IL89503A - Taxol derivatives, pharmaceutical compositions containing the same and process for the preparation thereof - Google Patents

Taxol derivatives, pharmaceutical compositions containing the same and process for the preparation thereof

Info

Publication number: IL89503A
Authority: IL; Israel
Prior art keywords: taxol; derivative; salt; carbons; benzyl
Prior art date: 1988-03-07

Application number

IL8950389A

Other languages

English (en)

Other versions

IL89503A0 (en

Original Assignee

Us Health

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.)

1988-03-07

Filing date

1989-03-06

Publication date

1994-02-27

1989-03-06 Application filed by Us Health filed Critical Us Health

1989-09-10 Publication of IL89503A0 publication Critical patent/IL89503A0/xx

1994-02-27 Publication of IL89503A publication Critical patent/IL89503A/en

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 4
238000000034 method Methods 0.000 title abstract description 15
150000004579 taxol derivatives Chemical class 0.000 title abstract description 7
238000002360 preparation method Methods 0.000 title description 4
230000008569 process Effects 0.000 title description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
230000000118 anti-neoplastic effect Effects 0.000 claims abstract description 7
RCINICONZNJXQF-MZXODVADSA-N taxol Chemical class 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 claims description 24
229930012538 Paclitaxel Natural products 0.000 claims description 22
229960001592 paclitaxel Drugs 0.000 claims description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 11
-1 dimethylamino-ethyl Chemical group 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
150000002148 esters Chemical class 0.000 claims description 3
125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 2
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims description 2
150000004820 halides Chemical class 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 2
ZDXPYRJPNDTMRX-GSVOUGTGSA-N D-glutamine Chemical compound OC(=O)[C@H](N)CCC(N)=O ZDXPYRJPNDTMRX-GSVOUGTGSA-N 0.000 claims 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
101100220369 Mus musculus Csgalnact1 gene Proteins 0.000 claims 1
150000001875 compounds Chemical class 0.000 description 18
239000002253 acid Substances 0.000 description 15
206010028980 Neoplasm Diseases 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
241001465754 Metazoa Species 0.000 description 8
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 7
239000000243 solution Substances 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
238000012360 testing method Methods 0.000 description 6
239000000047 product Substances 0.000 description 5
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
150000008064 anhydrides Chemical class 0.000 description 4
230000000259 anti-tumor effect Effects 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
159000000000 sodium salts Chemical class 0.000 description 4
RBNOJYDPFALIQZ-LAVNIZMLSA-N 2'-succinyltaxol 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](OC(=O)CCC(O)=O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RBNOJYDPFALIQZ-LAVNIZMLSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
208000001382 Experimental Melanoma Diseases 0.000 description 3
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
201000011510 cancer Diseases 0.000 description 3
230000008859 change Effects 0.000 description 3
239000003814 drug Substances 0.000 description 3
229940079593 drug Drugs 0.000 description 3
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
239000000463 material Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
230000003389 potentiating effect Effects 0.000 description 3
239000002904 solvent Substances 0.000 description 3
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
229960000549 4-dimethylaminophenol Drugs 0.000 description 2
206010006187 Breast cancer Diseases 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
230000037396 body weight Effects 0.000 description 2
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
230000001472 cytotoxic effect Effects 0.000 description 2
IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
239000000376 reactant Substances 0.000 description 2
238000012216 screening Methods 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
150000003900 succinic acid esters Chemical class 0.000 description 2
229940014800 succinic anhydride Drugs 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
231100000331 toxic Toxicity 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 1
LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
JVKRKMWZYMKVTQ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JVKRKMWZYMKVTQ-UHFFFAOYSA-N 0.000 description 1
WNLWBCIUNCAMPH-UHFFFAOYSA-N 2-n,2-n-dimethylpropane-1,2-diamine Chemical compound NCC(C)N(C)C WNLWBCIUNCAMPH-UHFFFAOYSA-N 0.000 description 1
JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 1
YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
101150065749 Churc1 gene Proteins 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
102100038239 Protein Churchill Human genes 0.000 description 1
241001116500 Taxus Species 0.000 description 1
241000202349 Taxus brevifolia Species 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
102000004243 Tubulin Human genes 0.000 description 1
108090000704 Tubulin Proteins 0.000 description 1
230000004913 activation Effects 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
239000003080 antimitotic agent Substances 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
238000013459 approach Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
238000003556 assay Methods 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
210000000481 breast Anatomy 0.000 description 1
229910001424 calcium ion Inorganic materials 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
231100000433 cytotoxic Toxicity 0.000 description 1
229940043237 diethanolamine Drugs 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical class OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
ZOMZNNQGMGBLHO-UHFFFAOYSA-N heptane-1,5-diamine Chemical compound CCC(N)CCCCN ZOMZNNQGMGBLHO-UHFFFAOYSA-N 0.000 description 1
XTBMQKZEIICCCS-UHFFFAOYSA-N hexane-1,5-diamine Chemical compound CC(N)CCCCN XTBMQKZEIICCCS-UHFFFAOYSA-N 0.000 description 1
XPXMKIXDFWLRAA-UHFFFAOYSA-N hydrazinide Chemical compound [NH-]N XPXMKIXDFWLRAA-UHFFFAOYSA-N 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000012750 in vivo screening Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
230000010534 mechanism of action Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
229910000069 nitrogen hydride Inorganic materials 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
239000008149 soap solution Substances 0.000 description 1
RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
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
230000001225 therapeutic effect Effects 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
238000002424 x-ray crystallography Methods 0.000 description 1

