LV10858B - Method for preparation of derivatives of taxane - Google Patents

Method for preparation of derivatives of taxane Download PDF

Info

Publication number: LV10858B
Authority: LV; Latvia
Prior art keywords: group; phenyl; acid; alkyl; general formula
Prior art date: 1992-10-05

Application number

LVP-93-1121A

Other languages

English (en)

Latvian (lv)

Other versions

LV10858A (lv

Inventor

Alain Commercon

Eric Didier

Elie Fouque

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

1993-10-04

Publication date

1996-06-20

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=9434120&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=LV10858(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1993-10-04 Application filed by Rhone Poulenc Rorer Sa filed Critical Rhone Poulenc Rorer Sa

1995-10-20 Publication of LV10858A publication Critical patent/LV10858A/xx

1996-06-20 Publication of LV10858B publication Critical patent/LV10858B/lv

Links

238000000034 method Methods 0.000 title claims abstract description 31
DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 title claims abstract description 6
238000002360 preparation method Methods 0.000 title claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 23
239000002253 acid Substances 0.000 claims abstract description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
230000032050 esterification Effects 0.000 claims abstract description 12
238000005886 esterification reaction Methods 0.000 claims abstract description 12
125000003118 aryl group Chemical group 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
238000010511 deprotection reaction Methods 0.000 claims abstract description 10
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
239000001257 hydrogen Substances 0.000 claims abstract description 9
150000001602 bicycloalkyls Chemical group 0.000 claims abstract description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 9
125000000217 alkyl group Chemical group 0.000 claims abstract 8
125000003545 alkoxy group Chemical group 0.000 claims abstract 5
125000003342 alkenyl group Chemical group 0.000 claims abstract 3
125000000304 alkynyl group Chemical group 0.000 claims abstract 3
125000000392 cycloalkenyl group Chemical group 0.000 claims abstract 3
125000000753 cycloalkyl group Chemical group 0.000 claims abstract 2
125000003107 substituted aryl group Chemical group 0.000 claims abstract 2
150000002148 esters Chemical class 0.000 claims description 36
-1 mercapto, formyl Chemical group 0.000 claims description 26
230000008569 process Effects 0.000 claims description 25
239000000203 mixture Substances 0.000 claims description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
239000003795 chemical substances by application Substances 0.000 claims description 16
239000002904 solvent Substances 0.000 claims description 16
229910052736 halogen Inorganic materials 0.000 claims description 14
150000002367 halogens Chemical class 0.000 claims description 14
150000002825 nitriles Chemical class 0.000 claims description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
150000008064 anhydrides Chemical class 0.000 claims description 11
239000002023 wood Substances 0.000 claims description 10
150000002170 ethers Chemical class 0.000 claims description 9
150000003927 aminopyridines Chemical group 0.000 claims description 8
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 8
229910052500 inorganic mineral Inorganic materials 0.000 claims description 8
239000011707 mineral Substances 0.000 claims description 8
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical group C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 7
150000002576 ketones Chemical class 0.000 claims description 7
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 6
239000011701 zinc Substances 0.000 claims description 6
229910052725 zinc Inorganic materials 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
239000011737 fluorine Substances 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
238000007327 hydrogenolysis reaction Methods 0.000 claims description 4
150000007524 organic acids Chemical class 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
125000004442 acylamino group Chemical group 0.000 claims description 3
125000005239 aroylamino group Chemical group 0.000 claims description 3
125000005333 aroyloxy group Chemical group 0.000 claims description 3
125000005110 aryl thio group Chemical group 0.000 claims description 3
125000004104 aryloxy group Chemical group 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
238000011065 in-situ storage Methods 0.000 claims description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 claims description 2
150000001298 alcohols Chemical class 0.000 claims description 2
150000001718 carbodiimides Chemical group 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 8
230000003213 activating effect Effects 0.000 claims 6
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical group CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims 4
239000003960 organic solvent Substances 0.000 claims 4
125000006239 protecting group Chemical group 0.000 claims 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 3
229930014667 baccatin III Natural products 0.000 claims 3
239000002609 medium Substances 0.000 claims 3
239000007800 oxidant agent Substances 0.000 claims 3
HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical group ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 claims 2
RGUKYNXWOWSRET-UHFFFAOYSA-N 4-pyrrolidin-1-ylpyridine Chemical compound C1CCCN1C1=CC=NC=C1 RGUKYNXWOWSRET-UHFFFAOYSA-N 0.000 claims 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 2
239000012736 aqueous medium Substances 0.000 claims 2
