OA10855A - Nouveaux taxoïdes leur préparation et les compositions pharmaceutiques qui les contiennent - Google Patents

Nouveaux taxoïdes leur préparation et les compositions pharmaceutiques qui les contiennent Download PDF

Info

Publication number: OA10855A
Authority: OA; OAPI
Prior art keywords: carbon atoms; radical; general formula; radicals; atoms
Prior art date: 1996-03-06

Application number

OA9800161A

Other languages

English (en)

French (fr)

Inventor

Herve Bouchard

Jean-Dominique Bourzat

Alain Commercon

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.)

1996-03-06

Filing date

1998-09-04

Publication date

2003-02-05

1998-09-04 Application filed by Rhone Poulenc Rorer Sa filed Critical Rhone Poulenc Rorer Sa

2003-02-05 Publication of OA10855A publication Critical patent/OA10855A/fr

Links

239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 6
238000002360 preparation method Methods 0.000 title claims abstract description 6
-1 alkenoyloxy Chemical group 0.000 claims abstract description 151
125000000217 alkyl group Chemical group 0.000 claims abstract description 44
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 40
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
125000003342 alkenyl group Chemical group 0.000 claims abstract description 13
125000003545 alkoxy group Chemical group 0.000 claims abstract description 13
125000000304 alkynyl group Chemical group 0.000 claims abstract description 11
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 11
LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical class O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 claims abstract description 8
125000005133 alkynyloxy group Chemical group 0.000 claims abstract description 6
150000001875 compounds Chemical class 0.000 claims abstract description 6
125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 6
125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 6
125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 5
125000004465 cycloalkenyloxy group Chemical group 0.000 claims abstract description 4
125000004423 acyloxy group Chemical group 0.000 claims abstract description 3
150000001602 bicycloalkyls Chemical group 0.000 claims abstract description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 162
150000003254 radicals Chemical class 0.000 claims description 65
125000006239 protecting group Chemical group 0.000 claims description 23
125000004429 atom Chemical group 0.000 claims description 21
125000005843 halogen group Chemical group 0.000 claims description 21
239000000203 mixture Substances 0.000 claims description 19
239000003960 organic solvent Substances 0.000 claims description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 15
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 14
229910052799 carbon Inorganic materials 0.000 claims description 13
238000000034 method Methods 0.000 claims description 13
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
150000002148 esters Chemical class 0.000 claims description 11
229910052757 nitrogen Inorganic materials 0.000 claims description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
125000004663 dialkyl amino group Chemical group 0.000 claims description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
239000003795 chemical substances by application Substances 0.000 claims description 9
229910052760 oxygen Inorganic materials 0.000 claims description 9
239000001301 oxygen Substances 0.000 claims description 9
229920006395 saturated elastomer Polymers 0.000 claims description 9
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 8
230000032050 esterification Effects 0.000 claims description 8
238000005886 esterification reaction Methods 0.000 claims description 8
TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical group [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
230000008569 process Effects 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
125000004414 alkyl thio group Chemical group 0.000 claims description 7
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 7
125000003118 aryl group Chemical group 0.000 claims description 7
150000005840 aryl radicals Chemical class 0.000 claims description 7
125000005842 heteroatom Chemical group 0.000 claims description 7
125000000623 heterocyclic group Chemical group 0.000 claims description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims description 6
125000003282 alkyl amino group Chemical group 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
125000005117 dialkylcarbamoyl group Chemical group 0.000 claims description 6
150000002170 ethers Chemical class 0.000 claims description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
239000011593 sulfur Chemical group 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
125000004442 acylamino group Chemical group 0.000 claims description 5
239000002671 adjuvant Substances 0.000 claims description 5
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 5
150000002825 nitriles Chemical class 0.000 claims description 5
150000007524 organic acids Chemical class 0.000 claims description 5
125000005118 N-alkylcarbamoyl group Chemical group 0.000 claims description 4
230000003213 activating effect Effects 0.000 claims description 4
150000001298 alcohols Chemical class 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 4
125000003710 aryl alkyl group Chemical group 0.000 claims description 4
239000002585 base Substances 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
150000007522 mineralic acids Chemical class 0.000 claims description 4
125000004430 oxygen atom Chemical group O* 0.000 claims description 4
OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 claims description 3
IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical group C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 0.000 claims description 3
150000008064 anhydrides Chemical class 0.000 claims description 3
125000005239 aroylamino group Chemical group 0.000 claims description 3
125000005129 aryl carbonyl 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
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
150000001721 carbon Chemical group 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
125000004434 sulfur atom Chemical group 0.000 claims description 3
QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 claims description 3
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims description 2
229910000102 alkali metal hydride Inorganic materials 0.000 claims description 2
150000008046 alkali metal hydrides Chemical class 0.000 claims description 2
125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 2
125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 2
125000001589 carboacyl group Chemical group 0.000 claims description 2
230000003197 catalytic effect Effects 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
150000004820 halides Chemical class 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
229930195733 hydrocarbon Natural products 0.000 claims description 2
238000011065 in-situ storage Methods 0.000 claims description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
