AP784A - Novel taxoids, preparation thereof and pharmaceutiacl compositions containing same. - Google Patents

Novel taxoids, preparation thereof and pharmaceutiacl compositions containing same. Download PDF

Info

Publication number: AP784A
Authority: AP; ARIPO
Prior art keywords: radical; carbon atoms; radicals; atoms; alkyl
Prior art date: 1995-04-03

Application number

APAP/P/1997/001094A

Other languages

English (en)

Other versions

AP9701094A0 (en

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.)

1995-04-03

Filing date

1996-04-01

Publication date

1999-11-22

1996-04-01 Application filed by Rhone Poulenc Rorer Sa filed Critical Rhone Poulenc Rorer Sa

1997-10-31 Publication of AP9701094A0 publication Critical patent/AP9701094A0/xx

1999-11-22 Application granted granted Critical

1999-11-22 Publication of AP784A publication Critical patent/AP784A/en

Links

239000000203 mixture Substances 0.000 title description 18
238000002360 preparation method Methods 0.000 title description 3
125000000217 alkyl group Chemical group 0.000 claims abstract description 55
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 40
125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
125000000304 alkynyl group Chemical group 0.000 claims abstract description 6
-1 alkyl radical Chemical class 0.000 claims description 227
125000004432 carbon atom Chemical group C* 0.000 claims description 142
150000003254 radicals Chemical class 0.000 claims description 64
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 46
125000005843 halogen group Chemical group 0.000 claims description 24
239000002253 acid Substances 0.000 claims description 23
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 22
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
150000008064 anhydrides Chemical class 0.000 claims description 17
229910052757 nitrogen Inorganic materials 0.000 claims description 17
125000004429 atom Chemical group 0.000 claims description 16
125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
125000006239 protecting group Chemical group 0.000 claims description 15
230000032050 esterification Effects 0.000 claims description 14
238000005886 esterification reaction Methods 0.000 claims description 14
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 13
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
238000000034 method Methods 0.000 claims description 13
239000003960 organic solvent Substances 0.000 claims description 13
229910052760 oxygen Inorganic materials 0.000 claims description 13
239000001301 oxygen Substances 0.000 claims description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
125000005842 heteroatom Chemical group 0.000 claims description 12
125000003118 aryl group Chemical group 0.000 claims description 11
239000005864 Sulphur Substances 0.000 claims description 10
150000002148 esters Chemical class 0.000 claims description 10
229920006395 saturated elastomer Polymers 0.000 claims description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
239000000460 chlorine Substances 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 9
125000004093 cyano group Chemical group *C#N 0.000 claims description 9
229910052731 fluorine Inorganic materials 0.000 claims description 9
239000011737 fluorine Substances 0.000 claims description 9
150000004820 halides Chemical class 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 8
150000005840 aryl radicals Chemical class 0.000 claims description 8
239000003795 chemical substances by application Substances 0.000 claims description 8
125000004663 dialkyl amino group Chemical group 0.000 claims description 8
LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical group O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 claims description 8
230000008569 process Effects 0.000 claims description 8
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 7
125000004442 acylamino group Chemical group 0.000 claims description 7
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 7
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 6
150000007522 mineralic acids Chemical class 0.000 claims description 6
150000007524 organic acids Chemical class 0.000 claims description 6
KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical compound O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 claims description 5
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 5
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 5
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 5
125000003710 aryl alkyl group Chemical group 0.000 claims description 5
125000004104 aryloxy group Chemical group 0.000 claims description 5
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
125000005117 dialkylcarbamoyl group Chemical group 0.000 claims description 5
150000002170 ethers Chemical class 0.000 claims description 5
150000002825 nitriles Chemical class 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