125000003710 aryl alkyl group Chemical group 0.000 claims 2
125000004429 atom Chemical group 0.000 claims 2
125000004432 carbon atom Chemical group C* 0.000 claims 2
229910052802 copper Inorganic materials 0.000 claims 2
239000010949 copper Substances 0.000 claims 2
125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 1
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical group OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 claims 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical group O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 claims 1
125000002252 acyl group Chemical group 0.000 claims 1
125000004423 acyloxy group Chemical group 0.000 claims 1
125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
125000004414 alkyl thio group Chemical group 0.000 claims 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
239000003054 catalyst Substances 0.000 claims 1
150000001875 compounds Chemical class 0.000 claims 1
125000004093 cyano group Chemical group *C#N 0.000 claims 1
125000005105 dialkylarylsilyl group Chemical group 0.000 claims 1
125000005117 dialkylcarbamoyl group Chemical group 0.000 claims 1
150000004820 halides Chemical class 0.000 claims 1
125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
XQSFXFQDJCDXDT-UHFFFAOYSA-N hydroxysilicon Chemical compound [Si]O XQSFXFQDJCDXDT-UHFFFAOYSA-N 0.000 claims 1
229910052740 iodine Inorganic materials 0.000 claims 1
239000011630 iodine Substances 0.000 claims 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
235000005985 organic acids Nutrition 0.000 claims 1
125000001477 organic nitrogen group Chemical group 0.000 claims 1
230000001590 oxidative effect Effects 0.000 claims 1
125000004076 pyridyl group Chemical group 0.000 claims 1
150000003510 tertiary aliphatic amines Chemical class 0.000 claims 1
125000004665 trialkylsilyl group Chemical group 0.000 claims 1
125000005106 triarylsilyl group Chemical group 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
230000008030 elimination Effects 0.000 abstract description 4
238000003379 elimination reaction Methods 0.000 abstract description 4
230000004224 protection Effects 0.000 abstract description 3
125000000623 heterocyclic group Chemical group 0.000 abstract description 2
YWLXLRUDGLRYDR-ZHPRIASZSA-N 5beta,20-epoxy-1,7beta,10beta,13alpha-tetrahydroxy-9-oxotax-11-ene-2alpha,4alpha-diyl 4-acetate 2-benzoate Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](O)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 YWLXLRUDGLRYDR-ZHPRIASZSA-N 0.000 abstract 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 76
150000003254 radicals Chemical class 0.000 description 49
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
238000001914 filtration Methods 0.000 description 21
238000001228 spectrum Methods 0.000 description 19
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
239000012071 phase Substances 0.000 description 17
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 15
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 14
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 14
239000011734 sodium Substances 0.000 description 14
229910052708 sodium Inorganic materials 0.000 description 14
238000010521 absorption reaction Methods 0.000 description 13
238000012512 characterization method Methods 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
230000000694 effects Effects 0.000 description 11
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
230000008878 coupling Effects 0.000 description 10
238000010168 coupling process Methods 0.000 description 10
238000005859 coupling reaction Methods 0.000 description 10
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 9
SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 8
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 8
238000004821 distillation Methods 0.000 description 8
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 8
239000002243 precursor Substances 0.000 description 8
238000010908 decantation Methods 0.000 description 7
238000006467 substitution reaction Methods 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
230000004913 activation Effects 0.000 description 6
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
125000001183 hydrocarbyl group Chemical group 0.000 description 6
WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical compound ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 description 6
238000010992 reflux Methods 0.000 description 6
230000003595 spectral effect Effects 0.000 description 6
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 5
238000009833 condensation Methods 0.000 description 5
230000005494 condensation Effects 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
235000010755 mineral Nutrition 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 5
239000000126 substance Substances 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 4
241000282994 Cervidae Species 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
230000009471 action Effects 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
230000002950 deficient Effects 0.000 description 4
239000007788 liquid Substances 0.000 description 4
230000001850 reproductive effect Effects 0.000 description 4
230000007958 sleep Effects 0.000 description 4
LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
229930012538 Paclitaxel Natural products 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
229940123237 Taxane Drugs 0.000 description 3
241001080024 Telles Species 0.000 description 3
238000013019 agitation Methods 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
FZRNJOXQNWVMIH-UHFFFAOYSA-N lithium;hydrate Chemical compound [Li].O FZRNJOXQNWVMIH-UHFFFAOYSA-N 0.000 description 3
230000005291 magnetic effect Effects 0.000 description 3