229910052739 hydrogen Inorganic materials 0.000 claims 3
239000001257 hydrogen Substances 0.000 claims 3
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
238000009833 condensation Methods 0.000 claims 1
230000005494 condensation Effects 0.000 claims 1
125000002541 furyl group Chemical group 0.000 claims 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
230000000259 anti-tumor effect Effects 0.000 abstract description 3
230000000118 anti-neoplastic effect Effects 0.000 abstract 1
125000005199 aryl carbonyloxy group Chemical group 0.000 abstract 1
125000001624 naphthyl group Chemical group 0.000 abstract 1
239000000047 product Substances 0.000 description 62
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 21
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
239000012074 organic phase Substances 0.000 description 14
239000000243 solution Substances 0.000 description 14
239000011521 glass Substances 0.000 description 12
238000003756 stirring Methods 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
230000009471 action Effects 0.000 description 9
238000004587 chromatography analysis Methods 0.000 description 9
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
239000003480 eluent Substances 0.000 description 8
239000000377 silicon dioxide Substances 0.000 description 8
WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 7
239000008346 aqueous phase Substances 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 7
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 7
239000012153 distilled water Substances 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
239000000499 gel Substances 0.000 description 7
229910052943 magnesium sulfate Inorganic materials 0.000 description 7
235000019341 magnesium sulphate Nutrition 0.000 description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
238000011282 treatment Methods 0.000 description 7
206010028980 Neoplasm Diseases 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
125000004356 hydroxy functional group Chemical group O* 0.000 description 6
239000012429 reaction media Substances 0.000 description 6
230000002159 abnormal effect Effects 0.000 description 5
238000010908 decantation Methods 0.000 description 5
230000001575 pathological effect Effects 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 4
239000004593 Epoxy Substances 0.000 description 4
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
229910052786 argon Inorganic materials 0.000 description 4
230000004663 cell proliferation Effects 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
229910052731 fluorine Inorganic materials 0.000 description 4
239000011737 fluorine Substances 0.000 description 4
LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
230000001225 therapeutic effect Effects 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000007900 aqueous suspension Substances 0.000 description 3
239000012300 argon atmosphere Substances 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
210000004027 cell Anatomy 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
230000004807 localization Effects 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
239000011707 mineral Substances 0.000 description 3
238000007911 parenteral administration Methods 0.000 description 3
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239000000126 substance Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
238000002560 therapeutic procedure Methods 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
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 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical class [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
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DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
108090000704 Tubulin Proteins 0.000 description 2
102000004243 Tubulin Human genes 0.000 description 2
RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 description 2
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210000004556 brain Anatomy 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
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150000002576 ketones Chemical class 0.000 description 2
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NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
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239000003607 modifier Substances 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
210000000056 organ Anatomy 0.000 description 2
125000000160 oxazolidinyl group Chemical group 0.000 description 2
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239000002504 physiological saline solution Substances 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
230000009467 reduction Effects 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
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229940063683 taxotere Drugs 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
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 2
NTJBWZHVSJNKAD-UHFFFAOYSA-N triethylazanium;fluoride Chemical compound [F-].CC[NH+](CC)CC NTJBWZHVSJNKAD-UHFFFAOYSA-N 0.000 description 2
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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 1
RCINICONZNJXQF-XAZOAEDWSA-N taxol® Chemical compound O([C@@H]1[C@@]2(CC(C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3(C21)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-XAZOAEDWSA-N 0.000 description 1
229960001278 teniposide Drugs 0.000 description 1
NRUKOCRGYNPUPR-QBPJDGROSA-N teniposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@@H](OC[C@H]4O3)C=3SC=CC=3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NRUKOCRGYNPUPR-QBPJDGROSA-N 0.000 description 1
125000006633 tert-butoxycarbonylamino group Chemical group 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
229960001712 testosterone propionate Drugs 0.000 description 1
230000004797 therapeutic response Effects 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
210000001685 thyroid gland Anatomy 0.000 description 1
MNRILEROXIRVNJ-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=NC=N[C]21 MNRILEROXIRVNJ-UHFFFAOYSA-N 0.000 description 1
229960003087 tioguanine Drugs 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
150000004654 triazenes Chemical class 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
229960003048 vinblastine Drugs 0.000 description 1
JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
229960004528 vincristine Drugs 0.000 description 1
OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/14—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/337—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having four-membered rings, e.g. taxol
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/06—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings
- 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
- C07D413/12—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 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Epoxy Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicines Containing Plant Substances (AREA)
Plural Heterocyclic Compounds (AREA)