230000003213 activating effect Effects 0.000 claims description 4
125000003282 alkyl amino group Chemical group 0.000 claims description 4
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 claims description 4
IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical compound C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 0.000 claims description 3
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
150000001298 alcohols Chemical class 0.000 claims description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 3
125000005239 aroylamino group Chemical group 0.000 claims description 3
125000005110 aryl thio 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
229910052799 carbon Inorganic materials 0.000 claims description 3
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 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
125000000160 oxazolidinyl group 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
OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 claims description 2
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims description 2
150000004200 baccatin III derivatives Chemical class 0.000 claims description 2
125000004369 butenyl group Chemical group C(=CCC)* 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
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
125000002541 furyl group Chemical group 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
239000008194 pharmaceutical composition Substances 0.000 claims description 2
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
125000006633 tert-butoxycarbonylamino group Chemical group 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 3
229930195733 hydrocarbon Natural products 0.000 claims 1
150000002430 hydrocarbons Chemical class 0.000 claims 1
230000001681 protective effect Effects 0.000 claims 1
230000000694 effects Effects 0.000 abstract description 3
125000000753 cycloalkyl group Chemical group 0.000 abstract 2
125000006615 aromatic heterocyclic group Chemical group 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
150000001602 bicycloalkyls Chemical group 0.000 abstract 1
125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
239000000047 product Substances 0.000 description 66
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 44
239000006260 foam Substances 0.000 description 43
239000000243 solution Substances 0.000 description 23
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
230000002829 reductive effect Effects 0.000 description 20
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 19
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
230000008878 coupling Effects 0.000 description 17
238000010168 coupling process Methods 0.000 description 17
238000005859 coupling reaction Methods 0.000 description 17
239000000126 substance Substances 0.000 description 17
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
230000003287 optical effect Effects 0.000 description 15
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 15
239000011521 glass Substances 0.000 description 13
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 13
238000003756 stirring Methods 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
239000012153 distilled water Substances 0.000 description 10
ZVAFCKLQJCZGAP-WDEREUQCSA-N (2r,3s)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H]([C@@H](O)C(O)=O)C1=CC=CC=C1 ZVAFCKLQJCZGAP-WDEREUQCSA-N 0.000 description 9
MSVWUXLRSKRKFZ-IPMKNSEASA-N (2r,4s,5r)-2-(4-methoxyphenyl)-3-[(2-methylpropan-2-yl)oxycarbonyl]-4-phenyl-1,3-oxazolidine-5-carboxylic acid Chemical compound C1=CC(OC)=CC=C1[C@@H]1N(C(=O)OC(C)(C)C)[C@@H](C=2C=CC=CC=2)[C@H](C(O)=O)O1 MSVWUXLRSKRKFZ-IPMKNSEASA-N 0.000 description 9
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 9
206010028980 Neoplasm Diseases 0.000 description 9
238000004587 chromatography analysis Methods 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
238000011282 treatment Methods 0.000 description 9
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 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
229910052943 magnesium sulfate Inorganic materials 0.000 description 8
235000019341 magnesium sulphate Nutrition 0.000 description 8
239000000377 silicon dioxide Substances 0.000 description 8
239000003480 eluent Substances 0.000 description 7
OVMSOCFBDVBLFW-VHLOTGQHSA-N 5beta,20-epoxy-1,7beta,13alpha-trihydroxy-9-oxotax-11-ene-2alpha,4alpha,10beta-triyl 4,10-diacetate 2-benzoate Chemical compound O([C@@H]1[C@@]2(C[C@H](O)C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)O)C(=O)C1=CC=CC=C1 OVMSOCFBDVBLFW-VHLOTGQHSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
239000012300 argon atmosphere Substances 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
230000002159 abnormal effect Effects 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
230000004663 cell proliferation Effects 0.000 description 5
239000002808 molecular sieve Substances 0.000 description 5
