IL117636A - Taxoids, their preparation and pharmaceutical compositions containing them - Google Patents
Taxoids, their preparation and pharmaceutical compositions containing themInfo
- Publication number
- IL117636A IL117636A IL11763696A IL11763696A IL117636A IL 117636 A IL117636 A IL 117636A IL 11763696 A IL11763696 A IL 11763696A IL 11763696 A IL11763696 A IL 11763696A IL 117636 A IL117636 A IL 117636A
- Authority
- IL
- Israel
- Prior art keywords
- carbon atoms
- radical
- formula
- alkyl
- radical containing
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 4
- -1 alkyl radical Chemical class 0.000 claims abstract description 242
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 193
- 150000003254 radicals Chemical class 0.000 claims abstract description 72
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 48
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 46
- 125000001424 substituent group Chemical group 0.000 claims abstract description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 22
- 125000003118 aryl group Chemical group 0.000 claims abstract description 21
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 20
- 150000002367 halogens Chemical class 0.000 claims abstract description 20
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 16
- 125000005843 halogen group Chemical group 0.000 claims abstract description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 13
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000005840 aryl radicals Chemical class 0.000 claims abstract description 10
- 125000002252 acyl group Chemical group 0.000 claims abstract description 9
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 9
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims abstract description 9
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical group O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 claims abstract description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 239000001301 oxygen Substances 0.000 claims abstract description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 7
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 claims abstract description 7
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 7
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims abstract description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 4
- 125000005239 aroylamino group Chemical group 0.000 claims abstract description 4
- 125000005110 aryl thio group Chemical group 0.000 claims abstract description 4
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 4
- 125000004429 atom Chemical group 0.000 claims abstract description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000005129 aryl carbonyl group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 89
- 229920006395 saturated elastomer Polymers 0.000 claims description 22
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 20
- 150000002148 esters Chemical class 0.000 claims description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 16
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 239000003960 organic solvent Substances 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- 125000006239 protecting group Chemical group 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 239000000725 suspension Substances 0.000 claims description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 11
- 230000009471 action Effects 0.000 claims description 10
- 230000008569 process Effects 0.000 claims 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 claims description 8
- 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 claims description 8
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 230000032050 esterification Effects 0.000 claims description 7
- 238000005886 esterification reaction Methods 0.000 claims description 7
- 150000002170 ethers Chemical class 0.000 claims description 7
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 7
- 150000007522 mineralic acids Chemical class 0.000 claims description 6
- 150000002825 nitriles Chemical class 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical compound O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 claims description 4
- IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical compound C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 0.000 claims description 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000005864 Sulphur Substances 0.000 claims description 4
- 230000003213 activating effect Effects 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-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 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 125000005118 N-alkylcarbamoyl 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
- JAVBBFXUGDCHLZ-UHFFFAOYSA-N 1-$l^{1}-oxidanylpropane Chemical compound CCC[O] JAVBBFXUGDCHLZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic 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
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 238000009903 catalytic hydrogenation reaction Methods 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 group 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
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical class [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 claims 2
- 239000007868 Raney catalyst Substances 0.000 claims 1
- 229910000564 Raney nickel Inorganic materials 0.000 claims 1
- 239000011248 coating agent Substances 0.000 claims 1
- 238000000576 coating method Methods 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- YGAMIEYKXHAVBP-UHFFFAOYSA-N molecular hydrogen;hydrochloride Chemical compound Cl.[H][H] YGAMIEYKXHAVBP-UHFFFAOYSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 132
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- 239000000243 solution Substances 0.000 description 48
- 239000000047 product Substances 0.000 description 40
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 39
- 230000002829 reductive effect Effects 0.000 description 38
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 34
- 239000000203 mixture Substances 0.000 description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 239000006260 foam Substances 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 20
- 239000012153 distilled water Substances 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 18
- 239000012300 argon atmosphere Substances 0.000 description 18
- 238000004587 chromatography analysis Methods 0.000 description 18
- 239000000126 substance Substances 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
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 17
- 235000019341 magnesium sulphate Nutrition 0.000 description 17
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 17
- 239000000377 silicon dioxide Substances 0.000 description 16
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 15
- 239000011521 glass Substances 0.000 description 15
- 239000012074 organic phase Substances 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- 238000003756 stirring Methods 0.000 description 13
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 12
- 238000010828 elution Methods 0.000 description 12
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 11
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 10
- 229910000104 sodium hydride Inorganic materials 0.000 description 10
- 239000012312 sodium hydride Substances 0.000 description 10
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 9
- 206010028980 Neoplasm Diseases 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 229940057995 liquid paraffin Drugs 0.000 description 9
- 239000011780 sodium chloride Substances 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- 101150041968 CDC13 gene Proteins 0.000 description 8
- 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- 229930190007 Baccatin Natural products 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 230000002159 abnormal effect Effects 0.000 description 5
- 235000019270 ammonium chloride Nutrition 0.000 description 5
- 230000004663 cell proliferation Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 230000001575 pathological effect Effects 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 4
- 229960004679 doxorubicin Drugs 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 238000001990 intravenous administration Methods 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- 230000000670 limiting effect Effects 0.000 description 4