OA9800161A 1996-03-06 1998-09-04 Nouveaux taxoïdes leur préparation et les compositions pharmaceutiques qui les contiennent OA10855A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR9602804A FR2745814B1 (fr)	1996-03-06	1996-03-06	Nouveaux taxoides, leur preparation et les compositions pharmaceutiques qui les contiennent

Publications (1)

Publication Number	Publication Date
OA10855A true OA10855A (fr)	2003-02-05

Family

ID=9489910

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA9800161A OA10855A (fr)	1996-03-06	1998-09-04	Nouveaux taxoïdes leur préparation et les compositions pharmaceutiques qui les contiennent

Country Status (34)

Country	Link
US (1)	US6160135A (de)
EP (1)	EP0885208B1 (de)
JP (1)	JP2000506158A (de)
KR (1)	KR19990087398A (de)
CN (1)	CN1210525A (de)
AP (1)	AP1023A (de)
AT (1)	ATE204266T1 (de)
AU (1)	AU715228B2 (de)
BG (1)	BG63693B1 (de)
BR (1)	BR9707887A (de)
CA (1)	CA2248195A1 (de)
CZ (1)	CZ283498A3 (de)
DE (1)	DE69706146T2 (de)
DK (1)	DK0885208T3 (de)
EA (1)	EA001516B1 (de)
EE (1)	EE03611B1 (de)
ES (1)	ES2161446T3 (de)
FR (1)	FR2745814B1 (de)
GE (1)	GEP20012517B (de)
GR (1)	GR3036410T3 (de)
HU (1)	HUP9902425A3 (de)
IL (1)	IL125998A (de)
IS (1)	IS4809A (de)
NO (1)	NO983472D0 (de)
NZ (1)	NZ331040A (de)
OA (1)	OA10855A (de)
PL (1)	PL328691A1 (de)
PT (1)	PT885208E (de)
SK (1)	SK121598A3 (de)
TR (1)	TR199801732T2 (de)
TW (1)	TW474928B (de)
WO (1)	WO1997032869A1 (de)
YU (1)	YU38398A (de)
ZA (1)	ZA971746B (de)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5973160A (en)	1992-12-23	1999-10-26	Poss; Michael A.	Methods for the preparation of novel sidechain-bearing taxanes
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
EP1044971A4 (de) *	1997-12-19	2001-11-07	Yakult Honsha Kk	Taxan-derivate
EP1020188A1 (de) *	1999-01-13	2000-07-19	Aventis Pharma S.A.	Neue Verwendung von Taxoid-Derivaten
CO5280224A1 (es) *	2000-02-02	2003-05-30	Univ Florida State Res Found	Taxanos sustituidos con ester en c7, utiles como agentes antitumorales y composiciones farmaceuticas que los contienen
PL350028A1 (en) *	2000-02-02	2002-10-21	Univ Florida State Res Found	C10 carbonate substituted taxanes as antitumor agents
JP2004525860A (ja)	2000-09-22	2004-08-26	ブリストル−マイヤーズスクイブカンパニー	併用化学療法剤の毒性を低下させる方法
FR2859996B1 (fr) *	2003-09-19	2006-02-03	Aventis Pharma Sa	Solvat acetonique du dimethoxy docetaxel et son procede de preparation
CN1960721A (zh)	2004-03-05	2007-05-09	佛罗里达州立大学研究基金有限公司	C7乳酰氧基取代的紫杉烷类
CN101835769A (zh) *	2007-08-22	2010-09-15	6570763加拿大有限公司	将9-二氢-13-乙酰基浆果赤霉素ⅲ转化为多烯紫杉醇或太平洋紫杉醇的方法
FR2926551A1 (fr) *	2008-01-17	2009-07-24	Aventis Pharma Sa	Formes cristallines du dimethoxy docetaxel et leurs procedes de preparation
AU2010310986A1 (en)	2009-10-29	2012-06-14	Aventis Pharma S.A.	Novel antitumoral use of cabazitaxel
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

