1 (https=) |
| EP (1) | EP2142539A2 (https=) |
| JP (1) | JP2010523481A (https=) |
| KR (1) | KR20090125259A (https=) |
| CN (1) | CN101652362B (https=) |
| AR (1) | AR066692A1 (https=) |
| CA (1) | CA2681806A1 (https=) |
| CL (1) | CL2008000901A1 (https=) |
| DE (1) | DE102007016046A1 (https=) |
| PA (1) | PA8773901A1 (https=) |
| TW (1) | TW200902538A (https=) |
| UY (1) | UY30985A1 (https=) |
| WO (1) | WO2008119563A2 (https=) |
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| CN114539143A (zh) * | 2022-01-28 | 2022-05-27 | 安徽瑞邦生物科技有限公司 | 一种4-氰基吡啶的纯化方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000037473A1 (en) | 1998-12-22 | 2000-06-29 | Novartis Ag | Epothilone derivatives and their use as antitumor agents |
| WO2000066589A1 (en) | 1999-04-30 | 2000-11-09 | Schering Aktiengesellschaft | 6-alkenyl-, 6-alkinyl- and 6-epoxy-epothilone derivatives, process for their production, and their use in pharmaceutical preparations |
| WO2005090335A1 (en) * | 2004-03-16 | 2005-09-29 | Novartis Ag | Epothilone derivatives |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1340498A1 (en) * | 2002-03-01 | 2003-09-03 | Schering Aktiengesellschaft | Use of epothilones in the treatment of brain diseases associated with proliferative processes |
-
2007
- 2007-03-30 DE DE102007016046A patent/DE102007016046A1/de not_active Withdrawn
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2008
- 2008-03-27 US US12/056,393 patent/US20080242868A1/en not_active Abandoned
- 2008-03-27 CA CA002681806A patent/CA2681806A1/en not_active Abandoned
- 2008-03-27 KR KR1020097020329A patent/KR20090125259A/ko not_active Withdrawn
- 2008-03-27 UY UY30985A patent/UY30985A1/es not_active Application Discontinuation
- 2008-03-27 CN CN2008800103886A patent/CN101652362B/zh not_active Expired - Fee Related
- 2008-03-27 WO PCT/EP2008/002652 patent/WO2008119563A2/de not_active Ceased
- 2008-03-27 JP JP2010500148A patent/JP2010523481A/ja not_active Withdrawn
- 2008-03-27 EP EP08734992A patent/EP2142539A2/de not_active Withdrawn
- 2008-03-28 PA PA20088773901A patent/PA8773901A1/es unknown
- 2008-03-28 TW TW097111589A patent/TW200902538A/zh unknown
- 2008-03-28 AR ARP080101279A patent/AR066692A1/es not_active Application Discontinuation
- 2008-03-28 CL CL200800901A patent/CL2008000901A1/es unknown
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2011
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000037473A1 (en) | 1998-12-22 | 2000-06-29 | Novartis Ag | Epothilone derivatives and their use as antitumor agents |
| DE69910831T2 (de) * | 1998-12-22 | 2004-07-15 | Novartis Ag | Epothilonderivate und ihre verwendung als antitumormittel |
| WO2000066589A1 (en) | 1999-04-30 | 2000-11-09 | Schering Aktiengesellschaft | 6-alkenyl-, 6-alkinyl- and 6-epoxy-epothilone derivatives, process for their production, and their use in pharmaceutical preparations |
| WO2005090335A1 (en) * | 2004-03-16 | 2005-09-29 | Novartis Ag | Epothilone derivatives |
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Also Published As
| Publication number | Publication date |
|---|---|
| TW200902538A (en) | 2009-01-16 |
| CA2681806A1 (en) | 2008-10-09 |
| US8314248B2 (en) | 2012-11-20 |
| EP2142539A2 (de) | 2010-01-13 |
| KR20090125259A (ko) | 2009-12-04 |
| UY30985A1 (es) | 2008-10-31 |
| US20080242868A1 (en) | 2008-10-02 |
| PA8773901A1 (es) | 2008-11-19 |
| JP2010523481A (ja) | 2010-07-15 |
| AR066692A1 (es) | 2009-09-09 |
| CN101652362B (zh) | 2012-10-10 |
| CN101652362A (zh) | 2010-02-17 |
| WO2008119563A2 (de) | 2008-10-09 |
| WO2008119563A3 (de) | 2009-02-12 |
| CL2008000901A1 (es) | 2008-10-17 |
| US20120077984A1 (en) | 2012-03-29 |
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