NO309089B1 - FremgangsmÕte for fremstilling av taxanderivater - Google Patents

FremgangsmÕte for fremstilling av taxanderivater Download PDF

Info

Publication number: NO309089B1
Authority: NO; Norway
Prior art keywords: general formula; aliphatic; compound; optionally; indicated above
Prior art date: 1992-10-05

Application number

NO951201A

Other languages

English (en)

Norwegian (no)

Other versions

NO951201D0 (no

NO951201L (no

Inventor

Jean-Manuel Mas

Viviane Massonneau

Original Assignee

Rhone Poulenc Rorer Sa

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1992-10-05

Filing date

1995-03-29

Publication date

2000-12-11

1995-03-29 Application filed by Rhone Poulenc Rorer Sa filed Critical Rhone Poulenc Rorer Sa

1995-03-29 Publication of NO951201D0 publication Critical patent/NO951201D0/no

1995-03-29 Publication of NO951201L publication Critical patent/NO951201L/no

2000-12-11 Publication of NO309089B1 publication Critical patent/NO309089B1/no

Links

238000000034 method Methods 0.000 title claims abstract 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 title claims description 3
239000002253 acid Substances 0.000 claims abstract description 17
125000006239 protecting group Chemical group 0.000 claims abstract description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
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 abstract description 10
150000002148 esters Chemical class 0.000 claims abstract description 8
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract description 6
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 claims abstract description 5
229930014667 baccatin III Natural products 0.000 claims abstract description 5
125000001424 substituent group Chemical group 0.000 claims abstract description 5
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 27
-1 2,2,2-trichloroethoxycarbonyl Chemical group 0.000 claims description 22
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 11
239000003960 organic solvent Substances 0.000 claims description 11
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
125000001931 aliphatic group Chemical group 0.000 claims description 9
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 8
229910052500 inorganic mineral Inorganic materials 0.000 claims description 8
239000011707 mineral Substances 0.000 claims description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 7
239000003795 chemical substances by application Substances 0.000 claims description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
239000011701 zinc Substances 0.000 claims description 7
229910052725 zinc Inorganic materials 0.000 claims description 7
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
229910052802 copper Inorganic materials 0.000 claims description 6
239000010949 copper Substances 0.000 claims description 6
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 5
150000003927 aminopyridines Chemical class 0.000 claims description 5
150000002170 ethers Chemical class 0.000 claims description 5
150000002576 ketones Chemical class 0.000 claims description 5
150000002825 nitriles Chemical class 0.000 claims description 5
150000007524 organic acids Chemical class 0.000 claims description 5
230000003213 activating effect Effects 0.000 claims description 4
150000007530 organic bases Chemical class 0.000 claims description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
150000007522 mineralic acids Chemical class 0.000 claims description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
239000000376 reactant Substances 0.000 claims description 3
150000003512 tertiary amines Chemical class 0.000 claims description 3
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
150000007513 acids Chemical class 0.000 claims description 2
150000001298 alcohols Chemical class 0.000 claims description 2
150000003949 imides Chemical class 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract description 8
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 abstract description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 5
125000000217 alkyl group Chemical group 0.000 abstract description 3
125000003118 aryl group Chemical group 0.000 abstract description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract description 2
125000003342 alkenyl group Chemical group 0.000 abstract 2
125000000753 cycloalkyl group Chemical group 0.000 abstract 2
239000001257 hydrogen Substances 0.000 abstract 2
229910052739 hydrogen Inorganic materials 0.000 abstract 2
230000010933 acylation Effects 0.000 abstract 1
238000005917 acylation reaction Methods 0.000 abstract 1
125000003545 alkoxy group Chemical group 0.000 abstract 1
125000000304 alkynyl group Chemical group 0.000 abstract 1
125000003710 aryl alkyl group Chemical group 0.000 abstract 1
125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
125000000623 heterocyclic group Chemical group 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 29
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 6
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 6
235000010755 mineral Nutrition 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
238000003756 stirring Methods 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
230000032050 esterification Effects 0.000 description 4
238000005886 esterification reaction Methods 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
RGUKYNXWOWSRET-UHFFFAOYSA-N 4-pyrrolidin-1-ylpyridine Chemical compound C1CCCN1C1=CC=NC=C1 RGUKYNXWOWSRET-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
239000002585 base Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000000047 product Substances 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000008096 xylene Substances 0.000 description 3
150000003738 xylenes Chemical class 0.000 description 3
YOWQWFMSQCOSBA-UHFFFAOYSA-N 2-methoxypropene Chemical compound COC(C)=C YOWQWFMSQCOSBA-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000005840 aryl radicals Chemical group 0.000 description 2
125000004104 aryloxy group Chemical group 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
238000009835 boiling Methods 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000007127 saponification reaction Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000002904 solvent Substances 0.000 description 2
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
LJCZNYWLQZZIOS-UHFFFAOYSA-N 2,2,2-trichlorethoxycarbonyl chloride Chemical compound ClC(=O)OCC(Cl)(Cl)Cl LJCZNYWLQZZIOS-UHFFFAOYSA-N 0.000 description 1
HOJZAHQWDXAPDJ-UHFFFAOYSA-N 3-anilino-2-hydroxypropanoic acid Chemical class OC(=O)C(O)CNC1=CC=CC=C1 HOJZAHQWDXAPDJ-UHFFFAOYSA-N 0.000 description 1
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000005107 alkyl diaryl silyl group Chemical group 0.000 description 1
230000000719 anti-leukaemic effect Effects 0.000 description 1
230000000259 anti-tumor effect Effects 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
125000005105 dialkylarylsilyl group Chemical group 0.000 description 1
RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
229910000071 diazene Inorganic materials 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
OQXZCZPHGZPHNR-VHSXEESVSA-N methyl (2r,3s)-2-hydroxy-3-phenyl-3-(2,2,2-trichloroethoxycarbonylamino)propanoate Chemical compound ClC(Cl)(Cl)COC(=O)N[C@H]([C@@H](O)C(=O)OC)C1=CC=CC=C1 OQXZCZPHGZPHNR-VHSXEESVSA-N 0.000 description 1
125000001477 organic nitrogen group Chemical group 0.000 description 1
150000002917 oxazolidines Chemical class 0.000 description 1
239000012071 phase Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229960003975 potassium Drugs 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
125000005106 triarylsilyl group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- 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
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D263/06—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by oxygen atoms, attached to ring carbon atoms
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
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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)
Epoxy Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Plural Heterocyclic Compounds (AREA)