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5136060A (en) *	1989-11-14	1992-08-04	Florida State University	Method for preparation of taxol using an oxazinone
KR930702323A (ko) *	1991-07-17	1993-09-08	하지메 나까가와	항종양 활성을 가진 화합물(nsc-lsc1) 및 그의 제조방법
CA2100808A1 (en) *	1992-10-01	1994-04-02	Vittorio Farina	Deoxy paclitaxels
DK1227093T3 (da) *	1993-03-22	2005-08-29	Univ Florida State	Beta-lactamer, der kan anvendes til fremstilling af taxaner med en furyl- eller thienylsubstitueret sidekæde
FR2711369B1 (fr) *	1993-10-20	1995-11-17	Rhone Poulenc Rorer Sa	Nouveaux taxoïdes, leur préparation et les compositions qui les contiennent.
AU684218B2 (en) *	1994-07-26	1997-12-04	Indena S.P.A.	Semi-synthetic taxanes with anti-tumoural activity
US6201140B1 (en) *	1994-07-28	2001-03-13	Bristol-Myers Squibb Company	7-0-ethers of taxane derivatives

1996
- 1996-03-06 FR FR9602804A patent/FR2745814B1/fr not_active Expired - Fee Related
1997
- 1997-02-26 TW TW086102360A patent/TW474928B/zh active
- 1997-02-27 ZA ZA9701746A patent/ZA971746B/xx unknown
- 1997-03-05 PL PL97328691A patent/PL328691A1/xx unknown
- 1997-03-05 TR TR1998/01732T patent/TR199801732T2/xx unknown
- 1997-03-05 BR BR9707887-5A patent/BR9707887A/pt unknown
- 1997-03-05 DE DE69706146T patent/DE69706146T2/de not_active Expired - Fee Related
- 1997-03-05 CA CA002248195A patent/CA2248195A1/fr not_active Abandoned
- 1997-03-05 NZ NZ331040A patent/NZ331040A/en unknown
- 1997-03-05 IL IL12599897A patent/IL125998A/en not_active IP Right Cessation
- 1997-03-05 ES ES97908304T patent/ES2161446T3/es not_active Expired - Lifetime
- 1997-03-05 AT AT97908304T patent/ATE204266T1/de not_active IP Right Cessation
- 1997-03-05 GE GEAP19974503A patent/GEP20012517B/en unknown
- 1997-03-05 WO PCT/FR1997/000386 patent/WO1997032869A1/fr not_active Ceased
- 1997-03-05 EP EP97908304A patent/EP0885208B1/de not_active Expired - Lifetime
- 1997-03-05 AU AU20302/97A patent/AU715228B2/en not_active Ceased
- 1997-03-05 AP APAP/P/1998/001335A patent/AP1023A/en active
- 1997-03-05 CZ CZ982834A patent/CZ283498A3/cs unknown
- 1997-03-05 HU HU9902425A patent/HUP9902425A3/hu unknown
- 1997-03-05 JP JP9531523A patent/JP2000506158A/ja active Pending
- 1997-03-05 KR KR1019980706814A patent/KR19990087398A/ko not_active Withdrawn
- 1997-03-05 PT PT97908304T patent/PT885208E/pt unknown
- 1997-03-05 CN CN97192042A patent/CN1210525A/zh active Pending
- 1997-03-05 EA EA199800795A patent/EA001516B1/ru not_active IP Right Cessation
- 1997-03-05 SK SK1215-98A patent/SK121598A3/sk unknown
- 1997-03-05 EE EE9800264A patent/EE03611B1/xx not_active IP Right Cessation
- 1997-03-05 DK DK97908304T patent/DK0885208T3/da active
- 1997-03-05 US US09/117,659 patent/US6160135A/en not_active Expired - Fee Related
1998
- 1998-07-24 IS IS4809A patent/IS4809A/is unknown
- 1998-07-28 NO NO983472A patent/NO983472D0/no not_active Application Discontinuation
- 1998-09-03 YU YU38398A patent/YU38398A/sh unknown
- 1998-09-04 BG BG102753A patent/BG63693B1/bg unknown
- 1998-09-04 OA OA9800161A patent/OA10855A/fr unknown
2001
- 2001-08-20 GR GR20010400596T patent/GR3036410T3/el not_active IP Right Cessation