- 238000012746 preparative thin layer chromatography Methods 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- 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 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910000040 hydrogen fluoride Inorganic materials 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 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 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-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
- 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
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 description 2
- 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
- 239000002671 adjuvant Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
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- CFCUWKMKBJTWLW-BKHRDMLASA-N mithramycin Chemical compound O([C@@H]1C[C@@H](O[C@H](C)[C@H]1O)OC=1C=C2C=C3C[C@H]([C@@H](C(=O)C3=C(O)C2=C(O)C=1C)O[C@@H]1O[C@H](C)[C@@H](O)[C@H](O[C@@H]2O[C@H](C)[C@H](O)[C@H](O[C@@H]3O[C@H](C)[C@@H](O)[C@@](C)(O)C3)C2)C1)[C@H](OC)C(=O)[C@@H](O)[C@@H](C)O)[C@H]1C[C@@H](O)[C@H](O)[C@@H](C)O1 CFCUWKMKBJTWLW-BKHRDMLASA-N 0.000 description 1
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- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
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- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
- 229960004618 prednisone Drugs 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- CPTBDICYNRMXFX-UHFFFAOYSA-N procarbazine Chemical compound CNNCC1=CC=C(C(=O)NC(C)C)C=C1 CPTBDICYNRMXFX-UHFFFAOYSA-N 0.000 description 1
- 229960000624 procarbazine Drugs 0.000 description 1
- 239000000583 progesterone congener Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
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- ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 1
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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
- 150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
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- 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
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 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
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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
-
- 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
-
- 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)
- Hematology (AREA)
- Oncology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL15937896A IL159378A (en) | 1995-03-27 | 1996-03-24 | Intermediate in the preparation of taxoids |
| IL15937803A IL159378A0 (en) | 1995-03-27 | 2003-12-15 | Intermediate in the preparation of taxoids |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9503545A FR2732340B1 (fr) | 1995-03-27 | 1995-03-27 | Nouveaux taxoides, leur preparation et les compositions pharmaceutiques qui les contiennent |
| FR9515381A FR2742754B1 (fr) | 1995-12-22 | 1995-12-22 | Procede de preparation de taxoides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL117636A0 IL117636A0 (en) | 1996-07-23 |
| IL117636A true IL117636A (en) | 2004-08-31 |
Family
ID=26231838
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL11763696A IL117636A (en) | 1995-03-27 | 1996-03-24 | Taxoids, their preparation and pharmaceutical compositions containing them |
Country Status (41)
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|---|---|
| US (3) | US5889043A (cs) |
| EP (2) | EP0817780B1 (cs) |
| JP (2) | JP2941951B2 (cs) |
| KR (2) | KR100297196B1 (cs) |
| CN (2) | CN1213042C (cs) |
| AP (2) | AP753A (cs) |
| AR (1) | AR001440A1 (cs) |
| AT (2) | ATE188471T1 (cs) |
| AU (2) | AU711227B2 (cs) |
| BG (2) | BG63121B1 (cs) |
| BR (2) | BR9607929A (cs) |
| CA (2) | CA2214319C (cs) |
| CO (1) | CO4700576A1 (cs) |
| CZ (2) | CZ287468B6 (cs) |
| DE (2) | DE69604653T2 (cs) |
| DK (2) | DK0817780T3 (cs) |
| DZ (1) | DZ2009A1 (cs) |
| EA (2) | EA000709B1 (cs) |
| EE (2) | EE03609B1 (cs) |
| ES (2) | ES2140075T3 (cs) |
| GE (2) | GEP20002188B (cs) |
| GR (2) | GR3031526T3 (cs) |