NO951201A 1992-10-05 1995-03-29 FremgangsmÕte for fremstilling av taxanderivater NO309089B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9211741A FR2696458B1 (fr)	1992-10-05	1992-10-05	Procédé de préparation de dérivés du taxane.
PCT/FR1993/000967 WO1994007877A1 (fr)	1992-10-05	1993-10-04	Procede de preparation de derives du taxane

Publications (3)

Publication Number	Publication Date
NO951201D0 NO951201D0 (no)	1995-03-29
NO951201L NO951201L (no)	1995-03-29
NO309089B1 true NO309089B1 (no)	2000-12-11

Family

ID=9434119

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO951201A NO309089B1 (no)	1992-10-05	1995-03-29	FremgangsmÕte for fremstilling av taxanderivater

Country Status (24)

Country	Link
US (3)	US5616739A (de)
EP (1)	EP0663906B1 (de)
JP (1)	JP3014760B2 (de)
KR (1)	KR100311198B1 (de)
AT (1)	ATE146174T1 (de)
AU (1)	AU689080B2 (de)
CA (1)	CA2146250C (de)
CZ (1)	CZ283261B6 (de)
DE (1)	DE69306591T2 (de)
DK (1)	DK0663906T3 (de)
ES (1)	ES2095081T3 (de)
FI (1)	FI109793B (de)
FR (1)	FR2696458B1 (de)
GR (1)	GR3021997T3 (de)
HU (1)	HU226412B1 (de)
MX (1)	MX9305766A (de)
NO (1)	NO309089B1 (de)
NZ (1)	NZ256445A (de)
PL (1)	PL182284B1 (de)
RU (1)	RU2116303C1 (de)
SK (1)	SK280627B6 (de)
TW (1)	TW419472B (de)
WO (1)	WO1994007877A1 (de)
ZA (1)	ZA937318B (de)

