CA2368274C - C10 ester substituted taxanes as antitumor agents - Google Patents
C10 ester substituted taxanes as antitumor agents Download PDFInfo
- Publication number
- CA2368274C CA2368274C CA002368274A CA2368274A CA2368274C CA 2368274 C CA2368274 C CA 2368274C CA 002368274 A CA002368274 A CA 002368274A CA 2368274 A CA2368274 A CA 2368274A CA 2368274 C CA2368274 C CA 2368274C
- Authority
- CA
- Canada
- Prior art keywords
- substituted
- thienyl
- furyl
- etcoo
- racoo
- Prior art date
- 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.)
- Expired - Fee Related
Links
- 229940123237 Taxane Drugs 0.000 title claims abstract description 61
- 125000004185 ester group Chemical group 0.000 title abstract 2
- 239000002246 antineoplastic agent Substances 0.000 title description 6
- -1 tert-amyl Chemical group 0.000 claims description 119
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 55
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 50
- 125000002541 furyl group Chemical group 0.000 claims description 49
- 125000001544 thienyl group Chemical group 0.000 claims description 47
- 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 claims description 45
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 42
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 34
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 22
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 19
- 241000124008 Mammalia Species 0.000 claims description 12
- 230000005764 inhibitory process Effects 0.000 claims description 12
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 230000004614 tumor growth Effects 0.000 claims description 11
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 5
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 12
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 5
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 abstract description 24
- 239000000243 solution Substances 0.000 description 88
- 150000001875 compounds Chemical class 0.000 description 69
- 125000000217 alkyl group Chemical group 0.000 description 55
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 49
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- 125000001183 hydrocarbyl group Chemical group 0.000 description 45
- 125000004076 pyridyl group Chemical group 0.000 description 43
- 239000000203 mixture Substances 0.000 description 40
- 230000000259 anti-tumor effect Effects 0.000 description 39
- 125000000304 alkynyl group Chemical group 0.000 description 35
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 15
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- 239000002904 solvent Substances 0.000 description 12
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- 235000019439 ethyl acetate Nutrition 0.000 description 10
- 239000000194 fatty acid Substances 0.000 description 10
- 229930195729 fatty acid Natural products 0.000 description 10
- 238000007911 parenteral administration Methods 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000001241 acetals Chemical class 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 9
- 125000003368 amide group Chemical group 0.000 description 9
- 125000004104 aryloxy group Chemical group 0.000 description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- 125000001072 heteroaryl group Chemical group 0.000 description 9
- 125000001145 hydrido group Chemical group *[H] 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 150000003573 thiols Chemical class 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 229930012538 Paclitaxel Natural products 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 229920002472 Starch Polymers 0.000 description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 229960001592 paclitaxel Drugs 0.000 description 8
- 229920001223 polyethylene glycol Polymers 0.000 description 8
- 125000006239 protecting group Chemical group 0.000 description 8
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
- 239000002552 dosage form Substances 0.000 description 7
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 7