| HU (2) | HU223732B1 (cs) |
| IL (1) | IL117636A (cs) |
| IS (2) | IS2058B (cs) |
| MA (1) | MA23823A1 (cs) |
| MY (1) | MY121225A (cs) |
| NO (2) | NO316607B1 (cs) |
| NZ (2) | NZ304901A (cs) |
| OA (2) | OA10514A (cs) |
| PE (1) | PE51097A1 (cs) |
| PL (2) | PL188284B1 (cs) |
| PT (1) | PT817779E (cs) |
| RO (2) | RO115878B1 (cs) |
| SK (2) | SK281928B6 (cs) |
| TN (1) | TNSN96043A1 (cs) |
| TR (2) | TR199701040T1 (cs) |
| TW (1) | TW394765B (cs) |
| UY (2) | UY24192A1 (cs) |
| WO (2) | WO1996030356A1 (cs) |
| ZA (1) | ZA962399B (cs) |
Families Citing this family (77)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6500858B2 (en) | 1994-10-28 | 2002-12-31 | The Research Foundation Of The State University Of New York | Taxoid anti-tumor agents and pharmaceutical compositions thereof |
| US6495579B1 (en) | 1996-12-02 | 2002-12-17 | Angiotech Pharmaceuticals, Inc. | Method for treating multiple sclerosis |
| US5811452A (en) * | 1997-01-08 | 1998-09-22 | The Research Foundation Of State University Of New York | Taxoid reversal agents for drug-resistance in cancer chemotherapy and pharmaceutical compositions thereof |
| US7288665B1 (en) * | 1997-08-18 | 2007-10-30 | Florida State University | Process for selective derivatization of taxanes |
| FR2771092B1 (fr) * | 1997-11-18 | 1999-12-17 | Rhone Poulenc Rorer Sa | Procede de preparation de derives de la classe des taxoides |
| US6346543B1 (en) * | 1998-08-17 | 2002-02-12 | Aventis Pharma S.A. | Use of a taxoid to treat abnormal cell proliferation in the brain |
| EP0982027A1 (en) * | 1998-08-17 | 2000-03-01 | Aventis Pharma S.A. | Taxoid derivatives for treating abnormal cell proliferation of the brain |
| KR20010079665A (ko) * | 1998-08-20 | 2001-08-22 | 추후제출 | 탁소이드 유도체의 신규 용도 |
| EP0982028A1 (en) * | 1998-08-20 | 2000-03-01 | Aventis Pharma S.A. | New use of taxoid derivatives |
| EP1020188A1 (en) * | 1999-01-13 | 2000-07-19 | Aventis Pharma S.A. | New use of taxoid derivatives |
| CA2368502A1 (en) | 2000-02-02 | 2001-08-09 | Florida State University Research Foundation, Inc. | C10 heterosubstituted acetate taxanes as antitumor agents |
| US6649632B2 (en) | 2000-02-02 | 2003-11-18 | Fsu Research Foundation, Inc. | C10 ester substituted taxanes |
| US8147816B2 (en) * | 2000-08-16 | 2012-04-03 | Encore Health, Llc | Presbyopia treatment by lens alteration |
| HUP0302599A3 (en) | 2000-09-22 | 2005-05-30 | Bristol Myers Squibb Co | Method for reducing toxicity of combined chemotherapic compositions |
| WO2002024178A2 (en) * | 2000-09-22 | 2002-03-28 | Bristol-Myers Squibb Company | Method for reducing toxicity of combined chemotherapies |
| US6593334B1 (en) | 2002-05-02 | 2003-07-15 | The University Of North Carolina At Chapel Hill | Camptothecin-taxoid conjugates as antimitotic and antitumor agents |
| KR102008768B1 (ko) | 2002-09-06 | 2019-08-08 | 인설트 테라페틱스, 인코퍼레이티드 | 공유결합된 치료제 전달을 위한 사이클로덱스트린-기초 중합체 |
| WO2004043390A2 (en) * | 2002-11-08 | 2004-05-27 | Bristol-Myers Squibb Company | Pharmaceutical compositions and methods of using taxane derivatives |
| AU2003239511A1 (en) * | 2003-05-20 | 2004-12-13 | Aronex Pharmaceuticals, Inc. | Combination chemotherapy comprising a liposomal platinum complex |
| US7064980B2 (en) * | 2003-09-17 | 2006-06-20 | Sandisk Corporation | Non-volatile memory and method with bit line coupled compensation |
| FR2859996B1 (fr) * | 2003-09-19 | 2006-02-03 | Aventis Pharma Sa | Solvat acetonique du dimethoxy docetaxel et son procede de preparation |
| GT200500025A (es) * | 2004-02-13 | 2005-09-30 | Taxanos sustituidos con esteres de ciclopentilo en c10 | |
| PE20050693A1 (es) * | 2004-02-13 | 2005-09-27 | Univ Florida State Res Found | Taxanos sustituidos con esteres de ciclopentilo en c10 |
| PE20061090A1 (es) * | 2005-02-14 | 2006-10-12 | Univ Florida State Res Found | Preparaciones de taxanos sustituidos con esteres de ciclopropilo en c10 |
| WO2006102758A1 (en) * | 2005-03-31 | 2006-10-05 | Bioxel Pharma Inc. | Preparation of taxanes from 9-dihydro-13-acetylbaccatin iii |
| CA2627943C (en) * | 2005-11-04 | 2013-12-31 | Bioxel Pharma Inc. | New methods for the preparation of taxanes using chiral auxiliaries |