Also Published As

Publication number	Publication date
ATE204266T1 (de)	2001-09-15
AP1023A (en)	2001-11-16
NO983472L (no)	1998-07-28
DK0885208T3 (da)	2001-10-15
IS4809A (is)	1998-07-24
EE9800264A (et)	1999-02-15
GR3036410T3 (en)	2001-11-30
CN1210525A (zh)	1999-03-10
DE69706146D1 (de)	2001-09-20
CZ283498A3 (cs)	1999-01-13
EA001516B1 (ru)	2001-04-23
YU38398A (sh)	1999-07-28
DE69706146T2 (de)	2002-05-02
FR2745814A1 (fr)	1997-09-12
US6160135A (en)	2000-12-12
BG102753A (en)	1999-09-30
KR19990087398A (ko)	1999-12-27
EP0885208A1 (de)	1998-12-23
NZ331040A (en)	2000-02-28
EP0885208B1 (de)	2001-08-16
SK121598A3 (en)	1999-01-11
AU715228B2 (en)	2000-01-20
IL125998A0 (en)	1999-04-11
HUP9902425A3 (en)	2001-08-28
NO983472D0 (no)	1998-07-28
AP9801335A0 (en)	1998-09-30
JP2000506158A (ja)	2000-05-23
FR2745814B1 (fr)	1998-04-03
HUP9902425A2 (hu)	2001-04-28
TR199801732T2 (xx)	1998-12-21
PT885208E (pt)	2001-11-30
EA199800795A1 (ru)	1999-02-25
PL328691A1 (en)	1999-02-15
IL125998A (en)	2002-02-10
EE03611B1 (et)	2002-02-15
ES2161446T3 (es)	2001-12-01
GEP20012517B (en)	2001-08-27
WO1997032869A1 (fr)	1997-09-12
ZA971746B (en)	1997-09-16
BR9707887A (pt)	1999-09-21
TW474928B (en)	2002-02-01
BG63693B1 (bg)	2002-09-30
AU2030297A (en)	1997-09-22
CA2248195A1 (fr)	1997-09-12

Publication	Publication Date	Title
CA2214321C (fr)	2008-01-22	Nouveaux taxoides, leur preparation et les compositions pharmaceutiques qui les contiennent
CA2238884C (fr)	2007-02-06	Nouveaux taxoides, leur preparation et les compositions pharmaceutiques qui les contiennent
EP0820448B1 (de)	2000-05-31	Taxal derivate, deren herstellung und diese enthaltende pharmazeutische zusammenstellungen
EP0885208B1 (de)	2001-08-16	Taxoide, ihre herstellung und diese enthaltende pharmazeutische zusammensetzungen
EP0821680B1 (de)	2000-08-30	Taxol derivate,deren herstellung und diese enthaltende pharmazeutische zusammenstellungen
EP0788492B1 (de)	1999-03-31	Texol-derivate, deren herstellung und diese enthaltende pharmazeutische zusammenstellungen
CA2190659C (fr)	2007-05-29	Taxoides, leur preparation et les compositions pharmaceutiques qui les contiennent
EP0764154A1 (de)	1997-03-26	Taxal derivate, deren herstellung und diese enthaltende pharmazeutische zusammenstellungen
EP0874838B1 (de)	2001-08-16	Neue taxoide, herstellung und pharmazeutische zusammensetzungen diese enthaltend
FR2732341A1 (fr)	1996-10-04	Nouveaux taxoides, leur preparation et les compositions pharmaceutiques qui les contiennent
CA2214320C (fr)	2007-02-06	Nouveaux taxoides, leur preparation et les compositions pharmaceutiques qui les contiennent
FR2732340A1 (fr)	1996-10-04	Nouveaux taxoides, leur preparation et les compositions pharmaceutiques qui les contiennent
EP0764156A1 (de)	1997-03-26	Taxol derivate, deren herstellung und diese enthaltende pharmazeutische zusammenstellungen
WO1994012485A1 (fr)	1994-06-09	Nouveaux taxoides, leur preparation et les compositions pharmaceutiques qui les contiennent