Families Citing this family (82)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2696464B1 (fr) *	1992-10-05	1994-11-10	Rhone Poulenc Rorer Sa	Nouveau procédé d'estérification de la baccatine III et de la désacétyl-10 baccatine III.
FR2697522B1 (fr) *	1992-10-30	1994-11-25	Rhone Poulenc Rorer Sa	Procédé de préparation de dérivés du taxane.
FR2698361B1 (fr) *	1992-11-20	1995-01-13	Rhone Poulenc Rorer Sa	Procédé de préparation d'un acide oxazolidine-1,3 carboxylique-5.
IL107950A (en)	1992-12-15	2001-04-30	Upjohn Co	7β, 8β - METHANO-TAXOLS, THEIR PREPARATION AND ANTINEOPLASTIC PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
US5973160A (en) *	1992-12-23	1999-10-26	Poss; Michael A.	Methods for the preparation of novel sidechain-bearing taxanes
ES2205663T3 (es) *	1993-06-11	2004-05-01	PHARMACIA & UPJOHN COMPANY	Uso antineoplasico de delta 6,7-taxoles y composiciones farmaceuticas que los contienen.
FR2706457B1 (fr) *	1993-06-16	1995-07-28	Rhone Poulenc Rorer Sa	Procédé de préparation d'un acide oxazolidinecarboxylique utile pour préparer des taxoïdes thérapeutiquement actifs.
US6005120A (en)	1993-07-20	1999-12-21	Florida State University	Tricyclic and tetracyclic taxanes
KR100354309B1 (ko) *	1993-11-12	2003-01-06	파마시아 앤드 업존 캄파니	피리미딘-티오알킬및알킬에테르화합물
IL127598A (en) *	1994-01-28	2003-04-10	Upjohn Co	Process for preparing isotaxol analogs
US5679807A (en) *	1995-01-30	1997-10-21	Hauser, Inc.	Preparation of taxol and docetaxel through primary amines
CA2170661A1 (en) *	1995-03-22	1996-09-23	John K. Thottathil	Novel methods for the preparation of taxanes using oaxzolidine intermediates
GB9512471D0 (en) *	1995-06-20	1995-08-23	Pharmacia Spa	Method for the preparation of taxol and its derivatives
US5688977A (en) *	1996-02-29	1997-11-18	Napro Biotherapeutics, Inc.	Method for docetaxel synthesis
ATE223889T1 (de) *	1996-05-08	2002-09-15	Upjohn Co	Oxazolidinester
US7288665B1 (en) *	1997-08-18	2007-10-30	Florida State University	Process for selective derivatization of taxanes
US6111144A (en)	1997-08-21	2000-08-29	Florida State University	Method for the synthesis of a taxane intermediate
WO1999032109A1 (en) *	1997-12-23	1999-07-01	Bristol-Myers Squibb Company	7-deoxy-6-nitrogen substituted paclitaxels
AU775373B2 (en)	1999-10-01	2004-07-29	Immunogen, Inc.	Compositions and methods for treating cancer using immunoconjugates and chemotherapeutic agents
CZ2003837A3 (cs) *	2000-09-22	2004-12-15	Bristol-Myers Squibb Company	Způsob pro snížení toxicity při kombinovaných chemoterapiích
US6891050B2 (en) *	2001-08-10	2005-05-10	Dabur India Limited	Process for the preparation of taxanes such as paclitaxel, docetaxel and structurally similar analogs
US6881852B2 (en) *	2002-02-05	2005-04-19	Dabur India Limited	Process of purification of paclitaxel and docetaxel
US7247738B2 (en) *	2002-05-07	2007-07-24	Dabur India Limited	Method of preparation of anticancer taxanes using 3-[(substituted-2-trialkylsilyl) ethoxycarbonyl]-5-oxazolidine carboxylic acids
US6900342B2 (en) *	2002-05-10	2005-05-31	Dabur India Limited	Anticancer taxanes such as paclitaxel, docetaxel and their structural analogs, and a method for the preparation thereof
US7351542B2 (en)	2002-05-20	2008-04-01	The Regents Of The University Of California	Methods of modulating tubulin deacetylase activity