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- 239000008389 polyethoxylated castor oil Substances 0.000 description 7
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- YWLXLRUDGLRYDR-ZHPRIASZSA-N 5beta,20-epoxy-1,7beta,10beta,13alpha-tetrahydroxy-9-oxotax-11-ene-2alpha,4alpha-diyl 4-acetate 2-benzoate Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](O)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 YWLXLRUDGLRYDR-ZHPRIASZSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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- 125000004429 atom Chemical group 0.000 description 6
- 125000001033 ether group Chemical group 0.000 description 6
- 235000011187 glycerol Nutrition 0.000 description 6
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 6
- QUANRIQJNFHVEU-UHFFFAOYSA-N oxirane;propane-1,2,3-triol Chemical compound C1CO1.OCC(O)CO QUANRIQJNFHVEU-UHFFFAOYSA-N 0.000 description 6
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- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
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- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- ICAKDTKJOYSXGC-UHFFFAOYSA-K lanthanum(iii) chloride Chemical compound Cl[La](Cl)Cl ICAKDTKJOYSXGC-UHFFFAOYSA-K 0.000 description 1
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- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001522 polyglycol ester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229940068977 polysorbate 20 Drugs 0.000 description 1
- 229940101027 polysorbate 40 Drugs 0.000 description 1
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- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 230000002633 protecting effect Effects 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- WBHHMMIMDMUBKC-QJWNTBNXSA-M ricinoleate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O WBHHMMIMDMUBKC-QJWNTBNXSA-M 0.000 description 1
- 229940066675 ricinoleate Drugs 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
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- 239000000661 sodium alginate Substances 0.000 description 1
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- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
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- BTURAGWYSMTVOW-UHFFFAOYSA-M sodium dodecanoate Chemical compound [Na+].CCCCCCCCCCCC([O-])=O BTURAGWYSMTVOW-UHFFFAOYSA-M 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229940082004 sodium laurate Drugs 0.000 description 1
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- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
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- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 229940031439 squalene Drugs 0.000 description 1
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
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- 230000003637 steroidlike Effects 0.000 description 1
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- 235000020357 syrup Nutrition 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
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- 235000007586 terpenes Nutrition 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
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- 238000011287 therapeutic dose Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
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- 239000000196 tragacanth Substances 0.000 description 1
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- 125000004665 trialkylsilyl group Chemical group 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
- 150000003641 trioses Chemical class 0.000 description 1
- SCEZSEOTDXHAOD-UHFFFAOYSA-N tris(2,3-dihydroxypropyl) 2-hydroxypropane-1,2,3-tricarboxylate Chemical class OCC(O)COC(=O)CC(O)(C(=O)OCC(O)CO)CC(=O)OCC(O)CO SCEZSEOTDXHAOD-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C MECHNRXZTMCUDQ-RKHKHRCZSA-N 0.000 description 1
- 235000001892 vitamin D2 Nutrition 0.000 description 1