230000001575 pathological effect Effects 0.000 description 5
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 5
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 5
239000002904 solvent Substances 0.000 description 5
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
238000001816 cooling Methods 0.000 description 4
229960004679 doxorubicin Drugs 0.000 description 4
238000001914 filtration Methods 0.000 description 4
238000001990 intravenous administration Methods 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
POALUPLKPJWUJR-UHFFFAOYSA-N phenyl 1,3-oxazolidine-5-carboxylate Chemical compound O=C(Oc1ccccc1)C1CNCO1 POALUPLKPJWUJR-UHFFFAOYSA-N 0.000 description 4
239000012429 reaction media Substances 0.000 description 4
238000010992 reflux Methods 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
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
229930014667 baccatin III Natural products 0.000 description 3
210000004556 brain Anatomy 0.000 description 3
OZQBDSLJTSETCK-UHFFFAOYSA-N but-3-enoyl but-3-enoate Chemical compound C=CCC(=O)OC(=O)CC=C OZQBDSLJTSETCK-UHFFFAOYSA-N 0.000 description 3
238000007912 intraperitoneal administration Methods 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
238000007911 parenteral administration Methods 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
239000000725 suspension Substances 0.000 description 3
SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
PLRPKVNZGONHKD-UHFFFAOYSA-N 1,3-oxazolidine-5-carboxylic acid Chemical compound OC(=O)C1CNCO1 PLRPKVNZGONHKD-UHFFFAOYSA-N 0.000 description 2
UXTFKIJKRJJXNV-UHFFFAOYSA-N 1-$l^{1}-oxidanylethanone Chemical group CC([O])=O UXTFKIJKRJJXNV-UHFFFAOYSA-N 0.000 description 2
SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 2
IHCCAYCGZOLTEU-UHFFFAOYSA-N 3-furoic acid Chemical compound OC(=O)C=1C=COC=1 IHCCAYCGZOLTEU-UHFFFAOYSA-N 0.000 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 description 2
WHXLTBRGUWTBQP-UZBMNOCMSA-N 7-o-(triethylsilyl) baccatin iii Chemical compound O([C@H]1[C@@H]2[C@]3(OC(C)=O)CO[C@@H]3C[C@@H]([C@]2(C(=O)[C@H](OC(C)=O)C2=C(C)[C@@H](O)C[C@]1(O)C2(C)C)C)O[Si](CC)(CC)CC)C(=O)C1=CC=CC=C1 WHXLTBRGUWTBQP-UZBMNOCMSA-N 0.000 description 2
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
206010048723 Multiple-drug resistance Diseases 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
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
SIOXPEMLGUPBBT-UHFFFAOYSA-N Picolinic acid Natural products OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
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239000002504 physiological saline solution Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
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239000011698 potassium fluoride Substances 0.000 description 1
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238000011321 prophylaxis Methods 0.000 description 1
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150000003242 quaternary ammonium salts Chemical class 0.000 description 1
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OLRJXMHANKMLTD-UHFFFAOYSA-N silyl Chemical compound [SiH3] OLRJXMHANKMLTD-UHFFFAOYSA-N 0.000 description 1
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239000007787 solid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
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150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
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229960001712 testosterone propionate Drugs 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
230000004797 therapeutic response Effects 0.000 description 1
QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
210000001685 thyroid gland Anatomy 0.000 description 1
229960003087 tioguanine Drugs 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
210000001519 tissue Anatomy 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
150000004654 triazenes Chemical class 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
QXTIBZLKQPJVII-UHFFFAOYSA-N triethylsilicon Chemical compound CC[Si](CC)CC QXTIBZLKQPJVII-UHFFFAOYSA-N 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
UGGWPQSBPIFKDZ-KOTLKJBCSA-N vindesine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(N)=O)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1N=C1[C]2C=CC=C1 UGGWPQSBPIFKDZ-KOTLKJBCSA-N 0.000 description 1
229960004355 vindesine Drugs 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
- 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
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur 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)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Oncology (AREA)
Epidemiology (AREA)
Hematology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Epoxy Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Medicines Containing Plant Substances (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