EP1530465B2 (de) *	2002-06-26	2015-12-16	MediGene AG	Herstellung einer kationisch liposomalen zubereitung, einen lipophilen wirkstoff enthaltend
US20040132991A1 (en) *	2002-10-09	2004-07-08	Phytogen Life Sciences Inc.	Novel taxanes and methods related to use and preparation thereof
US6838569B2 (en)	2002-12-16	2005-01-04	Dabur India Limited	Process for preparation of paclitaxel trihydrate and docetaxel trihydrate
CA2525647A1 (en)	2003-05-16	2005-02-24	Intermune, Inc.	Synthetic chemokine receptor ligands and methods of use thereof
US7407973B2 (en) *	2003-10-24	2008-08-05	Intermune, Inc.	Use of pirfenidone in therapeutic regimens
US7202370B2 (en) *	2003-10-27	2007-04-10	Conor Medsystems, Inc.	Semi-synthesis of taxane intermediates from 9-dihydro-13-acetylbaccatin III
US7597884B2 (en) *	2004-08-09	2009-10-06	Alios Biopharma, Inc.	Hyperglycosylated polypeptide variants and methods of use
WO2006020580A2 (en) *	2004-08-09	2006-02-23	Alios Biopharma Inc.	Synthetic hyperglycosylated, protease-resistant polypeptide variants, oral formulations and methods of using the same
EP1647552A1 (de) *	2004-10-08	2006-04-19	INDENA S.p.A.	Teilsynthese für die Herstellung von 10-deacetyl-n-debenzoyl-paclitaxel
US7446126B2 (en)	2004-10-08	2008-11-04	Indena S.P.A.	Semisynthesis process for the preparation of 10-deacetyl-N-debenzoyl-paclitaxel
EP1712552A1 (de) *	2005-04-11	2006-10-18	INDENA S.p.A.	Teilsynthese für die Herstellung von 10-deacetyl-n-debenzoyl-paclitaxel
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
BRPI0709075A2 (pt)	2006-03-20	2011-10-11	Medigene Ag	tratamento de cáncer de mama triplo receptor negativo
EP2001874A4 (de) *	2006-03-21	2010-04-07	Reddys Lab Ltd Dr	Docetaxel-polymorphe und entsprechende verfahren
ITMI20062479A1 (it) *	2006-12-21	2008-06-22	Indena Spa	Processo per la preparazione di secotassani
EP2296645B1 (de)	2008-05-22	2014-11-19	Galera Therapeutics, LLC	Antitumorale kombinationstherapie
KR101003822B1 (ko)	2008-06-20	2010-12-27	주식회사 셀트리온화학연구소	도세탁셀의 제조방법 및 도세탁셀의 제조를 위한 신규한중간체
EP2310507A4 (de)	2008-07-08	2013-03-20	David Gladstone Inst	Verfahren und zusammensetzungen zur angiogenesemodulierung
CN101735179B (zh) *	2008-11-19	2012-09-12	上海百灵医药科技有限公司	一种多烯紫杉醇的制备方法，其中间体及制备方法
EP2358693A4 (de) *	2008-11-20	2012-04-18	Reddys Lab Ltd Dr	Herstellung von docetaxel
PL388144A1 (pl)	2009-05-29	2010-12-06	Przedsiębiorstwo Produkcyjno-Wdrożeniowe Ifotam Spółka Z Ograniczoną Odpowiedzialnością	Solwaty (2R,3S)-3-tert-butoksykarbonylamino-2-hydroksy-3-fenylopropionianu 4-acetoksy-2α-benzoiloksy -5β,20-epoksy-1,7β,10β-trihydroksy-9-okso-taks-11-en-13α-ylu, sposób ich otrzymywania i zastosowanie
EP3539563A1 (de)	2012-07-19	2019-09-18	Redwood Bioscience, Inc.	Für cd22 spezifischer antikörper und verfahren zur verwendung davon
AU2013341711A1 (en)	2012-11-12	2015-05-21	Redwood Bioscience, Inc.	Compounds and methods for producing a conjugate
DK2956175T3 (da)	2013-02-15	2017-11-27	Univ California	Kimærisk antigenreceptor og fremgangsmåder til anvendelse deraf
WO2014160185A2 (en)	2013-03-14	2014-10-02	The Board Of Trustees Of The Leland Stanford Junior University	Mitochondrial aldehyde dehydrogenase-2 modulators and methods of use thereof
CN115504924A (zh)	2013-11-27	2022-12-23	雷德伍德生物科技股份有限公司	肼基-吡咯并化合物及用于生成缀合物的方法