Classifications

- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- 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

Landscapes

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

IL8950389A 1988-03-07 1989-03-06 Taxol derivatives, pharmaceutical compositions containing the same and process for the preparation thereof IL89503A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/165,173 US4942184A (en)	1988-03-07	1988-03-07	Water soluble, antineoplastic derivatives of taxol

Publications (2)

Publication Number	Publication Date
IL89503A0 IL89503A0 (en)	1989-09-10
IL89503A true IL89503A (en)	1994-02-27

Family

ID=22597770

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL8950389A IL89503A (en)	1988-03-07	1989-03-06	Taxol derivatives, pharmaceutical compositions containing the same and process for the preparation thereof

Country Status (9)

Country	Link
US (1)	US4942184A (de)
EP (1)	EP0406274B1 (de)
JP (1)	JP2680152B2 (de)
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Families Citing this family (182)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4960790A (en) *	1989-03-09	1990-10-02	University Of Kansas	Derivatives of taxol, pharmaceutical compositions thereof and methods for the preparation thereof
MY110249A (en) *	1989-05-31	1998-03-31	Univ Florida State	Method for preparation of taxol using beta lactam
US5278324A (en) *	1990-08-28	1994-01-11	Virginia Tech Intellectual Properties, Inc.	Water soluble derivatives of taxol
US5059699A (en) *	1990-08-28	1991-10-22	Virginia Tech Intellectual Properties, Inc.	Water soluble derivatives of taxol
US5380916A (en) *	1990-11-02	1995-01-10	University Of Florida	Method for the isolation and purification of taxane derivatives
US5194635A (en) *	1991-03-18	1993-03-16	Virginia Tech Intellectual Properties, Inc.	Rearranged taxol compounds and method of using in testing of in vivo activity
US6150398A (en) *	1991-05-08	2000-11-21	The United States Of America As Represented By The Department Of Health And Human Services	Methods for the treatment of cancer
US5334093A (en) *	1991-05-10	1994-08-02	Deere & Company	Detachable covers for an axial separator
CA2072400C (en)	1991-07-05	2003-08-19	Jayaprakash B. Nair	Supercritical extraction of taxanes
US5489601A (en) *	1991-09-23	1996-02-06	Florida State University	Taxanes having a pyridyl substituted side-chain and pharmaceutical compositions containing them
US5430160A (en) *	1991-09-23	1995-07-04	Florida State University	Preparation of substituted isoserine esters using β-lactams and metal or ammonium alkoxides
US6495704B1 (en)	1991-09-23	2002-12-17	Florida State University	9-desoxotaxanes and process for the preparation of 9-desoxotaxanes
US5283253A (en) *	1991-09-23	1994-02-01	Florida State University	Furyl or thienyl carbonyl substituted taxanes and pharmaceutical compositions containing them
US5728850A (en) *	1991-09-23	1998-03-17	Florida State University	Taxanes having a butenyl substituted side-chain and pharmaceutical compositions containing them
US5998656A (en) *	1991-09-23	1999-12-07	Florida State University	C10 tricyclic taxanes
US6018073A (en) *	1991-09-23	2000-01-25	Florida State University	Tricyclic taxanes having an alkoxy, alkenoxy or aryloxy substituted side-chain and pharmaceutical compositions containing them
US5654447A (en) *	1991-09-23	1997-08-05	Florida State University	Process for the preparation of 10-desacetoxybaccatin III
IL103191A (en) *	1991-09-23	2001-07-24	Univ Florida State	Semi-synthesis of taxane derivatives using metal alkoxides and beta-lactams and intermediates thereof
US5710287A (en) *	1991-09-23	1998-01-20	Florida State University	Taxanes having an amino substituted side-chain and pharmaceutical compositions containing them
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
US5714513A (en) *	1991-09-23	1998-02-03	Florida State University	C10 taxane derivatives and pharmaceutical compositions
US5227400A (en) *	1991-09-23	1993-07-13	Florida State University	Furyl and thienyl substituted taxanes and pharmaceutical compositions containing them