229960001592 paclitaxel Drugs 0.000 description 3
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
239000011591 potassium Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
230000002633 protecting effect Effects 0.000 description 3
239000000725 suspension Substances 0.000 description 3
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 3
239000008096 xylene Substances 0.000 description 3
150000003738 xylenes Chemical class 0.000 description 3
PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 2
HOJZAHQWDXAPDJ-UHFFFAOYSA-N 3-anilino-2-hydroxypropanoic acid Chemical compound OC(=O)C(O)CNC1=CC=CC=C1 HOJZAHQWDXAPDJ-UHFFFAOYSA-N 0.000 description 2
101150046236 CNR1 gene Proteins 0.000 description 2
229910052684 Cerium Inorganic materials 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
239000004593 Epoxy Substances 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
235000006679 Mentha X verticillata Nutrition 0.000 description 2
235000002899 Mentha suaveolens Nutrition 0.000 description 2
235000001636 Mentha x rotundifolia Nutrition 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-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
238000005481 NMR spectroscopy Methods 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
238000004364 calculation method Methods 0.000 description 2
GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 2
235000005911 diet Nutrition 0.000 description 2
230000000378 dietary effect Effects 0.000 description 2
229940082150 encore Drugs 0.000 description 2
239000000499 gel Substances 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
230000003834 intracellular effect Effects 0.000 description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropyl acetate Chemical compound CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
201000002266 mite infestation Diseases 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000013618 particulate matter Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
238000009877 rendering Methods 0.000 description 2
238000007127 saponification reaction Methods 0.000 description 2
239000012453 solvate Substances 0.000 description 2
125000003396 thiol group Chemical class [H]S* 0.000 description 2
TWNIXVUGXIBCDA-UHFFFAOYSA-N 1-hydroxy-2-piperidin-1-ylpiperidine Chemical compound N1(CCCCC1)C1N(CCCC1)O TWNIXVUGXIBCDA-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
101100322245 Caenorhabditis elegans des-2 gene Proteins 0.000 description 1
101100119767 Caenorhabditis elegans fat-4 gene Proteins 0.000 description 1
101100468762 Caenorhabditis elegans ric-3 gene Proteins 0.000 description 1
JYGLAHSAISAEAL-UHFFFAOYSA-N Diphenadione Chemical compound O=C1C2=CC=CC=C2C(=O)C1C(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 JYGLAHSAISAEAL-UHFFFAOYSA-N 0.000 description 1
241001644893 Entandrophragma utile Species 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
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 1
101100406879 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) par-2 gene Proteins 0.000 description 1
208000008589 Obesity Diseases 0.000 description 1
235000014548 Rubus moluccanus Nutrition 0.000 description 1
101100127888 Schizosaccharomyces pombe (strain 972 / ATCC 24843) les1 gene Proteins 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
239000012445 acidic reagent Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000013543 active substance Substances 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
DVARTQFDIMZBAA-UHFFFAOYSA-O ammonium nitrate Chemical compound [NH4+].[O-][N+]([O-])=O DVARTQFDIMZBAA-UHFFFAOYSA-O 0.000 description 1
230000003444 anaesthetic effect Effects 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
235000019568 aromas Nutrition 0.000 description 1
150000001719 carbohydrate derivatives Chemical class 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
230000002490 cerebral effect Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000000039 congener Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000009849 deactivation Effects 0.000 description 1
230000032798 delamination Effects 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
150000002085 enols Chemical class 0.000 description 1
238000005530 etching Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
235000013305 food Nutrition 0.000 description 1
230000002068 genetic effect Effects 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
239000011572 manganese Substances 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
150000007523 nucleic acids Chemical group 0.000 description 1
235000020824 obesity Nutrition 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
210000003463 organelle Anatomy 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000004321 preservation Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000000047 product Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
108090000623 proteins and genes Proteins 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
RONWGALEIBILOG-VMJVVOMYSA-N quinine sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 RONWGALEIBILOG-VMJVVOMYSA-N 0.000 description 1
230000009467 reduction Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000344 soap Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
230000007480 spreading Effects 0.000 description 1
238000003892 spreading Methods 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
229940063683 taxotere Drugs 0.000 description 1
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 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
- 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
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (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)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)