HUE051255T2 (hu)	2014-02-19	2021-03-01	Aviv Therapeutics Inc	Mitokondriális aldehid dehidrogenáz 2 (ALDH2) kötõ policiklusos amidok és alkalmazásuk rák kezelésére
AR099812A1 (es)	2014-03-21	2016-08-17	Abbvie Inc	Anticuerpos y conjugados de anticuerpo y fármaco anti-egfr
US10654875B2 (en)	2015-11-12	2020-05-19	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
EP3231421A1 (de)	2016-04-11	2017-10-18	Greenaltech, S.L.	Verwendungen eines carotenoids bei der behandlung oder prävention von durch stress verursachten störungen
JP2019515677A (ja)	2016-04-26	2019-06-13	アール．ピー．シェーラーテクノロジーズエルエルシー	抗体複合体ならびにそれを作製および使用する方法
CN109640961B (zh)	2016-06-01	2021-11-02	施维雅知识产权英国有限公司	聚亚烷基氧化物-天冬酰胺酶制剂及其制备和使用方法
WO2017214322A1 (en)	2016-06-08	2017-12-14	Abbvie Inc.	Anti-b7-h3 antibodies and antibody drug conjugates
JP2019524651A (ja)	2016-06-08	2019-09-05	アッヴィ・インコーポレイテッド	抗ｃｄ９８抗体及び抗体薬物コンジュゲート
US20200147235A1 (en)	2016-06-08	2020-05-14	Abbvie Inc.	Anti-cd98 antibodies and antibody drug conjugates
MX2018015285A (es)	2016-06-08	2019-09-18	Abbvie Inc	Anticuerpos anti-b7-h3 y conjugados de anticuerpo y farmaco.
AU2017279550A1 (en)	2016-06-08	2019-01-03	Abbvie Inc.	Anti-B7-H3 antibodies and antibody drug conjugates
TWI852903B (zh)	2017-01-05	2024-08-21	杏國新藥股份有限公司	胰臟癌治療
JP7280827B2 (ja)	2017-01-18	2023-05-24	エクスマバイオテックコーポレイション	Ａｘｌまたはｒｏｒ２に対するキメラ抗原受容体およびその使用方法
EP3388082A1 (de)	2017-04-13	2018-10-17	Galera Labs, LLC	Kombinationskrebsimmuntherapie mit makrocyclischem pentaaza-ringkomplex
WO2018218004A1 (en)	2017-05-24	2018-11-29	The Board Of Regents Of The University Of Texas System	Linkers for antibody drug conjugates
CA3090129A1 (en)	2018-01-31	2019-08-08	Galera Labs, Llc	Combination cancer therapy with pentaaza macrocyclic ring complex and platinum-based anticancer agent
CA3096202A1 (en)	2018-04-06	2019-10-10	The Regents Of The University Of California	Methods of treating egfrviii expressing glioblastomas
CA3095757A1 (en)	2018-04-06	2019-10-10	The Regents Of The University Of California	Methods of treating glioblastomas
BR112020020930A2 (pt)	2018-04-11	2021-03-02	Ohio State Innovation Foundation	composição de liberação de fármaco, método para tratar um distúrbio oftalmológico e kit
CA3105879A1 (en)	2018-07-18	2020-01-23	Manzanita Pharmaceuticals, Inc.	Conjugates for delivering an anti-cancer agent to nerve cells, methods of use and methods of making thereof
JP7716623B2 (ja)	2019-04-02	2025-08-01	ウィリアムロバートアラスーンリビングトラストデイテッドオーガスト 29, 2016	排出ポンプ－癌抗原マルチ特異性抗体ならびにそれに関する組成物、試薬、キットおよび方法
WO2021155028A1 (en)	2020-01-29	2021-08-05	Kenjockety Biotechnology, Inc.	Anti-mdr1 antibodies and uses thereof
WO2021247426A1 (en)	2020-06-04	2021-12-09	Kenjockety Biotechnology, Inc.	Anti-abcg2 antibodies and uses thereof
CN116529267A (zh)	2020-06-04	2023-08-01	肯乔克蒂生物技术股份有限公司	Abcg2外排泵-癌症抗原多特异性抗体及其相关组合物、试剂、试剂盒和方法
CA3193588A1 (en)	2020-09-02	2022-03-10	Kenjockety Biotechnology, Inc.	Anti-abcc1 antibodies and uses thereof
WO2022103603A1 (en)	2020-11-13	2022-05-19	Kenjockety Biotechnology, Inc.	Anti-mrp4 (encoded by abcc4 gene) antibodies and uses thereof
US12187810B2 (en)	2020-11-20	2025-01-07	R.P. Scherer Technologies, Llc	Glycoside dual-cleavage linkers for antibody-drug conjugates
AR124681A1 (es)	2021-01-20	2023-04-26	Abbvie Inc	Conjugados anticuerpo-fármaco anti-egfr
US20250051471A1 (en)	2021-12-13	2025-02-13	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