US5338872A (en) *	1993-01-15	1994-08-16	Florida State University	Process for the preparation of 10-desacetoxybaccatin III and 10-desacetoxytaxol and derivatives thereof
US6794523B2 (en)	1991-09-23	2004-09-21	Florida State University	Taxanes having t-butoxycarbonyl substituted side-chains and pharmaceutical compositions containing them
US5350866A (en) *	1991-09-23	1994-09-27	Bristol-Myers Squibb Company	10-desacetoxytaxol derivatives
US5274124A (en) *	1991-09-23	1993-12-28	Florida State University	Metal alkoxides
US5250683A (en) *	1991-09-23	1993-10-05	Florida State University	Certain substituted taxanes and pharmaceutical compositions containing them
US5243045A (en) *	1991-09-23	1993-09-07	Florida State University	Certain alkoxy substituted taxanes and pharmaceutical compositions containing them
US5284865A (en) *	1991-09-23	1994-02-08	Holton Robert A	Cyclohexyl substituted taxanes and pharmaceutical compositions containing them
US5728725A (en) *	1991-09-23	1998-03-17	Florida State University	C2 taxane derivaties and pharmaceutical compositions containing them
US5229526A (en) *	1991-09-23	1993-07-20	Florida State University	Metal alkoxides
US6335362B1 (en)	1991-09-23	2002-01-01	Florida State University	Taxanes having an alkyl substituted side-chain and pharmaceutical compositions containing them
US6028205A (en) *	1991-09-23	2000-02-22	Florida State University	C2 tricyclic taxanes
US7074945B2 (en) *	1991-09-23	2006-07-11	Florida State University	Metal alkoxide taxane derivatives
US5811447A (en) *	1993-01-28	1998-09-22	Neorx Corporation	Therapeutic inhibitor of vascular smooth muscle cells
US6515009B1 (en) *	1991-09-27	2003-02-04	Neorx Corporation	Therapeutic inhibitor of vascular smooth muscle cells
DK0552041T3 (da) *	1992-01-15	2000-10-09	Squibb & Sons Inc	Enzymatiske fremgangsmåder til spaltning af enantiomerblandinger af forbindelser, der er nyttige som mellemprodukter ved fr
US5272171A (en) *	1992-02-13	1993-12-21	Bristol-Myers Squibb Company	Phosphonooxy and carbonate derivatives of taxol
US5445809A (en) *	1992-03-03	1995-08-29	Research And Development Institute At Montana State University	Production of taxol from the yew tree
US5451392A (en) *	1992-03-03	1995-09-19	The Research And Development Institute At Montana State University	Production of taxol
US5254703A (en) *	1992-04-06	1993-10-19	Florida State University	Semi-synthesis of taxane derivatives using metal alkoxides and oxazinones
JPH069600A (ja) *	1992-05-06	1994-01-18	Bristol Myers Squibb Co	タクソールのベンゾエート誘導体
FR2691460B1 (fr) *	1992-05-21	1994-07-22	Rhone Poulenc Rorer Sa	Nouveaux derives du taxane, leur preparation et les compositions qui les contiennent.
JPH08500973A (ja) *	1992-05-21	1996-02-06	ザペンステイトリサーチファウンデーション	タキソール、関連タキサン及び他の新規な抗癌／抗ウイルス性化合物原料としてのイチイ培養組織
US5364947A (en) *	1992-07-02	1994-11-15	Hauser Chemical Research, Inc.	Process for separating cephalomannine from taxol using ozone and water-soluble hydrazines or hydrazides
US5614549A (en) *	1992-08-21	1997-03-25	Enzon, Inc.	High molecular weight polymer-based prodrugs
WO1994005282A1 (en) *	1992-09-04	1994-03-17	The Scripps Research Institute	Water soluble taxol derivatives
FR2696464B1 (fr) *	1992-10-05	1994-11-10	Rhone Poulenc Rorer Sa	Nouveau procédé d'estérification de la baccatine III et de la désacétyl-10 baccatine III.
US5411984A (en) *	1992-10-16	1995-05-02	Virginia Tech Intellectual Properties, Inc.	Water soluble analogs and prodrugs of taxol
ATE319698T1 (de) *	1992-11-13	2006-03-15	Univ Florida State	Taxane mit alkyl substituierte seiten-kette und diese enthaltende pharmazeutische zusammenstellungen
AU5612694A (en) *	1992-11-27	1994-06-22	Napro Biotherapeutics, Inc.	Injectable composition
US5356927A (en) *	1992-12-02	1994-10-18	Thomas Jefferson University	Methods of treating plasmodium and babesia parasitic infections
US5631278A (en) *	1992-12-02	1997-05-20	Thomas Jefferson University	Methods of killing protozoal parasites