| US7847111B2 (en) * | 2006-06-19 | 2010-12-07 | Canada Inc. | Semi-synthetic route for the preparation of paclitaxel, docetaxel, and 10-deacetylbaccatin III from 9-dihydro-13-acetylbaccatin III |
| JP2010516625A (ja) | 2007-01-24 | 2010-05-20 | インサート セラピューティクス， インコーポレイテッド | 制御された薬物送達のためのテザー基を有するポリマー−薬物コンジュゲート |
| WO2009006590A2 (en) * | 2007-07-04 | 2009-01-08 | Dr. Reddy's Laboratories Ltd. | Docetaxel process and polymorphs |
| FR2926551A1 (fr) | 2008-01-17 | 2009-07-24 | Aventis Pharma Sa | Formes cristallines du dimethoxy docetaxel et leurs procedes de preparation |
| US8242166B2 (en) * | 2008-03-31 | 2012-08-14 | Florida State University Research Foundation, Inc. | C(10) ethyl ester and C(10) cyclopropyl ester substituted taxanes |
| WO2010019233A1 (en) | 2008-08-11 | 2010-02-18 | Nektar Therapeutics | Multi-arm polymeric alkanoate conjugates |
| FR2945211A1 (fr) | 2009-05-06 | 2010-11-12 | Sanofi Aventis | Combinaison antitumorale comprenant la cabazitaxel et la capecitabine |
| SG10201810928SA (en) | 2009-10-29 | 2019-01-30 | Aventis Pharma Sa | Novel antitumoral use of cabazitaxel |
| CA2781669A1 (en) * | 2009-11-23 | 2011-05-26 | Cerulean Pharma Inc. | Cyclodextrin-based polymers for therapeutic delivery |
| US8791279B2 (en) * | 2010-12-13 | 2014-07-29 | Yung Shin Pharm. Ind. Co., Ltd. | Process for preparing taxoids from baccatin derivatives using lewis acid catalyst |
| WO2012088422A1 (en) | 2010-12-22 | 2012-06-28 | 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 |
| CN102060815B (zh) * | 2010-12-24 | 2012-09-26 | 重庆泰濠制药有限公司 | 一种紫杉烷类化合物的制备方法 |
| WO2012113897A1 (en) | 2011-02-25 | 2012-08-30 | Aventis Pharma S.A. | Antitumoral combination comprising cabazitaxel and cisplatin |
| EP2491925A1 (en) | 2011-02-25 | 2012-08-29 | Aventis Pharma S.A. | Antitumoral combination comprising cabazitaxel and cisplatin |
| EP2620148A1 (en) | 2012-01-27 | 2013-07-31 | Aventis Pharma S.A. | Antitumoral combination comprising cabazitaxel and cisplatin |
| EA023950B1 (ru) | 2011-04-12 | 2016-07-29 | Тева Фармасьютикалз Интернэшнл Гмбх | Твердофазные формы кабазитаксела и способы их получения |
| AU2012290979A1 (en) | 2011-08-02 | 2014-02-13 | Astellas Pharma Inc. | Method for treating cancer by combined use of medicinal agents |
| TWI526437B (zh) * | 2011-09-09 | 2016-03-21 | 台灣神隆股份有限公司 | 卡巴他賽之結晶型 |
| CN104039771B (zh) * | 2011-09-26 | 2017-10-27 | Kabi费森尤斯肿瘤学有限公司 | 包括c(7)‑oh和c(13)‑oh甲硅烷基化或仅c(7)‑oh甲硅烷基化的用于制备卡巴他赛的方法 |
| CN102336726B (zh) * | 2011-09-30 | 2014-11-26 | 重庆泰濠制药有限公司 | 一种卡巴他赛的制备方法 |
| US20130090484A1 (en) * | 2011-10-11 | 2013-04-11 | Scinopharm Taiwan Ltd. | Process for making an intermediate of cabazitaxel |
| CN102408397B (zh) * | 2011-10-19 | 2014-08-20 | 上海贝美医药科技有限公司 | 紫杉烷类衍生物及其制备方法 |
| CN102603724B (zh) * | 2011-10-20 | 2014-02-26 | 江苏红豆杉生物科技股份有限公司 | 二甲氧基紫杉烷类化合物纯化精制的方法 |
| CN102424672A (zh) * | 2011-10-20 | 2012-04-25 | 江苏红豆杉生物科技有限公司 | 脱保护基制备二甲氧基紫杉烷类化合物的方法 |
| CN102516281B (zh) * | 2011-10-20 | 2015-02-04 | 江苏红豆杉生物科技股份有限公司 | 一种10-脱乙酰基巴卡丁iii及其衍生物甲氧基化的方法 |
| CN102417491B (zh) * | 2011-10-31 | 2013-11-06 | 江苏红豆杉生物科技有限公司 | 以10-去乙酰基-巴卡丁iii为原料制备卡巴他赛的方法 |
| CN103906747A (zh) * | 2011-10-31 | 2014-07-02 | 台湾神隆股份有限公司 | 卡巴他赛及其中间体的制备方法 |
| DE112012004569T5 (de) * | 2011-11-01 | 2014-08-14 | Fresenius Kabi Oncology Ltd. | Amorphe Form von Cabazitaxel und Verfahren zum Herstellen davon |
| CN103159705B (zh) * | 2011-12-12 | 2015-05-27 | 福建南方制药股份有限公司 | 卡巴他赛中间体的制备方法 |
| JP6025861B2 (ja) | 2011-12-13 | 2016-11-16 | アベンティス・ファーマ・ソシエテ・アノニム | カバジタキセルの結晶形およびこれを調製するための方法 |
| CN102532064B (zh) * | 2011-12-13 | 2015-06-17 | 重庆泰濠制药有限公司 | 二甲氧基多西他赛的合成方法 |
| CN104583189A (zh) * | 2012-07-31 | 2015-04-29 | 永信药品工业股份有限公司 | 非晶型的卡巴利他索 |
| CN102775434B (zh) * | 2012-08-21 | 2015-04-08 | 江苏红豆杉生物科技股份有限公司 | 一种7,10-二甲氧基紫杉烷化合物中间体的合成方法 |
| CN102775435B (zh) * | 2012-08-21 | 2015-04-08 | 江苏红豆杉生物科技股份有限公司 | 一种用于制备7,10-甲氧基多西他赛的中间体的合成方法 |
| WO2014055493A1 (en) | 2012-10-02 | 2014-04-10 | Cerulean Pharma Inc. | Methods and systems for polymer precipitation and generation of particles |
| CN103804323A (zh) * | 2012-11-14 | 2014-05-21 | 上海希迈医药科技有限公司 | 一种卡巴他赛溶剂化物及其制备方法和应用 |
| KR101407353B1 (ko) | 2012-12-04 | 2014-06-17 | 주식회사 삼양바이오팜 | 10-디아세틸바카틴 iii으로부터 카바지탁셀을 고수율로 제조하는 새로운 방법 및 이를 위한 신규 중간체 |