LVP-93-1121A 1992-10-05 1993-10-04 Method for preparation of derivatives of taxane LV10858B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR9211742A FR2696459B1 (fr)	1992-10-05	1992-10-05	Procédé de préparation de dérivés du taxane.

Publications (2)

Publication Number	Publication Date
LV10858A LV10858A (lv)	1995-10-20
LV10858B true LV10858B (en)	1996-06-20

Family

ID=9434120

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LVP-93-1121A LV10858B (en)	1992-10-05	1993-10-04	Method for preparation of derivatives of taxane

Country Status (31)

Country	Link
US (1)	US5637723A (zh)
EP (1)	EP0663907B1 (zh)
JP (1)	JP3014761B2 (zh)
KR (1)	KR100297197B1 (zh)
CN (1)	CN1048983C (zh)
AT (1)	ATE147735T1 (zh)
AU (1)	AU689081B2 (zh)
CA (1)	CA2146155C (zh)
CZ (1)	CZ283362B6 (zh)
DE (1)	DE69307527T2 (zh)
DK (1)	DK0663907T3 (zh)
EE (1)	EE03125B1 (zh)
ES (1)	ES2096329T3 (zh)
FI (1)	FI109791B (zh)
FR (1)	FR2696459B1 (zh)
GE (1)	GEP19981299B (zh)
GR (1)	GR3022285T3 (zh)
HU (1)	HU223775B1 (zh)
LT (1)	LT3439B (zh)
LV (1)	LV10858B (zh)
MX (1)	MX9305767A (zh)
NO (1)	NO310412B1 (zh)
NZ (1)	NZ256446A (zh)
PL (1)	PL179147B1 (zh)
RU (1)	RU2116302C1 (zh)
SG (1)	SG63619A1 (zh)
SK (1)	SK280624B6 (zh)
TW (1)	TW262471B (zh)
UA (1)	UA43835C2 (zh)
WO (1)	WO1994007878A1 (zh)
ZA (1)	ZA937319B (zh)