US5279949A (en) *	1992-12-07	1994-01-18	Board Of Trustees Operating Michigan State University	Process for the isolation and purification of taxol and taxanes from Taxus spp
IL107950A (en)	1992-12-15	2001-04-30	Upjohn Co	7β, 8β - METHANO-TAXOLS, THEIR PREPARATION AND ANTINEOPLASTIC PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
US5973160A (en)	1992-12-23	1999-10-26	Poss; Michael A.	Methods for the preparation of novel sidechain-bearing taxanes
RU2136673C1 (ru) *	1992-12-24	1999-09-10	Бристоль-Мейерз Сквибб Компани	Фосфонооксиметиловые эфиры таксановых производных, промежуточные соединения, противоопухолевая фармацевтическая композиция, способ ингибирования роста опухоли у млекопитающих
US5646176A (en)	1992-12-24	1997-07-08	Bristol-Myers Squibb Company	Phosphonooxymethyl ethers of taxane derivatives
MX9308012A (es) *	1992-12-24	1994-08-31	Bristol Myers Squibb Co	Eteres fosfonooximetilicos de derivados de taxano, solubles en agua y composiciones farmaceuticas que los incluyen.
IL108444A0 (en) *	1993-01-29	1994-04-12	Univ Florida State	C2 taxane derivatives and pharmaceutical compositions containing them
US6066747A (en) *	1993-03-05	2000-05-23	Florida State University	Process for the preparation of 9-desoxotaxanes
US6710191B2 (en)	1993-03-05	2004-03-23	Florida State University	9β-hydroxytetracyclic taxanes
DE69430797T2 (de) *	1993-03-05	2003-02-27	Florida State University, Tallahassee	C9 taxanderivate und diese enthaltende pharmazeutische zusammensetzungen
US5547981A (en) *	1993-03-09	1996-08-20	Enzon, Inc.	Taxol-7-carbazates
WO1994020089A1 (en) *	1993-03-09	1994-09-15	Enzon, Inc.	Taxol-based compositions with enhanced bioactivity
CA2092271C (en) *	1993-03-09	2009-10-13	Eddie Reed	Use of g-csf for treating taxol side-effects
DE69425563T2 (de) *	1993-03-22	2001-01-25	Florida State University, Tallahassee	Taxane mit amino-substituierter seitenkette
DK0690867T3 (da) *	1993-03-22	2003-06-10	Univ Florida State	Taxaner med furyl- eller thienylsubstitueret sidekæde
US5336684A (en) *	1993-04-26	1994-08-09	Hauser Chemical Research, Inc.	Oxidation products of cephalomannine
IT1261667B (it) *	1993-05-20	1996-05-29		Tassano ad attivita' antitumorale.
ES2205663T3 (es) *	1993-06-11	2004-05-01	PHARMACIA & UPJOHN COMPANY	Uso antineoplasico de delta 6,7-taxoles y composiciones farmaceuticas que los contienen.
US5468769A (en) *	1993-07-15	1995-11-21	Abbott Laboratories	Paclitaxel derivatives
CA2472404A1 (en)	1993-07-19	1995-02-02	Angiotech Pharmaceuticals, Inc.	Combination of stent and anti-angiogenic factor
EP1118325B2 (de) *	1993-07-29	2010-01-06	The United States of America, represented by the Secretary, Department of Health and Human Services	Verwendung von Paclitaxel und seinen Derivaten zur Herstellung eines Medikaments für die Behandlung von Restenose
CA2129288C (en) *	1993-08-17	2000-05-16	Jerzy Golik	Phosphonooxymethyl esters of taxane derivatives
US5880131A (en) *	1993-10-20	1999-03-09	Enzon, Inc.	High molecular weight polymer-based prodrugs
US5965566A (en) *	1993-10-20	1999-10-12	Enzon, Inc.	High molecular weight polymer-based prodrugs
AU8052194A (en) *	1993-10-20	1995-05-08	Enzon, Inc.	2'- and/or 7- substituted taxoids
US5415869A (en) *	1993-11-12	1995-05-16	The Research Foundation Of State University Of New York	Taxol formulation
AU698382B2 (en)	1994-01-11	1998-10-29	Scripps Research Institute, The	Chemical switching of taxo-diterpenoids between low solubility active forms and high solubility inactive forms
DE69527346T2 (de)	1994-01-11	2003-02-13	The Scripps Research Institute, La Jolla	Sich selbst bildende taxo-diterpenoid nanostrukturen
US5731334A (en) *	1994-01-11	1998-03-24	The Scripps Research Institute	Method for treating cancer using taxoid onium salt prodrugs
IL127598A (en) *	1994-01-28	2003-04-10	Upjohn Co	Process for preparing isotaxol analogs
GB9405400D0 (en) *	1994-03-18	1994-05-04	Erba Carlo Spa	Taxane derivatives
US5508447A (en) *	1994-05-24	1996-04-16	Board Of Regents, The University Of Texas System	Short synthetic route to taxol and taxol derivatives
