JPH10500981A - 新規のタキソイド類、それらの製造、およびそれらを含む製薬学的組成物 - Google Patents

新規のタキソイド類、それらの製造、およびそれらを含む製薬学的組成物

Info

Publication number: JPH10500981A
Authority: JP; Japan
Prior art keywords: group; carbon atoms; alkyl; substituted; group containing
Prior art date: 1994-06-09
Legal status (The legal status 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 status listed.): Pending

Application number

JP8500462A

Other languages

English (en)

Japanese (ja)

Inventor

エルベブシヤール，

ジヤン−ドミニクブルザ，

アランコメルソン，

コリヌテリエ，

マルテイヌズツコ，

Original Assignee

ローン−プーラン・ロレ・ソシエテ・アノニム

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.)

1994-06-09

Filing date

1995-06-07

Publication date

1998-01-27

1995-06-07 Application filed by ローン−プーラン・ロレ・ソシエテ・アノニム filed Critical ローン−プーラン・ロレ・ソシエテ・アノニム

1998-01-27 Publication of JPH10500981A publication Critical patent/JPH10500981A/ja

Status Pending legal-status Critical Current

Links

239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 5
238000002360 preparation method Methods 0.000 title claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 127
125000000217 alkyl group Chemical group 0.000 claims abstract description 69
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 54
125000003118 aryl group Chemical group 0.000 claims abstract description 46
125000003545 alkoxy group Chemical group 0.000 claims abstract description 41
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 33
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 32
238000000034 method Methods 0.000 claims abstract description 24
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 19
125000003342 alkenyl group Chemical group 0.000 claims abstract description 17
125000004423 acyloxy group Chemical group 0.000 claims abstract description 16
125000000304 alkynyl group Chemical group 0.000 claims abstract description 15
125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 12
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 9
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
150000001602 bicycloalkyls Chemical group 0.000 claims abstract description 8
239000001257 hydrogen Substances 0.000 claims abstract description 8
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
229910052799 carbon Inorganic materials 0.000 claims abstract description 7
125000000468 ketone group Chemical group 0.000 claims abstract description 3
-1 1-piperazinyl group Chemical group 0.000 claims description 166
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 30
239000000203 mixture Substances 0.000 claims description 30
125000005843 halogen group Chemical group 0.000 claims description 26
125000004429 atom Chemical group 0.000 claims description 24
229920006395 saturated elastomer Polymers 0.000 claims description 22
125000006239 protecting group Chemical group 0.000 claims description 17
125000004663 dialkyl amino group Chemical group 0.000 claims description 15
239000003960 organic solvent Substances 0.000 claims description 15
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
125000002252 acyl group Chemical group 0.000 claims description 12
125000004442 acylamino group Chemical group 0.000 claims description 10
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
125000003282 alkyl amino group Chemical group 0.000 claims description 8
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 7
125000003710 aryl alkyl group Chemical group 0.000 claims description 7
125000005117 dialkylcarbamoyl group Chemical group 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 7
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 6
150000001875 compounds Chemical class 0.000 claims description 6
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 6
125000000175 2-thienyl group Chemical group S1C([*])=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
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 5
125000005239 aroylamino group Chemical group 0.000 claims description 5
125000004104 aryloxy group Chemical group 0.000 claims description 5
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
125000003884 phenylalkyl group Chemical group 0.000 claims description 4
KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 3
CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims description 3
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 3
125000005110 aryl thio group Chemical group 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
150000001540 azides Chemical class 0.000 claims description 3
125000000524 functional group Chemical group 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
125000004434 sulfur atom Chemical group 0.000 claims description 3
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical class OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 3
125000001963 4 membered heterocyclic group Chemical group 0.000 claims description 2
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 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
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
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
DYMRYCZRMAHYKE-UHFFFAOYSA-N n-diazonitramide Chemical compound [O-][N+](=O)N=[N+]=[N-] DYMRYCZRMAHYKE-UHFFFAOYSA-N 0.000 claims description 2
125000000547 substituted alkyl group Chemical group 0.000 claims description 2
125000000335 thiazolyl group Chemical group 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
231100000331 toxic Toxicity 0.000 claims description 2
230000002588 toxic effect Effects 0.000 claims description 2
229940111121 antirheumatic drug quinolines Drugs 0.000 claims 1
150000003248 quinolines Chemical class 0.000 claims 1
230000000259 anti-tumor effect Effects 0.000 abstract description 3
230000000719 anti-leukaemic effect Effects 0.000 abstract description 2
125000001624 naphthyl group Chemical group 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 94
239000000047 product Substances 0.000 description 76
239000000243 solution Substances 0.000 description 48
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 42
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 37
ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 36
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 33
230000002829 reductive effect Effects 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 28
229940123237 Taxane Drugs 0.000 description 28
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 27
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
239000006260 foam Substances 0.000 description 22