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US6794523B2 (en)	1991-09-23	2004-09-21	Florida State University	Taxanes having t-butoxycarbonyl substituted side-chains and pharmaceutical compositions containing them
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.
FR2698871B1 (fr)	1992-12-09	1995-02-24	Rhone Poulenc Rorer Sa	Nouveau taxoïdes, leur préparation et les compositions pharmaceutiques qui les contiennent.
IL107950A (en)	1992-12-15	2001-04-30	Upjohn Co	b 7, b 8 - Matano - Taxols, their preparation and pharmaceutical preparations against malignant tumors containing them
ES2145829T3 (es) *	1993-06-11	2000-07-16	Upjohn Co	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.
IL112412A (en) *	1994-01-28	2000-02-29	Upjohn Co	Delta 12,13-iso-taxol analogs and antineoplastic pharmaceutical compositions containing them
CA2170661A1 (en) *	1995-03-22	1996-09-23	John K. Thottathil	Novel methods for the preparation of taxanes using oaxzolidine intermediates
US5847170A (en) *	1995-03-27	1998-12-08	Rhone-Poulenc Rorer, S.A.	Taxoids, their preparation and pharmaceutical compositions containing them
US6372780B2 (en)	1995-03-27	2002-04-16	Aventis Pharma S.A.	Methods of treating cell lines expressing multidrug resistance P-glycoprotein
MA23823A1 (fr)	1995-03-27	1996-10-01	Aventis Pharma Sa	Nouveaux taxoides, leur preparation et les compositions qui les contiennent
EP0868422A1 (de) *	1996-09-24	1998-10-07	Marigen S.A.	Ultramikroemulsionen aus spontan dispergierbaren konzentraten mit antitumoral und antiviral wirksamen estern von baccatin-iii-verbindungen
FR2771092B1 (fr) *	1997-11-18	1999-12-17	Rhone Poulenc Rorer Sa	Procede de preparation de derives de la classe des taxoides
US6096250A (en) *	1998-03-06	2000-08-01	Caesar International, Inc.	Process for releasing a runner from an electronic device package on a laminate plate
US6156789A (en) *	1998-03-17	2000-12-05	Rhone-Poulenc Rorer S.A.	Method for treating abnormal cell proliferation in the brain
US6346543B1 (en)	1998-08-17	2002-02-12	Aventis Pharma S.A.	Use of a taxoid to treat abnormal cell proliferation in the brain
US6403634B1 (en)	1999-01-13	2002-06-11	Aventis Pharma S.A.	Use of taxoid derivatives
IT1308636B1 (it)	1999-03-02	2002-01-09	Indena Spa	Procedimento per la preparazione di tassani da 10-desacetilbaccatinaiii.
AU775373B2 (en)	1999-10-01	2004-07-29	Immunogen, Inc.	Compositions and methods for treating cancer using immunoconjugates and chemotherapeutic agents
WO2002066448A1 (en) *	2001-02-20	2002-08-29	Dabur India Limited	Method of preparation of paclitaxel (taxol) using 3-(alk-2-ynyloxy) carbonyl-5-oxazolidine carboxylic acid
DE01924282T1 (de) *	2001-03-23	2007-04-19	Scinopharm Taiwan, Ltd.	Verfahren zur herstellung von taxanderivaten
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
US6838569B2 (en)	2002-12-16	2005-01-04	Dabur India Limited	Process for preparation of paclitaxel trihydrate and docetaxel trihydrate
FR2882362B1 (fr) *	2005-02-23	2007-05-11	Seripharm	Procede de preparation du paclitaxel
AU2007309534B2 (en) *	2006-10-20	2012-08-16	Scinopharm Singapore Pte, Ltd.	Process for making crystalline anhydrous docetaxel
PL210984B1 (pl) *	2006-10-31	2012-03-30	Inst Farmaceutyczny	Sposób wytwarzania docetakselu
KR100847331B1 (ko) *	2006-12-14	2008-07-21	한미약품 주식회사	도세탁셀의 제조방법 및 이에 사용되는 중간체
KR100921036B1 (ko)	2006-12-18	2009-10-08	한미약품 주식회사	탁산유도체의 제조방법 및 이에 사용되는 중간체
KR101671537B1 (ko)	2008-08-11	2016-11-01	넥타르 테라퓨틱스	다분지형 중합체 알카노에이트 컨쥬게이트
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
WO2011134067A1 (en) *	2010-04-29	2011-11-03	6570763 Canada Inc.	Novel amino acid molecule and uses thereof
US20130331443A1 (en)	2010-12-22	2013-12-12	Nektar Therapeutics	Multi-arm polymeric prodrug conjugates of taxane-based compounds
US10894087B2 (en)	2010-12-22	2021-01-19	Nektar Therapeutics	Multi-arm polymeric prodrug conjugates of cabazitaxel-based compounds
WO2012088433A1 (en)	2010-12-22	2012-06-28	Nektar Therapeutics	Deuterated and/or fluorinated taxane derivatives
EP2760848B1 (en)	2011-09-26	2018-11-28	Fresenius Kabi Oncology Limited	Processes for the preparation of cabazitaxel involving c(7)-oh and c(13)-oh silylation or just c(7)-oh silylation
KR101379694B1 (ko)	2011-09-30	2014-03-31	주식회사 삼양바이오팜	탁산유도체의 제조방법
CN102382080B (zh) *	2011-12-15	2014-06-18	扬子江药业集团江苏海慈生物药业有限公司	一种多西他赛的制备方法
FR2986526A1 (fr) *	2012-02-03	2013-08-09	Sanofi Sa	Procede de preparation de derives du taxol et certains composes intermediaires
CN104650012A (zh) *	2013-11-22	2015-05-27	天士力控股集团有限公司	一种紫杉烷类化合物