CA2192373A1 (en) *	1994-06-09	1995-12-14	Hirofumi Terasawa	Deacetoxytaxol derivative
USRE38424E1 (en)	1994-11-21	2004-02-10	The United States Of America As Represented By The Department Of Health And Human Services	Method for treating taxol side-effects with G-CSF
US5489589A (en) *	1994-12-07	1996-02-06	Bristol-Myers Squibb Company	Amino acid derivatives of paclitaxel
CA2170661A1 (en)	1995-03-22	1996-09-23	John K. Thottathil	Novel methods for the preparation of taxanes using oaxzolidine intermediates
US5801191A (en) *	1995-06-01	1998-09-01	Biophysica Foundation	Taxoids
AU716005B2 (en)	1995-06-07	2000-02-17	Cook Medical Technologies Llc	Implantable medical device
EP0871620A4 (de) *	1995-09-11	1999-10-27	Enzymed Inc	Biokatalytische methoden zur sythese und zur identifikation von biologisch aktiven verbindungen
US5654448A (en) *	1995-10-02	1997-08-05	Xechem International, Inc.	Isolation and purification of paclitaxel from organic matter containing paclitaxel, cephalomannine and other related taxanes
US5854278A (en) *	1995-12-13	1998-12-29	Xechem International, Inc.	Preparation of chlorinated paclitaxel analogues and use thereof as antitumor agents
US5807888A (en) *	1995-12-13	1998-09-15	Xechem International, Inc.	Preparation of brominated paclitaxel analogues and their use as effective antitumor agents
US5840748A (en) *	1995-10-02	1998-11-24	Xechem International, Inc.	Dihalocephalomannine and methods of use therefor
US6177456B1 (en)	1995-10-02	2001-01-23	Xechem International, Inc.	Monohalocephalomannines having anticancer and antileukemic activity and method of preparation therefor
US5760072A (en) *	1995-12-29	1998-06-02	Pharmachemie B.V.	Paclitaxel prodrugs, method for preparation as well as their use in selective chemotherapy
US6441025B2 (en) *	1996-03-12	2002-08-27	Pg-Txl Company, L.P.	Water soluble paclitaxel derivatives
CN1304058C (zh)	1996-03-12	2007-03-14	Pg－Txl有限公司	水溶性紫杉醇产品
AU724499B2 (en)	1996-05-06	2000-09-21	Florida State University	1-deoxy baccatin III, 1-deoxy taxol and 1-deoxy taxol analogs and method for the preparation thereof
ATE223889T1 (de)	1996-05-08	2002-09-15	Upjohn Co	Oxazolidinester
US5919815A (en) *	1996-05-22	1999-07-06	Neuromedica, Inc.	Taxane compounds and compositions
DE69734060T2 (de)	1996-05-24	2006-06-29	Angiotech Pharmaceuticals, Inc., Vancouver	Zubereitungen und verfahren zur behandlung oder prävention von krankheiten der körperpassagewege
US5635531A (en) *	1996-07-08	1997-06-03	Bristol-Myers Squibb Company	3'-aminocarbonyloxy paclitaxels
AU710156B2 (en) *	1996-07-15	1999-09-16	Kabushiki Kaisha Yakult Honsha	Taxane derivatives and drugs containing the same
GB9705903D0 (en)	1997-03-21	1997-05-07	Elliott Gillian D	VP22 Proteins and uses thereof
JPH1192468A (ja) *	1997-09-17	1999-04-06	Yakult Honsha Co Ltd	新規なタキサン誘導体
IL131217A0 (en) *	1998-03-10	2001-01-28	Napro Biotherapeutics Inc	Novel methods and compositions for delivery of taxanes
US5981564A (en) *	1998-07-01	1999-11-09	Universite Laval	Water-soluble derivatives of paclitaxel, method for producing same and uses thereof
US6303589B1 (en)	1998-12-08	2001-10-16	Micro Flo Company	Pentacyclic triterpenes
US20030054977A1 (en) *	1999-10-12	2003-03-20	Cell Therapeutics, Inc.	Manufacture of polyglutamate-therapeutic agent conjugates
US20020077290A1 (en) *	2000-03-17	2002-06-20	Rama Bhatt	Polyglutamic acid-camptothecin conjugates and methods of preparation
US6395771B1 (en) *	2000-05-31	2002-05-28	Dabur Research Foundation	Paclitaxel derivatives for the treatment of cancer
US6638742B1 (en)	2000-07-07	2003-10-28	University Of Portland	Methods for obtaining taxanes
CZ2003837A3 (cs) *	2000-09-22	2004-12-15	Bristol-Myers Squibb Company	Způsob pro snížení toxicity při kombinovaných chemoterapiích
US6919370B2 (en) *	2000-11-28	2005-07-19	Transform Pharmaceuticals, Inc.	Pharmaceutical formulations comprising paclitaxel, derivatives, and pharmaceutically acceptable salts thereof
CA2440935A1 (en)	2001-03-13	2002-09-19	Richard Liggins	Micellar drug delivery vehicles and precursors thereto and uses thereof