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
US5015744A (en) *	1989-11-14	1991-05-14	Florida State University	Method for preparation of taxol using an oxazinone
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
US5319112A (en) *	1992-08-18	1994-06-07	Virgnia Tech Intellectual Properties, Inc.	Method for the conversion of cephalomannine to taxol and for the preparation of N-acyl analogs of taxol

1992
- 1992-10-05 FR FR9211741A patent/FR2696458B1/fr not_active Expired - Lifetime
1993
- 1993-09-21 MX MX9305766A patent/MX9305766A/es unknown
- 1993-10-01 ZA ZA937318A patent/ZA937318B/xx unknown
- 1993-10-02 TW TW082108117A patent/TW419472B/zh not_active IP Right Cessation
- 1993-10-04 ES ES93921982T patent/ES2095081T3/es not_active Expired - Lifetime
- 1993-10-04 PL PL93308241A patent/PL182284B1/pl unknown
- 1993-10-04 CA CA002146250A patent/CA2146250C/fr not_active Expired - Lifetime
- 1993-10-04 US US08/411,692 patent/US5616739A/en not_active Expired - Lifetime
- 1993-10-04 AT AT93921982T patent/ATE146174T1/de active
- 1993-10-04 CZ CZ95841A patent/CZ283261B6/cs not_active IP Right Cessation
- 1993-10-04 KR KR1019950701302A patent/KR100311198B1/ko not_active Expired - Lifetime
- 1993-10-04 RU RU95113717A patent/RU2116303C1/ru active
- 1993-10-04 HU HU9500971A patent/HU226412B1/hu unknown
- 1993-10-04 SK SK436-95A patent/SK280627B6/sk not_active IP Right Cessation
- 1993-10-04 EP EP93921982A patent/EP0663906B1/de not_active Expired - Lifetime
- 1993-10-04 WO PCT/FR1993/000967 patent/WO1994007877A1/fr not_active Ceased
- 1993-10-04 DK DK93921982.0T patent/DK0663906T3/da active
- 1993-10-04 NZ NZ256445A patent/NZ256445A/en not_active IP Right Cessation
- 1993-10-04 JP JP6508787A patent/JP3014760B2/ja not_active Expired - Lifetime
- 1993-10-04 AU AU51150/93A patent/AU689080B2/en not_active Expired
- 1993-10-04 DE DE69306591T patent/DE69306591T2/de not_active Expired - Lifetime
1995
- 1995-03-29 NO NO951201A patent/NO309089B1/no not_active IP Right Cessation
- 1995-04-04 FI FI951595A patent/FI109793B/fi not_active IP Right Cessation
1996
- 1996-10-31 US US08/742,101 patent/US5677462A/en not_active Expired - Lifetime
- 1996-12-12 GR GR960402201T patent/GR3021997T3/el unknown
1997
- 1997-08-08 US US08/908,806 patent/US5869680A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
NO951201D0 (no)	1995-03-29
US5869680A (en)	1999-02-09
SK43695A3 (en)	1995-08-09
JP3014760B2 (ja)	2000-02-28
DE69306591D1 (de)	1997-01-23
AU5115093A (en)	1994-04-26
GR3021997T3 (en)	1997-03-31
DE69306591T2 (de)	1997-04-17
AU689080B2 (en)	1998-03-26
ES2095081T3 (es)	1997-02-01
MX9305766A (es)	1995-01-31
HUT72679A (en)	1996-05-28
EP0663906B1 (de)	1996-12-11
KR950703546A (ko)	1995-09-20
EP0663906A1 (de)	1995-07-26
CZ84195A3 (en)	1995-09-13
CA2146250C (fr)	2003-03-11
FI951595L (fi)	1995-04-04
FI951595A0 (fi)	1995-04-04
RU95113717A (ru)	1996-12-27
WO1994007877A1 (fr)	1994-04-14
CA2146250A1 (fr)	1994-04-14
FR2696458B1 (fr)	1994-11-10
US5677462A (en)	1997-10-14
SK280627B6 (sk)	2000-05-16
FI109793B (fi)	2002-10-15
DK0663906T3 (da)	1996-12-30
ZA937318B (en)	1994-04-25
FR2696458A1 (fr)	1994-04-08
RU2116303C1 (ru)	1998-07-27
TW419472B (en)	2001-01-21
KR100311198B1 (ko)	2002-04-24
ATE146174T1 (de)	1996-12-15
PL308241A1 (en)	1995-07-24
NZ256445A (en)	1997-01-29
NO951201L (no)	1995-03-29
JPH08501788A (ja)	1996-02-27
PL182284B1 (pl)	2001-12-31
CZ283261B6 (cs)	1998-02-18
US5616739A (en)	1997-04-01
HU226412B1 (en)	2008-11-28
HU9500971D0 (en)	1995-06-28