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FR2601675B1 (fr)	1986-07-17	1988-09-23	Rhone Poulenc Sante	Derives du taxol, leur preparation et les compositions pharmaceutiques qui les contiennent
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
FR2687151B1 (fr) *	1992-02-07	1994-03-25	Rhone Poulenc Rorer Sa	Nouveaux derives de la baccatine iii et de la desacetyl-10 baccatine iii, leur preparation et les compositions pharmaceutiques qui les contiennent.
US5440056A (en) *	1992-04-17	1995-08-08	Abbott Laboratories	9-deoxotaxane compounds

1992
- 1992-10-05 FR FR9211742A patent/FR2696459B1/fr not_active Expired - Fee Related
1993
- 1993-04-10 UA UA95038242A patent/UA43835C2/uk unknown
- 1993-09-21 MX MX9305767A patent/MX9305767A/es unknown
- 1993-09-28 CN CN93118203A patent/CN1048983C/zh not_active Expired - Lifetime
- 1993-10-01 ZA ZA937319A patent/ZA937319B/xx unknown
- 1993-10-02 TW TW082108115A patent/TW262471B/zh not_active IP Right Cessation
- 1993-10-04 JP JP6508788A patent/JP3014761B2/ja not_active Expired - Lifetime
- 1993-10-04 CA CA002146155A patent/CA2146155C/fr not_active Expired - Lifetime
- 1993-10-04 DK DK93921983.8T patent/DK0663907T3/da active
- 1993-10-04 RU RU95110686A patent/RU2116302C1/ru active
- 1993-10-04 WO PCT/FR1993/000968 patent/WO1994007878A1/fr active IP Right Grant
- 1993-10-04 US US08/406,985 patent/US5637723A/en not_active Expired - Lifetime
- 1993-10-04 KR KR1019950701303A patent/KR100297197B1/ko not_active Expired - Lifetime
- 1993-10-04 NZ NZ256446A patent/NZ256446A/en not_active IP Right Cessation
- 1993-10-04 AU AU51151/93A patent/AU689081B2/en not_active Expired
- 1993-10-04 AT AT93921983T patent/ATE147735T1/de active
- 1993-10-04 GE GEAP19932473A patent/GEP19981299B/en unknown
- 1993-10-04 LV LVP-93-1121A patent/LV10858B/lv unknown
- 1993-10-04 SK SK435-95A patent/SK280624B6/sk not_active IP Right Cessation
- 1993-10-04 EP EP93921983A patent/EP0663907B1/fr not_active Expired - Lifetime
- 1993-10-04 DE DE69307527T patent/DE69307527T2/de not_active Expired - Lifetime
- 1993-10-04 PL PL93308306A patent/PL179147B1/pl unknown
- 1993-10-04 HU HU9500967A patent/HU223775B1/hu active IP Right Grant
- 1993-10-04 CZ CZ95842A patent/CZ283362B6/cs not_active IP Right Cessation
- 1993-10-04 LT LTIP1396A patent/LT3439B/lt not_active IP Right Cessation
- 1993-10-04 ES ES93921983T patent/ES2096329T3/es not_active Expired - Lifetime
- 1993-10-04 SG SG1996007545A patent/SG63619A1/en unknown
1994
- 1994-11-18 EE EE9400361A patent/EE03125B1/xx unknown
1995
- 1995-03-29 NO NO19951202A patent/NO310412B1/no not_active IP Right Cessation
- 1995-04-04 FI FI951591A patent/FI109791B/fi not_active IP Right Cessation
1997
- 1997-01-16 GR GR960402651T patent/GR3022285T3/el unknown