APAP/P/1997/001094A 1995-04-03 1996-04-01 Novel taxoids, preparation thereof and pharmaceutiacl compositions containing same. AP784A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9503868A FR2732342B1 (fr)	1995-04-03	1995-04-03	Nouveaux taxoides, leur preparation et les compositions pharmaceutiques qui les contiennent
PCT/FR1996/000487 WO1996031493A1 (fr)	1995-04-03	1996-04-01	Nouveaux taxoïdes, leur preparation et les compositions pharmaceutiques qui les contiennent

Publications (2)

Publication Number	Publication Date
AP9701094A0 AP9701094A0 (en)	1997-10-31
AP784A true AP784A (en)	1999-11-22

Family

ID=9477663

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
APAP/P/1997/001094A AP784A (en)	1995-04-03	1996-04-01	Novel taxoids, preparation thereof and pharmaceutiacl compositions containing same.

Country Status (32)

Country	Link
US (1)	US5959125A (de)
EP (1)	EP0821680B1 (de)
JP (1)	JPH11504004A (de)
KR (1)	KR19980703520A (de)
CN (1)	CN1073106C (de)
AP (1)	AP784A (de)
AR (1)	AR002730A1 (de)
AT (1)	ATE195940T1 (de)
AU (1)	AU703918B2 (de)
BG (1)	BG62964B1 (de)
BR (1)	BR9604799A (de)
CA (1)	CA2214322C (de)
CZ (1)	CZ287430B6 (de)
DE (1)	DE69610085T2 (de)
DK (1)	DK0821680T3 (de)
EA (1)	EA000726B1 (de)
ES (1)	ES2151155T3 (de)
FR (1)	FR2732342B1 (de)
GE (1)	GEP19991872B (de)
GR (1)	GR3034203T3 (de)
HU (1)	HUP9802042A3 (de)
IL (1)	IL117760A (de)
MX (1)	MX9707427A (de)
NO (1)	NO974563L (de)
NZ (1)	NZ305898A (de)
PL (1)	PL322581A1 (de)
PT (1)	PT821680E (de)
RO (1)	RO115879B1 (de)
SK (1)	SK282047B6 (de)
TW (1)	TW347389B (de)
WO (1)	WO1996031493A1 (de)
ZA (1)	ZA962633B (de)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6495579B1 (en)	1996-12-02	2002-12-17	Angiotech Pharmaceuticals, Inc.	Method for treating multiple sclerosis
FR2764118B1 (fr) *	1997-05-30	2000-08-04	Thomson Csf	Transistor bipolaire stabilise avec elements isolants electriques
US6156789A (en) *	1998-03-17	2000-12-05	Rhone-Poulenc Rorer S.A.	Method for treating abnormal cell proliferation in the brain
CA2365776A1 (en) *	1999-05-03	2000-11-09	Alain Renard	Method for treating abnormal cell proliferation in the brain
MXPA01009921A (es) *	2000-02-02	2003-08-01	Univ Florida State Res Found	Taxanos sustituidos como carbamoiloxilo en c10 como agentes antitumorales.
US6649632B2 (en)	2000-02-02	2003-11-18	Fsu Research Foundation, Inc.	C10 ester substituted taxanes
PL350028A1 (en) *	2000-02-02	2002-10-21	Univ Florida State Res Found	C10 carbonate substituted taxanes as antitumor agents
JP2004339475A (ja) *	2003-02-03	2004-12-02	Merck Patent Gmbh	フッ化物、オキシフッ化物、フルオロ硫化物および／またはオキシフルオロ硫化物に基づく真珠光沢顔料
EP1663153A4 (de) *	2003-05-20	2011-01-05	Aronex Pharmaceuticals Inc	Kombinationschemotherapie mit einem liposomalen platinkomplex
SV2006002010A (es)	2004-02-13	2006-08-23	Univ Florida State Res Found	Taxanos sustituidos con esteres de ciclopentilo en c10
MX2007009748A (es) *	2005-02-14	2007-09-26	Univ Florida State Res Found	Composiciones de taxano sustituidas con esteres ciclopropilicos en c10.
EP2276755A4 (de) *	2008-03-31	2011-05-04	Univ Florida State Res Found	C(10)-ethylester- und c(10)-cyclopropylester-substituierte taxane

Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5254580A (en) *	1993-01-19	1993-10-19	Bristol-Myers Squibb Company	7,8-cyclopropataxanes
FR2698871A1 (fr) *	1992-12-09	1994-06-10	Rhone Poulenc Rorer Sa	Nouveau taxoïdes, leur préparation et les compositions pharmaceutiques qui les contiennent.