- 239000011653 vitamin D2 Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 235000019386 wax ester Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- CKLHRQNQYIJFFX-UHFFFAOYSA-K ytterbium(III) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Yb+3] CKLHRQNQYIJFFX-UHFFFAOYSA-K 0.000 description 1
Classifications
-
- 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
-
- 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
- A61P35/04—Antineoplastic agents specific for metastasis
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- B65D83/00—Containers or packages with special means for dispensing contents
- B65D83/14—Containers for dispensing liquid or semi-liquid contents by internal gaseous pressure, i.e. aerosol containers comprising propellant
- B65D83/75—Aerosol containers not provided for in groups B65D83/16 - B65D83/74
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Epoxy Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17978200P | 2000-02-02 | 2000-02-02 | |
| US60/179,782 | 2000-02-02 | ||
| PCT/US2001/003623 WO2001057032A1 (en) | 2000-02-02 | 2001-02-02 | C10 ester substituted taxanes as antitumor agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2368274A1 CA2368274A1 (en) | 2001-08-09 |
| CA2368274C true CA2368274C (en) | 2009-10-13 |
Family
ID=22657972
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002368274A Expired - Fee Related CA2368274C (en) | 2000-02-02 | 2001-02-02 | C10 ester substituted taxanes as antitumor agents |
Country Status (25)
| Country | Link |
|---|---|
| EP (1) | EP1165553B1 (enExample) |
| JP (1) | JP2003522172A (enExample) |
| CN (1) | CN1380882A (enExample) |
| AT (1) | ATE432928T1 (enExample) |
| AU (1) | AU782150B2 (enExample) |
| BG (1) | BG64889B1 (enExample) |
| BR (1) | BR0104354A (enExample) |
| CA (1) | CA2368274C (enExample) |
| CZ (1) | CZ20013430A3 (enExample) |
| DE (1) | DE60138853D1 (enExample) |
| GE (1) | GEP20043323B (enExample) |
| HU (1) | HUP0600302A2 (enExample) |
| IL (1) | IL145638A (enExample) |
| MX (1) | MXPA01009905A (enExample) |
| NO (1) | NO327910B1 (enExample) |
| NZ (1) | NZ514382A (enExample) |
| PL (1) | PL202957B1 (enExample) |
| RO (1) | RO121270B1 (enExample) |
| RU (1) | RU2262506C2 (enExample) |
| SK (1) | SK13692001A3 (enExample) |
| TR (1) | TR200102858T1 (enExample) |
| TW (1) | TWI299732B (enExample) |
| UA (1) | UA75039C2 (enExample) |
| WO (1) | WO2001057032A1 (enExample) |
| ZA (1) | ZA200108055B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6649632B2 (en) | 2000-02-02 | 2003-11-18 | Fsu Research Foundation, Inc. | C10 ester substituted taxanes |
| CA2354471A1 (en) * | 2001-07-31 | 2003-01-31 | Florida State University Research Foundation, Inc. | C10 ester substituted taxanes |
| SG129990A1 (en) * | 2001-08-01 | 2007-03-20 | Univ Florida State Res Found | C10 ester substituted taxanes |
| SV2006002010A (es) | 2004-02-13 | 2006-08-23 | Univ Florida State Res Found | Taxanos sustituidos con esteres de ciclopentilo en c10 |
| MX2007009748A (es) * | 2005-02-14 | 2007-09-26 | Univ Florida State Res Found | Composiciones de taxano sustituidas con esteres ciclopropilicos en c10. |
| EP2276755A4 (en) * | 2008-03-31 | 2011-05-04 | Univ Florida State Res Found | C (10) -ETHYESTER- AND C (10) -CYCLOPROPYLESTER-SUBSTITUTED TAXANES |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2601675B1 (fr) * | 1986-07-17 | 1988-09-23 | Rhone Poulenc Sante | Derives du taxol, leur preparation et les compositions pharmaceutiques qui les contiennent |
| US5243045A (en) * | 1991-09-23 | 1993-09-07 | Florida State University | Certain alkoxy substituted taxanes and pharmaceutical compositions containing them |
| US5250683A (en) * | 1991-09-23 | 1993-10-05 | Florida State University | Certain substituted taxanes and pharmaceutical compositions containing them |
| IL108443A0 (en) * | 1993-01-29 | 1994-04-12 | Univ Florida State | C7 taxane derivatives and pharmaceutical compositions containing them |
| ATE209489T1 (de) * | 1993-03-22 | 2001-12-15 | Univ Florida State | Taxane mit pyridyl-substituierter seitenkette |
| DK1227093T3 (da) * | 1993-03-22 | 2005-08-29 | Univ Florida State | Beta-lactamer, der kan anvendes til fremstilling af taxaner med en furyl- eller thienylsubstitueret sidekæde |