Legal Events

Date	Code	Title	Description
2013-11-11	MK1K	Patent expired

Publication	Publication Date	Title
NO309089B1 (no)	2000-12-11	FremgangsmÕte for fremstilling av taxanderivater
NO311255B1 (no)	2001-11-05	Fremgangsmåte for fremstilling av taxanderivater samt mellomprodukter til bruk ved fremstillingen
JP3064419B2 (ja)	2000-07-12	バッカチン▲ｉｉｉ▼及び１０−デアセチルバッカチン▲ｉｉｉ▼のエステル化のための新規な方法
NO310412B1 (no)	2001-07-02	Fremgangsmåte for fremstilling av taxanderivater samt syrer og mellomprodukter til bruk ved fremgangsmåten
FI109798B (fi)	2002-10-15	Menetelmä taksaanivälituotteiden valmistamiseksi, lähtöaineet taksaanivälituotteiden valmistamiseksi ja taksaanivälituotteet
SK281297B6 (sk)	2001-02-12	Spôsob prípravy beta-fenylizoserínu, jeho analógov a medziprodukt
FI119289B (fi)	2008-09-30	Menetelmä (4S, 5R)-1,3-oksatsolidin-5-karboksyylihapon valmistamiseksi ja menetelmä taksaanijohdannaisten valmistamiseksi näin saatua karboksyylihappoa käyttäen
AU2003219094B2 (en)	2008-06-26	A semi-synthetic process for the preparation of N debenzoylpaclitaxel
Monir et al.	2021	A mild approach to synthesise enantiopure glycine-derived 5-phenylthiomorpholinone
PL194032B1 (pl)	2007-04-30	Sposób wytwarzania półproduktów użytecznych w syntezie paklitakselu
WO2015036522A1 (en)	2015-03-19	Process for the preparation and isolation of (s)-3-amino-n-cyclopropyl-2,2-dialkoxyhexanamide and (s)-tert-butyl(1-(cyclopropylamino)-2,2-dialkoxy-1-oxohexan-3-yl)carbamate and use thereof for the preparation of telaprevir