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 18
239000000377 silicon dioxide Substances 0.000 description 18
238000001035 drying Methods 0.000 description 16
239000012074 organic phase Substances 0.000 description 15
238000011282 treatment Methods 0.000 description 14
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 13
229910052943 magnesium sulfate Inorganic materials 0.000 description 13
235000019341 magnesium sulphate Nutrition 0.000 description 13
239000011780 sodium chloride Substances 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
150000002148 esters Chemical class 0.000 description 11
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 10
238000004587 chromatography analysis Methods 0.000 description 10
238000003756 stirring Methods 0.000 description 10
239000002253 acid Substances 0.000 description 9
230000000704 physical effect Effects 0.000 description 9
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
206010028980 Neoplasm Diseases 0.000 description 8
230000009471 action Effects 0.000 description 8
238000010828 elution Methods 0.000 description 8
239000002609 medium Substances 0.000 description 8
238000004062 sedimentation Methods 0.000 description 8
238000006467 substitution reaction Methods 0.000 description 8
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
235000019270 ammonium chloride Nutrition 0.000 description 7
239000003480 eluent Substances 0.000 description 7
IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 7
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
125000001931 aliphatic group Chemical group 0.000 description 5
239000012300 argon atmosphere Substances 0.000 description 5
230000010261 cell growth Effects 0.000 description 5
239000012071 phase Substances 0.000 description 5
238000001291 vacuum drying Methods 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
239000011701 zinc Substances 0.000 description 5
229910052725 zinc Inorganic materials 0.000 description 5
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
230000002159 abnormal effect Effects 0.000 description 4
DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 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
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
230000032050 esterification Effects 0.000 description 4
238000005886 esterification reaction Methods 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
229910052731 fluorine Inorganic materials 0.000 description 4
239000011737 fluorine Substances 0.000 description 4
238000007912 intraperitoneal administration Methods 0.000 description 4
150000007522 mineralic acids Chemical class 0.000 description 4
150000002825 nitriles Chemical class 0.000 description 4
150000007524 organic acids Chemical class 0.000 description 4
230000001575 pathological effect Effects 0.000 description 4
239000012429 reaction media Substances 0.000 description 4
208000024891 symptom Diseases 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 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
230000010933 acylation Effects 0.000 description 3
238000005917 acylation reaction Methods 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
150000007530 organic bases Chemical class 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
230000004044 response Effects 0.000 description 3
239000002904 solvent Substances 0.000 description 3
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 3
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 2
OZUCDJFMALKZOS-UHFFFAOYSA-N 2-(butoxycarbonylamino)-2-hydroxy-3-phenylpropanoic acid Chemical group CCCCOC(=O)NC(O)(C(O)=O)CC1=CC=CC=C1 OZUCDJFMALKZOS-UHFFFAOYSA-N 0.000 description 2
ZHWDQYCJDJUYPP-UHFFFAOYSA-N 2-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid Chemical group OC(=O)C1OC(C(=O)OCCCC)(C=2C=CC(OC)=CC=2)NC1C1=CC=CC=C1 ZHWDQYCJDJUYPP-UHFFFAOYSA-N 0.000 description 2
JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
HJCUTNIGJHJGCF-UHFFFAOYSA-N 9,10-dihydroacridine Chemical compound C1=CC=C2CC3=CC=CC=C3NC2=C1 HJCUTNIGJHJGCF-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
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 2
239000004593 Epoxy Substances 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
206010033128 Ovarian cancer Diseases 0.000 description 2
206010061535 Ovarian neoplasm Diseases 0.000 description 2
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SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
239000002671 adjuvant Substances 0.000 description 2
150000003927 aminopyridines Chemical class 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
239000002246 antineoplastic agent Substances 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
210000004556 brain Anatomy 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
210000004027 cell Anatomy 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 2
208000029742 colonic neoplasm Diseases 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
239000010949 copper Substances 0.000 description 2
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical class [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
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URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
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229910052717 sulfur Inorganic materials 0.000 description 1
239000000725 suspension Substances 0.000 description 1
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DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 description 1
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229960001278 teniposide Drugs 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
150000003512 tertiary amines Chemical class 0.000 description 1
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229960001712 testosterone propionate Drugs 0.000 description 1
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QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 description 1
210000001541 thymus gland Anatomy 0.000 description 1
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AYNNSCRYTDRFCP-UHFFFAOYSA-N triazene Chemical compound NN=N AYNNSCRYTDRFCP-UHFFFAOYSA-N 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 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
231100000397 ulcer Toxicity 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
210000003462 vein Anatomy 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
239000011787 zinc oxide Substances 0.000 description 1