US20030157170A1 (en) *	2001-03-13	2003-08-21	Richard Liggins	Micellar drug delivery vehicles and precursors thereto and uses thereof
DE60220519T2 (de) *	2001-04-20	2007-09-27	The University Of British Columbia, Vancouver	Mizellares arzneistoffverabreichungssystem für hydrophobe arzneistoffe
EP2295081B1 (de) *	2001-06-26	2018-10-31	Amgen Inc.	Antikörper gegen OPGL
WO2003026581A2 (en) *	2001-09-26	2003-04-03	Intermune, Inc.	Pharmaceutical compositions and methods for treating cancer
US6710195B2 (en) *	2001-11-26	2004-03-23	Supergen, Inc.	Method for preparing and using polyoxyethylated castor oil in pharmaceutical compositions
WO2003045357A1 (en) *	2001-11-27	2003-06-05	Transform Pharmaceuticals, Inc.	Oral pharmaceutical formulations comprising paclitaxel, derivatives and methods of administration thereof
PL368945A1 (en) *	2001-11-30	2005-04-04	Bristol-Myers Squibb Company	Paclitaxel solvates
US20030216758A1 (en) *	2001-12-28	2003-11-20	Angiotech Pharmaceuticals, Inc.	Coated surgical patches
US7176325B2 (en) *	2002-04-05	2007-02-13	Natural Pharmaceuticals, Inc.	Selective acylation of secondary hydroxyl groups
US20040047835A1 (en) *	2002-09-06	2004-03-11	Cell Therapeutics, Inc.	Combinatorial drug therapy using polymer drug conjugates
WO2004037311A2 (en) *	2002-10-21	2004-05-06	Kensey Nash Corporation	Device and methods for sequential, regional delivery of multiple cytotoxic agents
AU2003300076C1 (en)	2002-12-30	2010-03-04	Angiotech International Ag	Drug delivery from rapid gelling polymer composition
WO2004060403A2 (en) *	2003-01-06	2004-07-22	Angiochem Inc.	Aprotinin and anglos as carriers across the blood-brain barrier
PT1720540E (pt)	2004-02-18	2008-09-10	Gpc Biotech Ag	Métodos de tratamento de tumores resistentes ou refractários
US7989490B2 (en)	2004-06-02	2011-08-02	Cordis Corporation	Injectable formulations of taxanes for cad treatment
US7846940B2 (en) *	2004-03-31	2010-12-07	Cordis Corporation	Solution formulations of sirolimus and its analogs for CAD treatment
US8003122B2 (en) *	2004-03-31	2011-08-23	Cordis Corporation	Device for local and/or regional delivery employing liquid formulations of therapeutic agents
EP1750673B1 (de) *	2004-05-17	2009-12-02	Tekmira Pharmaceuticals Corporation	Liposomale formulierungen mit dihydrosphingomyelin und verfahren zu ihrer verwendung
EP2298291A3 (de)	2004-06-18	2011-08-03	Agennix USA Inc.	Kinasehemmer zur Behandlung von Krebs
US20060135468A1 (en)	2004-09-02	2006-06-22	Bionaut Pharmaceuticals, Inc.	Treatment of refractory cancers using NA+/K+ ATPase inhibitors
USH2260H1 (en)	2005-02-17	2011-07-05	Angiotech International Ag	Stents combined with paclitaxel derivatives
RU2408605C2 (ru) *	2005-02-18	2011-01-10	Анджиокем Инк.	Полипептид, способный преодолевать гематоэнцефалический барьер, и его конъюгат
US20090016959A1 (en) *	2005-02-18	2009-01-15	Richard Beliveau	Delivery of antibodies to the central nervous system
ES2744225T3 (es)	2005-07-15	2020-02-24	Angiochem Inc	Uso de polipéptidos de aprotinina como portadores en conjugados farmacéuticos
US20070073385A1 (en) *	2005-09-20	2007-03-29	Cook Incorporated	Eluting, implantable medical device
WO2007067498A1 (en) *	2005-12-06	2007-06-14	Cell Therapeutics, Inc.	Estrogen cancer therapy
PL217731B1 (pl)	2006-06-01	2014-08-29	Tomasz Byrski	Sposób wykrywania genetycznie uwarunkowanej obniżonej odpowiedzi na chemioterapię cytostatykiem taksanowym, zastosowanie mutacji założycielskiej oraz zestawu do wykrywania takiej odpowiedzi
WO2008005284A2 (en)	2006-06-30	2008-01-10	Cook Incorporated	Methods of manufacturing and modifying taxane coatings for implantable medical devices
US20080241215A1 (en) *	2007-03-28	2008-10-02	Robert Falotico	Local vascular delivery of probucol alone or in combination with sirolimus to treat restenosis, vulnerable plaque, aaa and stroke
US9365634B2 (en) *	2007-05-29	2016-06-14	Angiochem Inc.	Aprotinin-like polypeptides for delivering agents conjugated thereto to tissues