| EP2743264A1 (en) | 2012-12-13 | 2014-06-18 | INDENA S.p.A. | New crystalline form of cabazitaxel, process for the preparation and pharmaceutical compositions thereof |
| EP2815749A1 (en) | 2013-06-20 | 2014-12-24 | IP Gesellschaft für Management mbH | Solid form of 4-amino-2-(2,6-dioxopiperidine-3-yl)isoindoline-1,3-dione having specified X-ray diffraction pattern |
| EP2865674A1 (en) | 2013-10-23 | 2015-04-29 | INDENA S.p.A. | Crystalline solvate forms of Cabazitaxel |
| EP2865675A1 (en) * | 2013-10-23 | 2015-04-29 | INDENA S.p.A. | A crystalline anhydrous form of Cabazitaxel, process for the preparation and pharmaceutical compositions thereof |
| 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 |
| CN104086514A (zh) * | 2014-06-19 | 2014-10-08 | 上海应用技术学院 | 紫杉醇衍生物及其制备方法 |
| PL3258931T3 (pl) | 2015-02-17 | 2020-12-28 | Erasmus University Medical Center Rotterdam | Zastosowanie kabazitakselu w leczeniu nowotworu złośliwego prostaty |
| EP3093014A1 (en) * | 2015-05-13 | 2016-11-16 | Aventis Pharma S.A. | Cabazitaxel and its use for treating cancer |
| WO2020249507A1 (en) | 2019-06-11 | 2020-12-17 | Indena S.P.A. | Anhydrous crystalline form of cabazitaxel, a process for its preparation and pharmaceutical compositions containing it |
| TWI857119B (zh) | 2019-08-08 | 2024-10-01 | 香港商來凱有限公司 | 治療癌症之方法 |
| EP3808345A1 (en) | 2019-10-15 | 2021-04-21 | Sanofi Mature IP | Cabazitaxel in mcrpc patients previously treated with docetaxel and who failed a prior androgen signaling targeted inhibitor agent |
| EP3797834A1 (en) | 2019-09-25 | 2021-03-31 | Sanofi Mature IP | Cabazitaxel in mcrpc patients previously treated with docetaxel and who failed a prior androgen signaling targeted inhibitor agent |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2629819B1 (fr) | 1988-04-06 | 1990-11-16 | Rhone Poulenc Sante | Procede de preparation de derives de la baccatine iii et de la desacetyl-10 baccatine iii |
| 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 |
| US5739362A (en) | 1991-09-23 | 1998-04-14 | Florida State University | Taxanes having an alkoxy, alkenoxy or aryloxy substituted side-chain and pharmaceutical compositions containing them |
| US5229526A (en) | 1991-09-23 | 1993-07-20 | Florida State University | Metal alkoxides |
| US5489601A (en) | 1991-09-23 | 1996-02-06 | Florida State University | Taxanes having a pyridyl substituted side-chain and pharmaceutical compositions containing them |
| US5319112A (en) | 1992-08-18 | 1994-06-07 | Virgnia Tech Intellectual Properties, Inc. | Method for the conversion of cephalomannine to taxol and for the preparation of N-acyl analogs of taxol |
| FR2696459B1 (fr) | 1992-10-05 | 1994-11-25 | Rhone Poulenc Rorer Sa | Procédé de préparation de dérivés du taxane. |
| NO310238B1 (no) | 1992-12-24 | 2001-06-11 | Bristol Myers Squibb Co | Kjemiske forbindelser og farmasöytisk preparat samt anvendelse av slike preparater |
| ZA94128B (en) * | 1993-02-01 | 1994-08-19 | Univ New York State Res Found | Process for the preparation of taxane derivatives and betalactam intermediates therefor |
| TW467896B (en) | 1993-03-19 | 2001-12-11 | Bristol Myers Squibb Co | Novel β-lactams, methods for the preparation of taxanes and sidechain-bearing taxanes |
| CA2129288C (en) * | 1993-08-17 | 2000-05-16 | Jerzy Golik | Phosphonooxymethyl esters of taxane derivatives |
| CA2179490A1 (en) | 1993-12-21 | 1995-06-29 | Trimurtulu Golakoti | New cryptophycins |
| EP0767786B1 (en) | 1994-06-28 | 1998-09-16 | PHARMACIA & UPJOHN COMPANY | 7-ether-taxol analogs, antineoplastic use and pharmaceutical compositions containing them |
| US6201140B1 (en) | 1994-07-28 | 2001-03-13 | Bristol-Myers Squibb Company | 7-0-ethers of taxane derivatives |
| US5481018A (en) | 1995-03-31 | 1996-01-02 | The Dow Chemical Company | Amino nitrile intermediate for the preparation of alanine diacetic acid |
| FR2745814B1 (fr) | 1996-03-06 | 1998-04-03 | Rhone Poulenc Rorer Sa | Nouveaux taxoides, leur preparation et les compositions pharmaceutiques qui les contiennent |
| FR2771092B1 (fr) | 1997-11-18 | 1999-12-17 | Rhone Poulenc Rorer Sa | Procede de preparation de derives de la classe des taxoides |
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