| ATE195421T1 (de) * | 1993-03-22 | 2000-09-15 | Univ Florida State | Taxane mit amino-substituierter seitenkette |
| US5475011A (en) * | 1993-03-26 | 1995-12-12 | The Research Foundation Of State University Of New York | Anti-tumor compounds, pharmaceutical compositions, methods for preparation thereof and for treatment |
| WO1996013495A1 (en) * | 1994-10-28 | 1996-05-09 | The Research Foundation Of State University Of New York | Taxoid derivatives, their preparation and their use as antitumor agents |
| US6100411A (en) * | 1994-10-28 | 2000-08-08 | The Research Foundation Of State University Of New York | Taxoid anti-tumor agents and pharmaceutical compositions thereof |
| EP0914116B1 (en) * | 1996-05-22 | 2000-10-11 | Protarga Inc. | Compositions comprising conjugates of cis-docosahexaenoic acid and taxotere |
| US5795909A (en) * | 1996-05-22 | 1998-08-18 | Neuromedica, Inc. | DHA-pharmaceutical agent conjugates of taxanes |
| EP1044971A4 (en) * | 1997-12-19 | 2001-11-07 | Yakult Honsha Kk | TAXAN DERIVATIVES |
| JP2003026673A (ja) * | 1999-03-05 | 2003-01-29 | Asahi Kasei Corp | 骨形成促進剤 |
-
2001
- 2001-02-02 PL PL351380A patent/PL202957B1/pl not_active IP Right Cessation
- 2001-02-02 GE GE4523A patent/GEP20043323B/en unknown
- 2001-02-02 NZ NZ514382A patent/NZ514382A/en unknown
- 2001-02-02 IL IL145638A patent/IL145638A/en not_active IP Right Cessation
- 2001-02-02 AT AT01906971T patent/ATE432928T1/de not_active IP Right Cessation
- 2001-02-02 TR TR2001/02858T patent/TR200102858T1/xx unknown
- 2001-02-02 EP EP01906971A patent/EP1165553B1/en not_active Expired - Lifetime
- 2001-02-02 RO ROA200101083A patent/RO121270B1/ro unknown
- 2001-02-02 AU AU34809/01A patent/AU782150B2/en not_active Ceased
- 2001-02-02 JP JP2001557864A patent/JP2003522172A/ja active Pending
- 2001-02-02 RU RU2001129501/04A patent/RU2262506C2/ru active
- 2001-02-02 DE DE60138853T patent/DE60138853D1/de not_active Expired - Lifetime
- 2001-02-02 HU HU0600302A patent/HUP0600302A2/hu unknown
- 2001-02-02 WO PCT/US2001/003623 patent/WO2001057032A1/en not_active Ceased
- 2001-02-02 CN CN01800568A patent/CN1380882A/zh active Pending
- 2001-02-02 UA UA2001106733A patent/UA75039C2/uk unknown
- 2001-02-02 CZ CZ20013430A patent/CZ20013430A3/cs unknown
- 2001-02-02 MX MXPA01009905A patent/MXPA01009905A/es active IP Right Grant
- 2001-02-02 SK SK1369-2001A patent/SK13692001A3/sk unknown
- 2001-02-02 CA CA002368274A patent/CA2368274C/en not_active Expired - Fee Related
- 2001-02-02 BR BR0104354-4A patent/BR0104354A/pt not_active IP Right Cessation
- 2001-03-27 TW TW090102238A patent/TWI299732B/zh not_active IP Right Cessation
- 2001-10-01 BG BG105965A patent/BG64889B1/bg unknown
- 2001-10-01 NO NO20014754A patent/NO327910B1/no not_active IP Right Cessation
- 2001-10-01 ZA ZA200108055A patent/ZA200108055B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE60138853D1 (de) | 2009-07-16 |
| BG105965A (en) | 2002-07-31 |
| GEP20043323B (en) | 2004-02-10 |
| BR0104354A (pt) | 2002-01-02 |
| PL351380A1 (en) | 2003-04-07 |
| RO121270B1 (ro) | 2007-02-28 |
| NO20014754D0 (no) | 2001-10-01 |
| ATE432928T1 (de) | 2009-06-15 |
| WO2001057032A1 (en) | 2001-08-09 |
| NO327910B1 (no) | 2009-10-19 |
| NO20014754L (no) | 2001-11-29 |
| UA75039C2 (en) | 2006-03-15 |
| SK13692001A3 (sk) | 2002-07-02 |
| CZ20013430A3 (cs) | 2002-04-17 |
| EP1165553A1 (en) | 2002-01-02 |
| PL202957B1 (pl) | 2009-08-31 |
| AU3480901A (en) | 2001-08-14 |
| CA2368274A1 (en) | 2001-08-09 |
| CN1380882A (zh) | 2002-11-20 |
| ZA200108055B (en) | 2003-12-01 |
| JP2003522172A (ja) | 2003-07-22 |
| BG64889B1 (bg) | 2006-08-31 |
| IL145638A0 (en) | 2002-06-30 |
| TR200102858T1 (tr) | 2002-12-23 |
| NZ514382A (en) | 2004-05-28 |
| MXPA01009905A (es) | 2003-08-20 |
| IL145638A (en) | 2011-05-31 |
| EP1165553B1 (en) | 2009-06-03 |
| TWI299732B (en) | 2008-08-11 |
| AU782150B2 (en) | 2005-07-07 |
| HUP0600302A2 (en) | 2006-07-28 |
| RU2262506C2 (ru) | 2005-10-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20150202 |