US8420110B2 (en)	2008-03-31	2013-04-16	Cordis Corporation	Drug coated expandable devices
US8409601B2 (en)	2008-03-31	2013-04-02	Cordis Corporation	Rapamycin coated expandable devices
MX2010011165A (es) *	2008-04-10	2011-02-22	Abraxis Bioscience Llc	Composiciones de derivados de taxano hidrofobos y sus usos.
MX355683B (es) *	2008-04-18	2018-04-26	Angiochem Inc	Composiciones farmacéuticas de paclitaxel, análogos de paclitaxel o conjugados de paclitaxel, y métodos relacionados de preparación y uso.
US8273404B2 (en) *	2008-05-19	2012-09-25	Cordis Corporation	Extraction of solvents from drug containing polymer reservoirs
KR101975843B1 (ko)	2008-05-23	2019-05-09	더 유니버시티 오브 브리티쉬 콜롬비아	리포좀 나노입자에 사용하기 위한 변형된 약물
AU2009282413B2 (en) *	2008-08-11	2014-07-17	Nektar Therapeutics	Multi-arm polymeric alkanoate conjugates
US8642063B2 (en)	2008-08-22	2014-02-04	Cook Medical Technologies Llc	Implantable medical device coatings with biodegradable elastomer and releasable taxane agent
US9198968B2 (en)	2008-09-15	2015-12-01	The Spectranetics Corporation	Local delivery of water-soluble or water-insoluble therapeutic agents to the surface of body lumens
WO2010043049A1 (en)	2008-10-15	2010-04-22	Angiochem Inc.	Etoposide and doxorubicin conjugates for drug delivery
CA2740316A1 (en)	2008-10-15	2010-04-22	Angiochem Inc.	Conjugates of glp-1 agonists and uses thereof
CA2745524C (en) *	2008-12-05	2020-06-09	Angiochem Inc.	Conjugates of neurotensin or neurotensin analogs and uses thereof
US8853353B2 (en)	2008-12-17	2014-10-07	Angiochem, Inc.	Membrane type-1 matrix metalloprotein inhibitors and uses thereof
MX2011009413A (es)	2009-03-11	2011-10-21	Ambit Biosciences Corp	Combinacion de una indazolilaminopirrolotriazina y taxano para tratamiento contra cancer.
MX2011011023A (es)	2009-04-20	2012-01-20	Angiochem Inc	Tratamiento de cancer de ovarios usando un agente anti-cancer conjugado con un analogo de angiopep-2.
RU2012103240A (ru)	2009-07-02	2013-08-10	Ангиокем Инк.	Мультимерные пептидные конъюгаты и их применение
JP2013530993A (ja)	2010-07-02	2013-08-01	アンジオケムインコーポレーテッド	治療用コンジュゲートのための短く且つｄ−アミノ酸を含有するポリペプチドおよびその使用
WO2012088422A1 (en)	2010-12-22	2012-06-28	Nektar Therapeutics	Multi-arm polymeric prodrug conjugates of taxane-based compounds
WO2012088445A1 (en)	2010-12-22	2012-06-28	Nektar Therapeutics	Multi-arm polymeric prodrug conjugates of cabazitaxel-based compounds
US20120303115A1 (en)	2011-05-25	2012-11-29	Dadino Ronald C	Expandable devices coated with a rapamycin composition
US20120302954A1 (en)	2011-05-25	2012-11-29	Zhao Jonathon Z	Expandable devices coated with a paclitaxel composition
CN108686203A (zh)	2012-04-04	2018-10-23	哈洛齐梅公司	使用抗透明质酸剂和肿瘤靶向紫杉烷的组合疗法
US9956385B2 (en)	2012-06-28	2018-05-01	The Spectranetics Corporation	Post-processing of a medical device to control morphology and mechanical properties
AR099812A1 (es)	2014-03-21	2016-08-17	Abbvie Inc	Anticuerpos y conjugados de anticuerpo y fármaco anti-egfr
EP3307326B9 (de)	2015-06-15	2021-02-24	Angiochem Inc.	Verfahren zur behandlung von leptomeningealer karzinomatose
AU2016326747A1 (en)	2015-09-25	2018-03-01	Zy Therapeutics Inc.	Drug formulation based on particulates comprising polysaccharide-vitamin conjugate
US20200147235A1 (en)	2016-06-08	2020-05-14	Abbvie Inc.	Anti-cd98 antibodies and antibody drug conjugates
JP2019524651A (ja)	2016-06-08	2019-09-05	アッヴィ・インコーポレイテッド	抗ｃｄ９８抗体及び抗体薬物コンジュゲート
AU2017279550A1 (en)	2016-06-08	2019-01-03	Abbvie Inc.	Anti-B7-H3 antibodies and antibody drug conjugates
MX2018015285A (es)	2016-06-08	2019-09-18	Abbvie Inc	Anticuerpos anti-b7-h3 y conjugados de anticuerpo y farmaco.
WO2017214322A1 (en)	2016-06-08	2017-12-14	Abbvie Inc.	Anti-b7-h3 antibodies and antibody drug conjugates
US20190351031A1 (en)	2018-05-16	2019-11-21	Halozyme, Inc.	Methods of selecting subjects for combination cancer therapy with a polymer-conjugated soluble ph20
CN111662250B (zh) *	2019-03-05	2023-12-15	中国医学科学院药物研究所	季铵化修饰紫杉烷衍生物、其药物组合物、其合成途径和用途
AR124681A1 (es)	2021-01-20	2023-04-26	Abbvie Inc	Conjugados anticuerpo-fármaco anti-egfr