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Publication number	Publication date
CA2146155C (fr)	2003-03-11
PL179147B1 (pl)	2000-07-31
JP3014761B2 (ja)	2000-02-28
SG63619A1 (en)	1999-03-30
NZ256446A (en)	1996-06-25
KR950703547A (ko)	1995-09-20
FI951591L (fi)	1995-04-04
ATE147735T1 (de)	1997-02-15
FI951591A0 (fi)	1995-04-04
LT3439B (en)	1995-10-25
EP0663907B1 (fr)	1997-01-15
NO951202D0 (no)	1995-03-29
RU2116302C1 (ru)	1998-07-27
FI109791B (fi)	2002-10-15
HU9500967D0 (en)	1995-06-28
US5637723A (en)	1997-06-10
HUT72612A (en)	1996-05-28
MX9305767A (es)	1994-05-31
TW262471B (zh)	1995-11-11
EP0663907A1 (fr)	1995-07-26
SK280624B6 (sk)	2000-05-16
PL308306A1 (en)	1995-07-24
HU223775B1 (hu)	2005-01-28
FR2696459A1 (fr)	1994-04-08
WO1994007878A1 (fr)	1994-04-14
DE69307527D1 (de)	1997-02-27
CN1048983C (zh)	2000-02-02
JPH08501789A (ja)	1996-02-27
NO951202L (no)	1995-03-29
CN1087905A (zh)	1994-06-15
AU5115193A (en)	1994-04-26
AU689081B2 (en)	1998-03-26
LV10858A (lv)	1995-10-20
ES2096329T3 (es)	1997-03-01
UA43835C2 (uk)	2002-01-15
RU95110686A (ru)	1996-12-27
CZ283362B6 (cs)	1998-03-18
DE69307527T2 (de)	1997-05-22
SK43595A3 (en)	1995-08-09
DK0663907T3 (da)	1997-02-03
KR100297197B1 (ko)	2001-11-26
LTIP1396A (en)	1995-01-31
ZA937319B (en)	1994-04-22
GR3022285T3 (en)	1997-04-30
CA2146155A1 (fr)	1994-04-14
EE03125B1 (et)	1998-10-15
CZ84295A3 (en)	1995-09-13
NO310412B1 (no)	2001-07-02
GEP19981299B (en)	1998-05-01
FR2696459B1 (fr)	1994-11-25

Publication	Publication Date	Title
LV10858B (en)	1996-06-20	Method for preparation of derivatives of taxane
EP0663908B1 (fr)	1997-02-12	Procede de preparation de derives du taxane
EP0663906B1 (fr)	1996-12-11	Procede de preparation de derives du taxane
EP0253738B1 (fr)	1990-01-31	Dérivés du taxol, leur préparation et les compositions pharmaceutiques qui les contiennent
EP0663905B1 (fr)	1997-01-15	Nouveau procede d'esterification de la baccatine iii et de la desacetyl-10 baccatine iii
EP0253739B1 (fr)	1989-10-11	Procédé de préparation du taxol et du désacétyl-10 taxol
EP0593641B1 (fr)	1995-12-27	Procede de preparation de derives de la baccatine iii et de la desacetyl-10 baccatine iii
CA2013324C (fr)	2001-08-21	Pteridin-4 (3h)-ones, procedes de preparation et medicaments les contenant
WO1992009589A1 (fr)	1992-06-11	Procede de preparation de derives du taxane, nouveaux derives obtenus et compositions pharmaceutiques qui les contiennent
EP0666857B1 (fr)	1999-05-19	Procede de preparation de derives du taxane
EP0669916B1 (fr)	1997-01-22	Nouveau procede de preparation de derives du taxane, nouveaux derives ainsi obtenus et les compositions qui les contiennent
EP0630365B1 (fr)	1997-10-22	Procede de preparation de la beta-phenylisoserine et de ses analogues
FR2706457A1 (fr)	1994-12-23	Procédé de préparation d'un acide oxazolidinecarboxylique utile pour préparer des taxoïdes thérapeutiquement actifs.
FR2669631A1 (fr)	1992-05-29	Nouveaux derives de l'oxazolidine, leur preparation et leur emploi.
US5648505A (en)	1997-07-15	Method for the preparation of a novel C-ring precursor for taxoids and novel intermediates
FR2698361A1 (fr)	1994-05-27	Procédé de préparation d'un acide oxazolidine-1,3 carboxylique-5.
EP0454587A1 (fr)	1991-10-30	Nouveaux dérivés hétérocycliques : 2-styryl 4H-1-benzopyrane-4-ones, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent
WO2004018481A2 (fr)	2004-03-04	Derives du gossypol, leurs procedes d'obtention, et leurs utilisations
EP0747372A1 (en)	1996-12-11	Taxane derivatives from 14-beta-hydroxy-10 deacetybaccatin III
WO1994012485A1 (fr)	1994-06-09	Nouveaux taxoides, leur preparation et les compositions pharmaceutiques qui les contiennent