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE69333339T2 (de) *	1992-07-01	2004-09-23	Bristol-Myers Squibb Co.	7,8-Zyclopropataxane mit Antitumorwirkung
IL107950A (en) *	1992-12-15	2001-04-30	Upjohn Co	7β, 8β - METHANO-TAXOLS, THEIR PREPARATION AND ANTINEOPLASTIC PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

1995
- 1995-04-03 FR FR9503868A patent/FR2732342B1/fr not_active Expired - Fee Related
1996
- 1996-04-01 GE GEAP19963965A patent/GEP19991872B/en unknown
- 1996-04-01 JP JP8530026A patent/JPH11504004A/ja not_active Ceased
- 1996-04-01 RO RO97-01817A patent/RO115879B1/ro unknown
- 1996-04-01 US US08/930,561 patent/US5959125A/en not_active Expired - Fee Related
- 1996-04-01 MX MX9707427A patent/MX9707427A/es not_active IP Right Cessation
- 1996-04-01 PL PL96322581A patent/PL322581A1/xx unknown
- 1996-04-01 NZ NZ305898A patent/NZ305898A/xx unknown
- 1996-04-01 KR KR1019970706924A patent/KR19980703520A/ko not_active Ceased
- 1996-04-01 TW TW085103805A patent/TW347389B/zh active
- 1996-04-01 HU HU9802042A patent/HUP9802042A3/hu unknown
- 1996-04-01 CA CA002214322A patent/CA2214322C/fr not_active Expired - Fee Related
- 1996-04-01 DK DK96911009T patent/DK0821680T3/da active
- 1996-04-01 PT PT96911009T patent/PT821680E/pt unknown
- 1996-04-01 WO PCT/FR1996/000487 patent/WO1996031493A1/fr not_active Ceased
- 1996-04-01 AP APAP/P/1997/001094A patent/AP784A/en active
- 1996-04-01 SK SK1333-97A patent/SK282047B6/sk unknown
- 1996-04-01 AU AU54028/96A patent/AU703918B2/en not_active Ceased
- 1996-04-01 AT AT96911009T patent/ATE195940T1/de not_active IP Right Cessation
- 1996-04-01 IL IL11776096A patent/IL117760A/en not_active IP Right Cessation
- 1996-04-01 EP EP96911009A patent/EP0821680B1/de not_active Expired - Lifetime
- 1996-04-01 CN CN96192946A patent/CN1073106C/zh not_active Expired - Fee Related
- 1996-04-01 DE DE69610085T patent/DE69610085T2/de not_active Expired - Fee Related
- 1996-04-01 ES ES96911009T patent/ES2151155T3/es not_active Expired - Lifetime
- 1996-04-01 CZ CZ19973109A patent/CZ287430B6/cs not_active IP Right Cessation
- 1996-04-01 BR BR9604799A patent/BR9604799A/pt not_active Application Discontinuation
- 1996-04-01 EA EA199700288A patent/EA000726B1/ru not_active IP Right Cessation
- 1996-04-02 ZA ZA962633A patent/ZA962633B/xx unknown
- 1996-04-03 AR ARP960102049A patent/AR002730A1/es not_active Application Discontinuation
1997
- 1997-10-02 NO NO974563A patent/NO974563L/no not_active Application Discontinuation
- 1997-10-03 BG BG101940A patent/BG62964B1/bg unknown
2000
- 2000-08-31 GR GR20000400100T patent/GR3034203T3/el not_active IP Right Cessation