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4206221A (en) *	1979-01-03	1980-06-03	The United States Of America As Represented By The Secretary Of Agriculture	Cephalomannine and its use in treating leukemic tumors
FR2601676B1 (fr) *	1986-07-17	1988-09-23	Rhone Poulenc Sante	Procede de preparation du taxol et du desacetyl-10 taxol
FR2601675B1 (fr) *	1986-07-17	1988-09-23	Rhone Poulenc Sante	Derives du taxol, leur preparation et les compositions pharmaceutiques qui les contiennent
FR2629818B1 (fr) *	1988-04-06	1990-11-16	Centre Nat Rech Scient	Procede de preparation du taxol

1988
- 1988-03-07 US US07/165,173 patent/US4942184A/en not_active Expired - Lifetime
1989
- 1989-02-28 WO PCT/US1989/000810 patent/WO1989008453A1/en not_active Ceased
- 1989-02-28 DE DE68917129T patent/DE68917129T2/de not_active Expired - Lifetime
- 1989-02-28 AU AU32861/89A patent/AU620605B2/en not_active Expired
- 1989-02-28 AT AT89903659T patent/ATE109002T1/de not_active IP Right Cessation
- 1989-02-28 EP EP89903659A patent/EP0406274B1/de not_active Expired - Lifetime
- 1989-02-28 JP JP1503332A patent/JP2680152B2/ja not_active Expired - Lifetime
- 1989-03-06 CA CA000592894A patent/CA1330436C/en not_active Expired - Lifetime
- 1989-03-06 IL IL8950389A patent/IL89503A/en unknown

Also Published As

Publication number	Publication date
US4942184A (en)	1990-07-17
DE68917129T2 (de)	1995-03-02
CA1330436C (en)	1994-06-28
IL89503A0 (en)	1989-09-10
JPH03505725A (ja)	1991-12-12
EP0406274B1 (de)	1994-07-27
AU620605B2 (en)	1992-02-20
EP0406274A1 (de)	1991-01-09
WO1989008453A1 (en)	1989-09-21
AU3286189A (en)	1989-10-05
ATE109002T1 (de)	1994-08-15
JP2680152B2 (ja)	1997-11-19
EP0406274A4 (en)	1991-08-28
DE68917129D1 (de)	1994-09-01

Legal Events

Date	Code	Title	Description
1999-08-17	KB	Patent renewed
2003-05-29	KB	Patent renewed

Publication	Publication Date	Title
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