Classifications

- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/14—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Epoxy Compounds (AREA)

JP8500462A 1994-06-09 1995-06-07 新規のタキソイド類、それらの製造、およびそれらを含む製薬学的組成物 Pending JPH10500981A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
FR9407052A FR2721026B1 (fr)	1994-06-09	1994-06-09	Nouveaux taxoïdes, leur préparation et les compositions pharmaceutiques qui les contiennent.
FR94/07052		1994-06-09
PCT/FR1995/000738 WO1995033739A1 (fr)	1994-06-09	1995-06-07	Nouveaux taxoides, leur preparation et les compositions pharmaceutiques qui les contiennent

Publications (1)

Publication Number	Publication Date
JPH10500981A true JPH10500981A (ja)	1998-01-27

Family

ID=9464036

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP8500462A Pending JPH10500981A (ja)	1994-06-09	1995-06-07	新規のタキソイド類、それらの製造、およびそれらを含む製薬学的組成物

Country Status (6)

Country	Link
EP (1)	EP0764156A1 (fr)
JP (1)	JPH10500981A (fr)
AU (1)	AU2742095A (fr)
CA (1)	CA2190657A1 (fr)
FR (1)	FR2721026B1 (fr)
WO (1)	WO1995033739A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2721024B1 (fr) *	1994-06-09	1996-07-12	Rhone Poulenc Rorer Sa	Nouveaux 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
CA2109861C (fr) *	1992-12-04	1999-03-16	Shu-Hui Chen	Paclitaxels modifies en 6,7
ES2205663T3 (es) *	1993-06-11	2004-05-01	PHARMACIA & UPJOHN COMPANY	Uso antineoplasico de delta 6,7-taxoles y composiciones farmaceuticas que los contienen.

1994
- 1994-06-09 FR FR9407052A patent/FR2721026B1/fr not_active Expired - Fee Related
1995
- 1995-06-07 JP JP8500462A patent/JPH10500981A/ja active Pending
- 1995-06-07 EP EP95922572A patent/EP0764156A1/fr not_active Ceased
- 1995-06-07 AU AU27420/95A patent/AU2742095A/en not_active Abandoned
- 1995-06-07 CA CA002190657A patent/CA2190657A1/fr not_active Abandoned
- 1995-06-07 WO PCT/FR1995/000738 patent/WO1995033739A1/fr not_active Ceased

Also Published As

Publication number	Publication date
EP0764156A1 (fr)	1997-03-26
CA2190657A1 (fr)	1995-12-14
AU2742095A (en)	1996-01-04
WO1995033739A1 (fr)	1995-12-14
FR2721026B1 (fr)	1996-07-12
FR2721026A1 (fr)	1995-12-15

Publication	Publication Date	Title
JP3953106B2 (ja)	2007-08-08	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
JP3790826B2 (ja)	2006-06-28	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
US5847170A (en)	1998-12-08	Taxoids, their preparation and pharmaceutical compositions containing them
JPH08504425A (ja)	1996-05-14	新規タキソイド、それらの製造及びそれらを含む製薬学的組成物
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
US6372780B2 (en)	2002-04-16	Methods of treating cell lines expressing multidrug resistance P-glycoprotein
JP2000506158A (ja)	2000-05-23	タキソイド類、それらの製造及びそれらを含有する製薬学的組成物
US5959125A (en)	1999-09-28	Taxoids, preparation thereof, and pharmaceutical compositions containing same
RU2153496C2 (ru)	2000-07-27	Таксоиды, способ их получения и фармацевтическая композиция на их основе
JPH10500979A (ja)	1998-01-27	新規タキソイド類、その製造およびそれらを含む製薬学的組成物
SK157196A3 (en)	1997-06-04	Taxoids, preparation and pharmaceutical compositions containing them
US5968931A (en)	1999-10-19	Taxoids, preparation thereof and pharmaceutical compositions containing same
JPH10500981A (ja)	1998-01-27	新規のタキソイド類、それらの製造、およびそれらを含む製薬学的組成物
HK1017895B (en)	2003-08-29	Novel taxoids, preparation thereof and pharmaceutical compositions containing same
MXPA96006227A (en)	1998-02-01	Novedous taxoids your preparation and the pharmaceutical compositions that contain them
MXPA96006061A (en)	1998-02-01	Taxoids, its preparation and the pharmaceutical compositions that contain them