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2698871A1 (fr) *	1992-12-09	1994-06-10	Rhone Poulenc Rorer Sa	Nouveau taxoïdes, leur préparation et les compositions pharmaceutiques qui les contiennent.
US5254580A (en) *	1993-01-19	1993-10-19	Bristol-Myers Squibb Company	7,8-cyclopropataxanes

Also Published As

Publication number	Publication date
HUP9802042A3 (en)	2001-02-28
AU5402896A (en)	1996-10-23
CA2214322A1 (fr)	1996-10-10
IL117760A0 (en)	1996-08-04
AU703918B2 (en)	1999-04-01
PL322581A1 (en)	1998-02-02
BG62964B1 (bg)	2000-12-29
EA199700288A1 (ru)	1998-04-30
SK282047B6 (sk)	2001-10-08
US5959125A (en)	1999-09-28
NO974563D0 (no)	1997-10-02
GEP19991872B (en)	1999-12-06
GR3034203T3 (en)	2000-11-30
CA2214322C (fr)	2007-01-30
FR2732342A1 (fr)	1996-10-04
IL117760A (en)	2001-11-25
KR19980703520A (ko)	1998-11-05
CZ310997A3 (cs)	1998-01-14
BG101940A (en)	1998-11-30
ES2151155T3 (es)	2000-12-16
TW347389B (en)	1998-12-11
AP9701094A0 (en)	1997-10-31
HUP9802042A2 (hu)	2000-06-28
DE69610085T2 (de)	2001-01-11
CN1179777A (zh)	1998-04-22
MX9707427A (es)	1998-02-28
AR002730A1 (es)	1998-04-29
ATE195940T1 (de)	2000-09-15
FR2732342B1 (fr)	1997-04-30
JPH11504004A (ja)	1999-04-06
WO1996031493A1 (fr)	1996-10-10
EP0821680A1 (de)	1998-02-04
PT821680E (pt)	2000-12-29
DK0821680T3 (da)	2000-11-20
DE69610085D1 (de)	2000-10-05
CN1073106C (zh)	2001-10-17
NO974563L (no)	1997-11-24
BR9604799A (pt)	1999-04-06
EP0821680B1 (de)	2000-08-30
ZA962633B (en)	1996-10-07
NZ305898A (en)	1998-12-23
CZ287430B6 (en)	2000-11-15
EA000726B1 (ru)	2000-02-28
SK133397A3 (en)	1998-02-04
RO115879B1 (ro)	2000-07-28

Publication	Publication Date	Title
AP785A (en)	1999-11-26	Novel taxoids, preparation thereof and pharmaceutical compositions containing same.
US5847170A (en)	1998-12-08	Taxoids, their preparation and pharmaceutical compositions containing them
AU712597B2 (en)	1999-11-11	Novel taxoids, their preparation and pharmaceutical compositions containing them
RU2139864C1 (ru)	1999-10-20	Таксоиды, способы их получения, промежуточные соединения и фармацевтическая композиция
JP4308905B2 (ja)	2009-08-05	新規なタキソイド、その製造及びそれを含有する製薬学的組成物
US6194582B1 (en)	2001-02-27	Taxoids, their preparation and pharmaceutical compositions containing them
AU703918B2 (en)	1999-04-01	New taxoids, their preparation and pharmaceutical compositions containing same
AP1023A (en)	2001-11-16	Taxoids, preparation thereof and pharmaceutical compositions containing same.
US6372780B2 (en)	2002-04-16	Methods of treating cell lines expressing multidrug resistance P-glycoprotein
US5840931A (en)	1998-11-24	Taxoids, their preparation and pharmaceutical compositions containing them
US5777139A (en)	1998-07-07	Taxoids, their preparation and pharmaceutical compositions containing them
MXPA97007427A (en)	1998-02-01	New taxoids, its preparation and the pharmaceutical compositions that contain them
US5968931A (en)	1999-10-19	Taxoids, preparation thereof and pharmaceutical compositions containing same
MXPA96006061A (en)	1998-02-01	Taxoids, its preparation and the pharmaceutical compositions that contain them